My Top 30 Favorite Episodes of the Simpsons, Part 3 (10-1)

As I said in my first blog, there are three fandoms that I am super-obsessed with: Pro wrestling, Star Wars, and the Simpsons. This is something that will likely never change, and I never want it to change. I love the world of Star Wars and I love the professional wrestling business. However, one love came first, and that’s the love I share with Springfield’s most famous family. I’ve watched the show ever since it was a short on the Tracy Ullman Show. I remember watching “Simpsons Roasting on an Open Fire” when it first aired, and all the subsequent episodes that followed. For those keeping score, there are now 523 episodes of the show that have aired.

With so many episodes in the can, it was difficult to narrow down my top 10, let alone my top 30, but I’ve done it. The task is complete, and parts 1 and 2 have been written. It’s time to put this blog to bed, and finish the countdown.

Get ready, Simpsons fans, here they are:




10. Itchy & Scratchy Land (Season 6, Episode 4)


I love satire, especially when it’s at the expense of the Walt Disney Company. Don’t get me wrong, I’m a big Disney fan, and I was an employee of the mouse for six years. But Disney is a company that, at times, deserves to be mocked. Especially the theme parks. Well, here’s the Simpsons take on a popular characterized theme park, where nothing could possib-lie go wrong.

Err, possibly go wrong.

That’s the first thing that’s ever gone wrong.

Bart and Lisa convince their parents to take their family vacation to Itchy & Scratchy Land, where the kids can have fun while the parents hang out on Parent’s Island. Marge is cautious, because she already planned a trip to the bird sanctuary, and always ends up embarrassed after every trip. However, she relents, and the family is off on vacation! After parking in the Itchy Lot, and traveling via helicopter to the park itself (Jurassic Park style), the family experiences all the magic of the park, with some of the BEST Disney jokes of all time. However, after Bart and Homer are arrested for harassing the characters, the trip turns dark as the robots revolt due to chaos theory (did John Hammond design this place?) The family manages to stop the killer robots, and proclaim it the best vacation ever.


I don’t even know where to begin with this one. Everything is a shot at Disney, from the rides to the animatronics, and even the attitude of the employees. They rip off Disney films with Itchy & Scratchy versions, and even have the “Rogers Myers Experience” which is a direct ripoff of the One Man’s Dream museum at Disney’s Hollywood Studios. They have a 12:00 robot parade, an area just for parents that spoofs Disney’s former Pleasure Island, and even rip on the antics of costume characters. Among the Disney gags is the classic Bort License Plate joke, a staple of Simpsons fandom, and Maggie suffering in the ball pit of doom. The jokes fly hard in this one, and while it’s a great episode for the average Simpsons fan, it’s downright perfect for those of us who love Disney.


Next time you’re bored and want to watch an episode of the Simpsons, may I kindly suggest taking a trip back to Itchy & Scratchy Land? I don’t think you’ll leave disappointed.


9. You Only Move Twice (Season 8, Episode 2)

Scorpio flamethrower

What if your boss was the nicest guy in the world, but was actually a supervillain bent on global domination? Okay, so all Hank Scorpio wanted was the East Coast, but still, he treated his employees like gold!

Homer is offered an exciting new job in a town called Cypress Creek, a planned community that is too good to be true. Homer excels at his new job, and is beloved by his new perfect boss, Hank Scorpio, who seems like the perfect guy to work for. Voiced brilliantly by one of the Simpsons best (and oldest) guest stars, Albert Brooks (Nemo’s dad is a villain!!!), Hank Scorpio became one of the greatest one-time Simpsons characters ever with his one appearance. While Homer is happy, the rest of the family isn’t. Marge becomes so bored by all the automatic features in the house, that she develops a drinking problem (in her eyes anyway). Lisa is allergic to everything around her, and Bart is put into a remedial class simply because the school is better than Springfield Elementary. They begrudgingly tell Homer they want to return to Springfield, which he does for the good of his family. However, Hank Scorpio buys Homer a farewell gift to help him get closer to his dream of owning the Dallas Cowboys – the Denver Broncos (d’oh!)

As I mentioned earlier, this episode is made by the Hank Scorpio character. He’s a jovial and witty fast-talking boss who really values his employees, and treats them like family. Unfortunately, he’s a diabolical villain too, and is on a mission to seize control of the East Coast. The family lives in luxury, but all experience downfalls that make them miss their old home and old life. Their side stories are the perfect counter to Homer’s new life. It’s a good message that Homer will still choose his family’s happiness over his own, even when everything is going his way. The James Bond references get mixed in, and the final result is a great Simpsons episode.


No Mr. Bont, I expect you to die and for it to be a cheap funeral. You’re gonna die now!


8. Marge Vs. The Monorail (Season 4, Episode 12)


It’s the monorail episode.

The town acquires $3 million after fining Mr. Burns, and holds a meeting to decide how to spend it. A mysterious salesman named Lyle Lanley shows up, and tells the citizens that he can get them on the map by selling them a monorail. After all, it worked for Brockway, Ogdenville, and North Haverbrook. The town builds the monorail system, and Homer gets a job as a monorail pilot. The inaugural ride is celebrated with a guest appearance by Leonard Nimoy, but it’s soon discovered that the train was built was faulty equipment. Lyle skips town with the money, and Marge goes to North Haverbrook to get help. She brings a citizen back with her, as Lyle’s plane makes an unscheduled stop in one of the town he ruined (where he’s presumably beaten to death). Homer uses the giant ‘M’ on the monorail as an anchor to save the day, as Springfield celebrates yet another failed venture, like their popsicle stick skyscraper, 300-ft. magnifying glass, and escalator to nowhere.

It’s the monorail episode. It has an iconic song, is fondly remembered by fans, and was written by Conan O’Brien. I have nothing else to say that can possibly add to this episode’s greatness.

Well, sir, there’s nothing on earth like a genuine, bona-fide, electrified, six-car monorail!


7. Homer’s Enemy (Season 8, Episode 23)


Doug Walker, better known as the Nostalgia Critic, summed up this episode perfectly when he said it was one of the darkest Simpsons episodes of all time, and that’s what made it so great.

Meet Frank Grimes, a man who has struggled through literally everything in life, and worked hard every single day for the very little he has. Mr. Burns is inspired by this, and hires him as part of the nuclear power plant team. Frank then meets Homer Simpson, the lazy oaf who has had everything handed to him in life. Frank is enraged at Homer’s mere existence, and after Homer’s incompetence gets him in trouble, Frank proclaims them as enemies. Homer is saddened by this, and tries to make amends with Frank by inviting him over to his house. This makes matters worse, as Grimes becomes baffled at Homer’s big house, beautiful family, and achievements such as outer space travel and his Grammy award. Grimes tries to make the whole plant see what a buffoon Homer is by tricking him into entering a power plant design contest for children, but when Homer wins and his peers cheer him on, Grimes slips into insanity. His resulting rampage to be oafish like Homer costs him his life, and the episode ends with everyone laughing at Homer sleeping DURING THE FUNERAL.


What an incredible episode. Frank Grimes, much like Hank Scorpio, becomes one of the best – if not THE best – one time Simpsons character ever. The episode tells a story that many of us can relate to. Sometimes, hard-working individuals get screwed over, while lazy stupid people succeed at everything. The writers make you really feel bad for Frank Grimes, while still not managing to really like him, because he can be a total dick too. His death is surprising, but how they close the episode is downright mean. It’s by far one of their darkest episodes, and it’s absolutely amazing.


Poor Grimey. Poor, poor, Grimey.


6. Lisa the Vegetarian (Season 7, Episode 5)


While Homer is by far my favorite character, and Bart is somewhat of an icon to the show (especially in its early years), one of the least appreciated characters, and one of the best written, has to be Lisa. She’s the intelligent middle child whose gifts go overlooked, and whose moral beliefs get her into trouble. This episode marks a serious turning point in her character development. It’s probably the best Lisa-centric episode there is.

The family travels to Storytime Village, a fairy tale themed park for babies, so Maggie can enjoy something for once. While visiting, Lisa falls in love with a baby lamb at the petting zoo area. That night, as the family sits down to a dinner of lamb chops, Lisa becomes conflicted about eating the animal. She becomes uncomfortable with worm dissection in class, and upset that the school offers no vegetarian selection. As she struggles to come to terms with her newfound vegetarianism, Homer plans a huge barbecue party to counter the Flanders’ family reunion. Lisa tries to protest Homer’s party, but her pleas go ignored. She finally snaps, and ruins the party by driving off Homer’s stuffed pig. She ends up storming out of the house, and fails to fight temptation after seeing meat everywhere. She succumbs and eats one of Apu’s hot dogs, but they turn out to be tofu, as Apu is also a vegetarian. With a little helpful advice from Apu and Paul & Linda McCartney, telling Lisa to tolerate others rather than judge them, she and Homer forgive each other and Homer gives her a veggie-back ride home.

lisa vegetarian

This episode works for two reasons: its character development, and its hilarity level. Lisa is by far the most complex character of the family, and she often makes decisions that last for the long-run, such as becoming a Buddhist. This episode marks a big turning point for her, as she renounces eating meat and becomes a champion of animal rights. On the other side, the jokes come at you fast and hard, and they all hit the mark. The conversation at the dinner table, all the way to the BBQ antics, cement this episode as one of the best in the series. Few episodes manage to be laugh-out-loud hilarious, and manage to develop a major character in a serious and meaningful way. This episode hits the mark on every joke. It’s one of the best.


Come to Homer’s BBBQ. The extra B is for BYOBB.

What’s that extra B for?

That’s a typo.


5. Homer the Great (Season 6, Episode 12)


It’s the Stonecutters episode. Seriously, do I need to deliver the monorail spiel here too? I guess I already did.

Homer becomes curious as to why Lenny and Carl are never around Wednesday nights, and why they always seem to have nicer stuff than him. He stalks them to a secret society called the Stonecutters, and becomes anxious to join. He gets in as the son of a Stonecutter, and becomes enamored with his new life. After all, all this society does is get drunk and act like morons. However, at a great rib feast, he destroys their sacred parchment, and is banished. But, shocking, it’s discovered that he’s actually the Chosen One, whom the sacred parchment said would lead them to glory! Homer abuses his power, until he realizes how much it’s isolating him from everyone. Lisa advises him to get the group to help other people instead, which makes Homer feel rewarded, but the society itself doesn’t want that. After all, they just want to act like morons and drink beer. So they form their own secret society, the Ancient Mystic Society of No Homers.


Featuring the best musical number on the show next to the Monorail Song, this episode has it all. It’s one of the funniest episodes, with some of the best gags, and tells a story that really hits home. Organizations like this exist, with the people contributing literally NOTHING to society. This is the Simpsons take on how ridiculous this concept really is. The perks they get for being members are outrageous, and the fact that all they do is act like a fraternity despite being “ancient and great” is a brilliant concept. Of course, the Chosen One gag that leads to the Stonecutters downfall is the real highlight, especially the No Homers gag. Homer is once again reminded that’s family over…well, stupid bullshit like this. It’s an episode that works on every level and is a classic by every sense of the word.

Did I mention Number One is voiced by Patrick Stewart?

Who controls the British crown? Who keeps the metric system down? We do, we do!
Who keeps Atlantis off the maps? Who keeps the Martians under wraps? We do, we do!
Who holds back the electric car? Who makes Steve Guttenberg a star? We do, we do!
Who robs cavefish of their sight? Who rigs every Oscar night? We do, we do, we do!


4. Cape Feare (Season 5, Episode 2)


While Bart may have been the rapscallion icon of the early 90s, he was little more than a modern day, raunchier Dennis the Menace. However, there is one thing about Bart that defines him more than anything else – his moral enemy, the articulate, brilliant, and downright insane Sideshow Bob. This is the quintessential Sideshow Bob episode, and it’s AMAZING.

Bart is starting to receive death threats in the mail, written in human blood. They are coming from Sideshow Bob, the man Bart put away for framing Krusty the Clown and trying to murder his aunt Selma. Bob, stewing in anger, is up for parole and ready for revenge. He becomes such a threat that the family is put into witness protection, but Bob follows them to their new houseboat on Terror Lake. Bob executes his plan by cutting the house loose and tying up the family, before finally going to finish off Bart. Bart, in real mortal danger, plays to Bob’s ego and singing voice by getting him to sing the score to the HMS Pinafore. The song buys Bart enough time to ride back into Springfield and get caught by the police (thankfully they drifted by a brothel) where Bob is locked up once again.


Like any great episode of the series, you mix in a great story with great humor, and you hit a home run. First off, lets analyze what’s really happening here – someone is trying to murder Bart. And not just anyone is looking to do the deed, it’s an evil genius who is justified in doing so (in his own mind). Bob isn’t your run-of-the-mill psychopath, he’s cultured and intelligent, which makes him that much more dangerous. It also makes it that much more impressive when he’s stopped by a ten-year-old boy multiple times. Sideshow Bob is one of my favorite characters, especially since he’s voiced by Kelsey Grammar. Almost every Sideshow Bob episode is great, even if his motives get a little loony at times.

But after you get past the chilling story of someone chasing Bart with a butcher knife, you get the jokes. The jokes in this episode are the BEST. This episode still manages to make me laugh hysterically at everything. These include, but are not limited to: the cactus patch, the Germans being evil reference, Bob doing aerobics, why Bart can’t jump off the ship, the elephant parade, the song number, Homer barging in to Bart’s room, and THE RAKE. THE MOTHERLOVING RAKE!!! Seriously, do yourself a favor and watch this episode. It really is one of the best for a reason.

Side-note: the season eight episode where David Hyde Pierce plays his brother Cecil is an honorable mention for this list.


3. Homer at the Bat (Season 3, Episode 17)


I love baseball. I’ve been a huge baseball fan for as long as I can remember. While pro wrestling is my favorite sport, baseball is my favorite “legitimate sport” (are you happy now, wrestling haters? Ugh). And what could be better than nine major league ringers playing their own voices, and being tricked into playing on a company softball team, just so rich Mr. Burns can win a bet?

Homer convinces his power plant coworkers to sign up for the company softball team, when he reveals he has a secret weapon this year. His “magic bat” makes the team have their best season ever, so Burns makes a million dollar bet with rival power plant owner Aristotle Amadopoulos. In order to guarantee victory, Burns recruits nine major league players to work at the power plant, and join the team. They replace all of the regular players, but as the big game approaches, they succumb to a hilarious series of misfortunes. The end result sees the plant regulars take the field, except for right fielder Homer Simpson. However, in order to ensure his victory, Homer is sent in to pitch hit with bases loaded. Homer is hit by the pitch, signaling a walk, and the winner runner walks home. The episode ends with the BEST scene in the series history.

Seriously, what’s better than Homer playing baseball? The major league players are hilarious, and really tie into this episode’s success. They use everyone in a fantastic role, and really hit a home run (ahem). This episode just works.


And now, a countdown of all nine misfortunes!

-Steve Sax is pulled over by the police, and sent to jail after being unable to answer for New York City’s unsolved crimes, facing three consecutive life sentences.
-Mike Scioscia gets radiation poisoning after gleefully enjoying his job at the powerplant, and may not even live through the night.
-Ken Griffey Jr. gets gigantism after overdosing on nerve tonic.
-Jose Canseco assists a lady in recusing her baby and cat from a burning building, but then gets held up removing literally EVERYTHING from her home.
-Wade Boggs is knocked unconscious in a bar fight with Barney over who England’s greatest prime minister was.
-Ozzie Smith visits Springfield’s Mystery Spot, and disappears off the face of the planet.
-Don Mattingly is fired after Mr. Burns tells him to shave his nonexistent sideburns (but he still likes him better than Steinbrenner)
-Roger Clemens is hypnotized into thinking he’s a giant chicken, thanks to Mr. Burns’ attempt to “motivate” his players goes awry.
-Darryl Strawberry, the resident kiss-ass, arrives and plays perfectly, replacing Homer until Burns decides to pitch hit Homer in his place.

Simpsons Softball Team Photo

Genius all the way. And did I mention the closing credits song number is perfect too?


2. Who Shot Mr. Burns? (Part 1: Season 6, Episode 25 – Part 2: Season 7, Episode 1)


To date, this is the only true two-part episode the series has ever done. Not only is it a great mystery story that’s written exceedingly well (they really do a great job making you wonder whodunit) but it was also THE talk of the summer of 1995, with an intense cliffhanger that led to several contests for fans to participate in.

If you want to chastise me for “copping out” and blending two episodes into one position, note that if I had to choose, I would rank Part 1 only and leave Part 2 off the list altogether. If you’re anal like that (some of you are).

Groundskeeper Willie strikes oil underneath Springfield Elementary, and the school becomes insanely wealthy. However, Mr. Burns is outraged that a school could make that kind of money, and forms a plan to drill the oil himself. He ends up outraging everyone in the community in the process. His sabotages the school’s future, and destroys or shuts down almost every local business in town. He also outrages Homer by never remembering his name. His plan reaches full insanity when he decides to block out the sun, making the town entirely reliant on his energy plant. This pushes Smithers, Burns’ closest ally, completely over the edge. When Smithers refuses to fall into line, he’s fired, and becomes a drunken wreck. Everyone attends a town meeting, bearing firearms, to discuss action, but no one has the guts to actually stop Burns when he calls them out. As he skips away, he’s mysteriously shot, and the entire town becomes a suspect.


Following the summer with everyone wondering who could possibly be behind it, the clues fall into line as Chief Wiggum does his job (for once) and they nail Homer for the crime after Smithers mistakenly confesses. Homer confronts Burns, and after he comes to, he explains what really happens – it was just an accident when his gun slipped into Maggie Simpson’s hands. Thus, Maggie shot Mr. Burns.

Part one is perfect. They really establish Burns as an evil old man in this episode. And once the town is calling for his blood, they set up dozens of reasons why people want revenge. Everyone in the family has a good reason to pull the trigger, as do Moe, Barney, Skinner, Willie, Smithers, and of course Tito Puente. The jokes are great, especially with Homer trying to get Burns to remember his name. The scene where Homer gets the thank you letter without his name on it is one of the best. This episode also creates a real dramatic moment between Smithers and Burns, as Smithers proves to be more than just a yes man. Part two isn’t as good, but it still tells a good story as they rule out various suspects in hilarious fashion (especially Moe on the lie detector). They end up identifying Homer due to Burns having brain damage, and those being the only words he can say, after finding an eyelash with Simpsons DNA. Finally, they end with the big reveal, which some saw as a letdown, and others saw as a brilliant twist. It doesn’t bother me. It’s not my favorite, but I don’t have any real problems with it.


Great jokes exist here, but this two-parter excels in storytelling and delivers one of the better cliffhanger endings in television history. The Simpsons were pretty iconic by this point, and the contest to guess who shot Mr. Burns was one of the first to incorporate the internet into prominence. Not only that, but they even ran a special America’s Most Wanted episode to analyze the clues and suspects, to really hit this episode home. In the end, this episode became an incredible journey on the Simpsons roller coaster, and is something they haven’t come close to duplicating throughout their history.


1. Treehouse of Horror III (Season 4, Episode 5)


And now we come to my number one favorite episode of the Simpsons to date. I said in my first part that I did sort of purposely exclude the Halloween episodes, but I couldn’t just force them all out for a good reason. That reason is because the third Halloween installment of the series is my number one favorite episode that they have ever done.

It’s a Halloween party at the Simpsons house, and the party goers share scary stories and play ghastly games. Lisa shares a story about a killer Krusty doll that Homer buys from an occult shop, which tries to murder him but acts lifeless when the family is around. The Twilight Zone inspired short then leads into a King Kong parody, told by the elderly Abe Simpson. Marge plays the role of Ann Darrow as Mr. Burns travels to Ape Island to capture a giant ape (Homer). Homer is put on Broadway, but runs amuck in downtown Springfield, and ends up marrying the girl he fell in love with (is that even legal?). Finally, Bart ends the night with a zombie tale, where he accidentally raises the dead, and the family has to fight them off.

Sound generic? Well, that’s because I REFUSE to spoil this episode for anyone who hasn’t seen it. It’s the best piece of Simpsons storytelling out there. Every single element of this story works. All three shorts have insanely funny highlights and moments, but what seals the deal is that the narrative itself (the Halloween party) is just as funny as the shorts. There isn’t a single joke that fails, and even the ones that don’t get the belly laughs are cut out of syndication anyway, so the episode runs BETTER on TV, believe it or not.

I won’t even say any more. Go watch this episode, and laugh as hard as I did the first time I saw it, and every subsequent time I’ve watched it since.

A-Clown-without-pity king-homer_tv zombies

Dad! You killed the zombie Flanders! (You know what comes next).


Well, there you have it everyone. I’ve just counted down thirty episodes of my favorite television show of all time. It was a lot of fun reliving these memories, but it’s even more fun going back and watching them again! In fact, I’m going to have a marathon of just this list soon. Anyone care to join me?

What is YOUR favorite episode of the Simpsons? Did I include it? Did I leave your favorites out? Let me know in the comments! And please subscribe for more blogs!

Thank you for reading! JERSEY RAIN!


My Top 30 Favorite Episodes of The Simpsons, Part 2 (20-11)

It’s time to continue my countdown of my favorite episodes of the Simpsons! While these are middle pack choices, they are anything but average.




20. Simpsoncalifragilisticexpiala(Annoyed Grunt)cious (Season 8, Episode 13)


There’s nothing quite look a good parody, and it’s even better when it’s a Simpsonized version of a classic Disney film, filled with a brilliant musical score!

Marge’s stress levels are so high, her hair is falling out. To alleviate the issue, the family agrees to hire a nanny. They receive the prim and proper Shari Bobbins (an original character, as she points out) who immediately whips the family into shape through song parodies and helpful advice. Unfortunately, she’s truly powerless to change the family, and they accept who they are.

What makes this episode stand out for me isn’t just how good the parody itself is, but how they incorporate so many classic songs into the episode. Shari sings everything to the kids, including how to cut corners during chores, and even sings the tale of a boozehound (named Barney). Of course, the kids also deliver a song number about their preferences in the nanny, and the finale is all about how the family is happy being exactly how they are (lazy, boorish, and far from perfect). The only thing truly missing was the portrayal of Shari by the original Mary Poppins, Julie Andrews (whom the producers ultimately chose to not use). Still, the episode is funny, clever, and features plenty of spoofing. They even parody several other famous musicals when Shari takes the children to the park. What’s not to love?


My favorite dialog still goes to Shari and Groundskeeper Willie.


19. Home Sweet Homediddly-Dum-Doodily (Season 7, Episode 3)


As much as I love the Simpsons, I generally reject – nah that’s too strong of a word, maybe shy away – from episodes that tinker with Homer being a lousy parent, or Homer and Marge’s marriage being in trouble, etc. Why? Because the show has done a brilliant job of cementing the fact that Homer and Marge are soul mates and that Homer is still a loving and devoted father, even if The Boy bugs him and he can’t truly understand his daughter. However, the third episode of the seventh season tells a much different story, about the kids being taken away when the parents didn’t do anything wrong, and does so in a heartwarming and hilarious fashion.

Through pure happenstance, child services remove Bart, Lisa, and Maggie from their home and send them to live with a foster family. Unfortunately, the foster family are the Flanders, which means the kids are only one house over and completely cut off from their home. Homer and Marge do everything in their power to win back their kids, showing how much they truly do love them, but time is short as Ned prepares to baptize the Simpsons kids, learning that their family has failed to do so. Homer and Marge complete their parenting class just as the Flanders are set to welcome Bart, Lisa, and Maggie into their family through the eyes of God, but Homer saves the day at the last possible moment. The happy family reunites and spills the dirt on the Flanders. Old painty-can Ned.


As I said before, this episode is half heartwarming and half hilarious. The kids are taken away through pure miscommunication, all because Marge didn’t complete her daily chores so Homer could treat her to a spa day for all the hard work and under-appreciation she goes through. The fact that child services jumps to conclusions that are painfully right from their point of view, but painfully wrong from ours, is heartbreaking. They also make sure to tug at the heartstrings while Bart and Lisa discuss all the little things their parents would do for them, while Homer and Marge talk about how much they miss the kids and how they brighten up the house. Homer even tries to play a solo on Lisa’s saxophone, and fails miserably. But there’s the flipside, the jokes are tremendous. The Flanders family is incredibly weird, with their family game nights and Flanders-style nachos. There are plenty of laughs to go around to counter the heaviness of the story.

In conclusion, this episode is a perfect blend of emotions and laughter. It’s definitely one I would recommend.


18. Homer’s Phobia (Season 8, Episode 15)


Hilarity ensues when Homer’s homophobia comes to light, for absolutely no good reason, in this season eight episode that really hits on society’s views of gay people.

The Simpson family befriend a gentleman named John, who’s into cartoons and collectibles and fashion. But after inviting him over to their house, Homer discovers he’s gay (after Marge tells him) and immediately begins to dislike John. Things escalate when Bart starts to act a tad too fruity for Homer’s tastes, so he attempts to straighten Bart out (and of course, fails miserably). The last resort is to take Bart deer hunting, but when the reindeer in a pen revolt, John saves the day, much to Homer’s chagrin, but thanks to his concussion, he’s thankful for the moment.


This episode is a pretty spot-on portrayal of homophobia. Homer doesn’t like the fact that John is gay, because it’s not normal, and because John isn’t extremely stereotypical. That’s exactly how a lot of homophobic people react. They don’t understand something that’s different, so they immediately reject it and mock it. Homer is no exception, especially after he thinks Bart is starting to act queer (a word they stole, according to Homer). But outside the social commentary, is a really funny episode with some classic jokes. All of Bart’s “queer” acts net a laugh, as does every failed attempt by Homer to straighten Bart out. The highlight is the gay steel mill. And of course, the deer hunting failure is the icing on the cake (pink icing, naturally) as an evil robotic Santa saves the day. John Waters portrays the John character perfectly, making him a brilliant one-off character, especially his relationship with Smithers.

When the Simpsons successfully mix social commentary with hilarity, the results are always perfect.


17. I Love Lisa (Season 4, Episode 15)


This is the quintessential Ralph Wiggum episode, so you shouldn’t even have to ask how it made this list.

When Valentine’s Day rolls around, poor Ralph doesn’t receive any cards from his classmates. Lisa writes him one out of sympathy, and he immediately falls for her. The simple-minded Ralph can’t understand that Lisa is rejecting him, and does everything to be with her. He even buys her a Malibu Stacy convertible with tickets to Krusty’s live anniversary special inside. Lisa begrudgingly goes, but when Ralph professes her love for her as Krusty talks to the audience, Lisa breaks his heart on live television. A devastated Ralph channels his emotions into a fantastic portrayal of George Washington that moves his classmates to tears, and Lisa gives him a follow-up card advising they be friends.

Like any good Simpsons episode, this one manages to take a touching story and make it one of the funniest episodes of the series. Season four was a highlight of classic episodes that stick with Simpsons fans for generations, and this is one of the biggest. The dim-witted Ralph is loveable in his naivety, and you really feel for him when Lisa breaks his heart. At the same time, the episode is filled with some of the best Ralph moments in the series, including both of his Valentine’s cards. How many of you out there still quote “I Choo-Choo-Choose You?” The scene where Ralph plays George Washington adds a depth to his character that is sadly forgotten in later episodes. Ralph is a brilliant thespian, even if he’s only doing it under duress. This is a classic Simpsons episode from start to finish.


The Simpsons have done other Valentine’s Day stories, but this one is by far their best.


16. Homer the Smithers (Season 7, Episode 17)


The Simpsons writers always felt that their best stories came from realism and organic elements. No better example can be given than this episode, when Homer takes over the duties of assisting Mr. Burns.

Smithers fails to protect Mr. Burns from a drunken Lenny after a company outing, and beats himself up so badly over it that Burns sends him on vacation. Smithers, fearing that a temporary replacement could outshine him, gives the job to Homer. Homer manages to screw up virtually every single one of Burns’ tasks, from answering his phone to making him breakfast. Burns responds by berating Homer at every opportunity, right in his face, until Homer finally snaps and punches Burns out. Fearing that he’ll get fired (or worse), Homer seeks out an apology, and a terrified Burns sends him away. Now forced to do things for himself, Burns decides that he no longer needs Smithers after all, and fires him. Homer tries to concoct a plan to get Smithers his job back, but when he doesn’t work out, an infuriated Smithers begins to brawl with Homer. The resulting fight pushes Burns right out the window, causing him to sustain injuries that require Smithers’ 24/7 care again. Burns demands that Homer gets what’s coming to him, and Smithers arranges it in the form of a fruit basket.

This episode works from the story and humor standpoint, but as good as the story is, the humor is what makes it stand out. Smithers’ database on how many employees are incompetent sets the tone, and Homer’s various failures keep the laughs rolling. Highlights include Homer delivering Burns his messages, setting corn flakes on fire, and one of my all-time favorite visual gags, when Homer doesn’t know what do to in case of fire. The story arc runs Burns’ personality from an ordering ogre to an impotent infant and back again in record time. It also hints strongly at Smithers’ personal life while he’s on vacation. Many Simpsons episodes have a side-story, but other than Smithers’ trip, this one puts the focus squarely on Homer.


Who would’ve thought Mr. Burns’ mother was still alive?


15. Lisa on Ice (Season 6, Episode 8)


Remember how I said the Simpsons are great at doing touching episodes to deliver the feels, while still delivering the laughter? Well, here is the best example yet.

Principal Skinner creates a system called Academic Alerts, to inform the students when they’re failing a subject. Lisa discovers she’s close to her first F ever, in gym class. The coach agrees not to fail her if she joins an outside sporting program, but she simply has no athletic ability. However, following one of Bart’s hockey games, it’s discovered she has perfect goalie reflexes, and is recruited to be on a rival pee-wee hockey team. Lisa excels, and forces her and Bart to compete over their father’s love, who judges their abilities in sports. The two teams meet for a showdown, and it comes down to Bart taking a penalty shot at Lisa, with a tie game and seconds on the clock. Bart and Lisa have a moment of reflection, and decide to put the rivalry aside. The end result is a tie game, which infuriates the audience as Homer cries that his kids are losers.

This episode solidifies a very important subject that the Simpsons don’t touch on very often – the love that Bart and Lisa share for each other. They’ve done sibling bonding moments before, but this one shows that they care for each other deeper than any competition, and most importantly, their bond as brother and sister is deeper than they would allow a sporting competition to interrupt. Aside from that, and the tear-inducing flashbacks, we get some of the show’s best running gags to date. “Me fail English? That’s un-possible!” That came from this episode. Bart and Lisa’s brawl and the lightswitch interference are gold too, but my favorite joke is Homer and the pie. At the end of the day, this episode will move you, and make your belly hurt from laughter. It’s a perfect story blend.


To be perfectly fair though, gym class was a BS grade. What? Climbing a rope is hard!!!


14. Deep Space Homer (Season 5, Episode 15)


It’s Homer in space. It writes itself!

Homer is selected to be part of the space program, when NASA decides they need to keep their television ratings up against the current crop of entertainment, which includes Married With Children and Home Improvement (feel old now?). They decide to send up the “average man.” Homer is selected after prank calling NASA, but they take Barney too after Homer attempts to shift the blame of his call. Barney excels in training, and is chosen, until his alcoholism gets the best of him. Homer goes up with Buzz Aldrin (voicing himself!) and Race Banyon (who?). Of course, being Homer, something has to go wrong. Homer smuggles potato chips aboard, and when they get loose and he attempts to devour them, he destroys their experimental ant colony. To rid the shuttle of ants and chips, they open up the airlock door, almost losing a the un-strapped Homer in the process. Homer ends up saving the day with an inanimate carbon rod, but the rod steals the spotlight away from him after the safe landing.


Like I said, this episode really does write itself. All you need is a character like Homer in a situation like outer space, and the jokes fly. The potato chip and ant gag is a Simpsons classic, especially when the reporters think that giant space ants have taken over the shuttle. The inanimate carbon rod becomes a star twice in the same episode. The training sessions are hilarious, and the references to Al Bundy and Tim “The Tool Man” Taylor are perfect. My personal favorite joke is Homer singing the Golden Grahams song while they attempt the risky landing. Someone as out-of-shape as Homer would never be allowed into space, but unrealistic scenarios make for golden episodes of cartoons.

Hail ants.


13. Homie the Clown (Season 6, Episode 15)


An old bit of Simpsons trivia is that Krusty the Clown was going to be Homer in disguise. The writers of the show, during the Tracey Ullman days, wanted to establish Krusty as a hero to Bart, and more of a father figure than Homer. Then, when Bart eventually realized the truth, he would respect his father more. This is the reason why Krusty is drawn so similarly to Homer. The storyline was ultimately forgotten about, since the writers didn’t believe Homer could pull off such an elaborate double-life. However, in season six, Homer does become Krusty, and it’s awesome.

Krusty has spent himself into a hole, and there’s only one thing left he hasn’t done – open a clown college to train regional Krustys. He advertises the college on a billboard, which successfully hypnotizes Homer into signing up. Homer becomes an extra Krusty in Springfield, but is miserable with his promotional and kid’s party duties. However, when he realizes he can get free stuff and get out of tickets because people mistake him for the real Krusty, he starts to exploit his new persona, until he grabs the attention of Fat Tony who is after the real Krusty for his debts. Homer is taken to the don, but Krusty saves the day, and he and Homer entertain the mobsters, ultimately saving their lives.


This is another episode that resonated with fans, and became highly quotable. Almost any episode involving Fat Tony hits a homerun, and this is no exception. Homer does what most of us would do in a situation like his, exploit the positives while complaining about the negatives. And of course, we all want speed holes in our car now. The Italian stereotypes are just as great as the story of Homer as Krusty. The episode hits it out of the ballpark in every direction, from the bicycle gag with the Godfather music to the mob having it in for every member of Springfield.

Now, you readers have stood in my way long enough. I’m going to clown college!


12. The Way We Was (Season 2, Episode 12)


Every television show eventually does the flashback episode, establishing an angle used in the present that the fans would be interested in. In this case, we learn the story of how Homer and Marge fell in love at their high school prom. It’s one of the best flashback episodes the series has done, and one of the most touching too.

We go back to 1974, during Marge and Homer’s senior year of high school. Homer is a troublesome student, and he’s given detention for smoking in the boy’s room, along with Barney. Marge also lands in detention on this particular afternoon, for burning a bra during a feminist rally. Marge sits down next to Homer, and he is stuck with love at first sight. He sets out to win Marge’s heart, first by joining the debate team, but soon learns Marge is more interested in Artie Ziff, a much more intelligent and articulate choice than Homer. Homer instead tricks Marge into helping him with French, which she’s an active tutor for, but it’s all a lie to ask her to prom. She;s disgusted by his actions and agrees to go with Artie instead. Homer arrives on prom night, but is shooed away by Marge (and horribly rejected by her sisters). He goes to prom alone, while Marge and Artie and crowned prom king and queen. Artie attempts to get frisky with Marge, but she rejects him, and takes pity on Homer after seeing him walking home alone in the mud. She gives him a ride, and the two end up becoming an item.


Every sitcom has done the “how they met” story. Peter Griffin worked as a towelboy at the country club Lois was a member of. Leonard was looking for apartments, and happened to become roommates with the obnoxious Sheldon Cooper. Everyone has a story, but Homer and Marge’s is the best. It proves that they were made for each other, as early as high school. They also establish the Artie Ziff character here, whose obsession for Marge has never truly left. They also plant the seeds for Patty and Selma’s lifelong hatred of Homer. Despite the Bouvier family’s objections, Marge still falls for Homer, and that makes him the happiest man alive.

Stories like this are why the Simpsons are so great. Unfortunately, as time went on, their flashback stories got stupider, incorporating unnecessary 90’s jokes into one, and trying to come up with a summer camp romance story when they were kids too. But the first time they did it, it was absolutely perfect.


11. El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer) (Season 8, Episode 9)


Did you know that insanity peppers and chili cook-offs can make you find your true soul-mate? Well, in the Simpsons, anything is possible, especially in this brilliant tale from season eight.

Homer goes to the annual chili cook-off, with his trusty spoon (that he carved from a bigger spoon). He rips through everyone’s entries, until he comes face-to-face with Chief Wiggum. Wiggum has a secret weapon: “The Merciless Peppers of Quetzlzacatenango, grown deep in the jungle primeval by the inmates of a Guatemalan insane asylum.” One drop of this pepper is too much for Homer, making him a laughingstock of the festival, until he returns with wax in his mouth. He devours several peppers to everyone’s astonishment and horror, and walks off triumphantly, until the peppers make him go insane. He has a strange vision where he’s trapped in the desert, and a mysterious coyote (voiced brilliantly by Johnny Cash) appears as his spirit guide, telling him to find his soul-mate. When Homer questions whether Marge is actually his soul-mate or not, he goes on a journey around town to fulfill his prophecy, and ends up at the Springfield Lighthouse. He takes out the bulb to cause an approaching ship to crash, but Marge turns up. After a brief exchange, they realize they are true soul-mates, and save the ship from it’s collision. Well, they almost do, until it dumps its precious cargo in the water, hot pants.

This episode works on so many levels. For starters, it’s plain ridiculous! And I mean that in a good way. Homer’s insane journey is hilarious, especially after he comes to and makes as many connections to the dream that he can (hey wait a minute, dogs can’t talk!). Again, it’s a Homer-and-Marge test that they’ve done to death, but this time they take a different approach. They establish how deep Homer and Marge’s bond is, even though they’re so different. Marge may be upset with Homer for drinking (which she judges unfairly this time around) but she still loves him, and they still share a kindred spirit. The guest spot with Johnny Cash is one of the best in the history of the show, especially as a Space Coyote. Why isn’t THAT character in the Tapped Out game yet?? This is an episode that hits all the marks on its jokes, and still manages to tell a good, thoughtful story about Homer and Marge in the process.


They’re number one! In your FACE, Space Coyote!


So there you have it guys and gals, ten more fantastic episodes of the Simpsons! Next week before my Halloween takeover guest writer, we will do the FINAL COUNTDOWN (cue cheesy 80s music) and list off my true top 10 favorite episodes. Did any of your favorites make the cut so far? Do you think your favorite is still to come? Leave some comments, and don’t forget to check out part one, to see where all this insanity began! And no, no insanity peppers were consumed during the writing of this blog.

Next time: Part 3, 10-1!

My Top 30 Favorite Episodes of The Simpsons, Part 1 (30-21)

I’m going to break one of my own rules with this blog. Normally, when I do a countdown based on a television show, I like to wait until the series has concluded, as there is a chance that my favorite episode of all time has yet to air. This is why you won’t see a South Park or Big Bang Theory list, but you will see one for Futurama and Buffy the Vampire Slayer. However, with the Simpsons not airing an episode in years that has made me even consider putting it on the list (with one very lone exception), I feel comfortable executing this list now. Family Guy, you’re in the same boat.

With 522 episodes under their belt, and a new season about to start, The Simpsons has been around forever. And yes, like many people, I wish the series would conclude so we could do a full series reflection. Still, my fandom for the Simpsons runs strong. Other than professional wrestling and Star Wars, there is simply no other fandom out there as intense for me as the Simpsons.

Sure, there are some people who don’t care for the Simpsons. Those people don’t need to wake up tomorrow.

All kidding aside, my love for the Simpsons is stronger than ever. FXX recently aired their “Every Simpsons Ever” marathon, which was one of the greatest marathons of any TV show I’ve ever seen. And as some of you know, I have watched one episode of the series every single day in 2014, starting with season 1’s Christmas special and currently residing in the middle of season 12 (as of this writing). I plan to continue my journey into 2015, but I will abandon the daily aspect of the project and just continue watching at my own pace. This is the first 365-a-day project I’m going to successfully finish, and it was damn fun too.

Of course, this begs the question, out of 522 episodes, which do I consider my favorites? This is no easy task, sorting though “Mr. Plow” and “Skinner’s Sense of Snow” and managing to cut the list from 522 down to even 30. And 30 is what I’m going for, because this is my favorite show, and it’s my blog, so I make the rules, dammit!

Even cutting the list down to 30 was a herculean task, but I’m happy with my final selections, and while the order isn’t always 100% accurate (many, many ties in there) the 30 I’ve picked are by far my favorites, and by far some of the best episodes of the show.

Now keep in mind, I’m basing this solely on the overall episode, rather than individual segments. While “Stupid Sexy Flanders” is one of my all-time favorite Simpsons jokes, the actual episode wasn’t anything special. Same with the classic songs like “Mr. Plow” or “Who Needs the Kwik-E-Mart” or “See My Vest” (although the last one did some close). And yes, don’t be surprised to see a majority of chosen episodes be from single-digit seasons.

This was a hard list. A REALLY hard list. But, I enjoy my final choices, and I hope you do too!

Since 30 is a big number to sort through, we’re going to do this in three parts. So get ready for part 1!




30. Treehouse of Horror (Season 2, Episode 3)


I can’t think of a more perfect way to kick off a list of my favorite Simpsons episodes than with the original Halloween special that started the craze.

Oh, and before we dive in too much, I sort of purposely left off the Halloween specials so they wouldn’t dominate the list…with one very big exception, that you’ll see. Don’t worry, all of them are worthy of consideration, and closer to Halloween I will count down my favorite individual shorts – but some overall episodes have the handicap of having a weaker short to hold the rest down – Treehouse of Horror V, for example, has brilliant stories in “The Shinning” and “Time and Punishment” but falls a little flat with “Nightmare Cafeteria.” Get how that works? Good. Let’s carry one.

Homer is admiring his Halloween candy when he decides to see what Bart and Lisa are up to. Up in Bart’s treehouse, Bart attempts to scare Lisa by telling her scary stories, both of which fail to impress, so she counters with the classic Edger Allen Poe tale of “The Raven.” In what would become the norm for the specials, the episode focuses on three individual tales that allow the writers the creative liberty to do anything they want. Earlier specials were connected with a narrative, in this case, scary stories in the treehouse (which is how the episodes got this title). Other examples would be candy-induced nightmares, a Halloween party, a take on the Twilight Zone’s Night Gallery, etc. Each short is brilliant and stands out as some of the best overall shorts in the library of the Simpsons.

1. Bad Dream House

Starting off with “Bad Dream House,” the family moves into a possessed house that looks suspiciously like the home from “The Amityville Horror.” The demonic voice tries to kick them out with scary tactics like bleeding walls and floating furniture, and by convincing the family members to murder each other. However, the family refuses to give in to the house’s demands, and it chooses to destroy itself rather than deal with the family’s shenanigans. We follow that with “Hungry are the Damned,” which gives us our very first introduction to Kang & Kodos, who would become cultural icons on the show. Spoofing the Twilight Zone’s “To Serve Man,” the family is taken aboard a spacecraft “to paradise” where Lisa suspects that the aliens are planning to eat them. Unfortunately, her suspicions turn out to be wrong, and they are dumped unceremoniously in their backyard, after making Serak the Preparer cry. And of course, “The Raven” is the retelling of the Poe classic, with Homer as the narrator, Marge as the lost Lenore, and Bart portraying the raven itself.


All three shorts are brilliant in their own way. The first story takes liberties from every haunted house story they could, including Poltergeist with the basement tombstones and even the Addams Family. The last story has several references to other Poe stories, including every book the raven drops on Homer’s head being a Poe classic. Kang & Kodos’ introduction is a series highlight, as is James Earl Jones appearing in all three shorts – as the voice of the delivery man, Serak, and the Raven’s narrator (when Homer isn’t actually speaking). And of course, who can forget the real comedy as Homer is scared stiff by the children’s stories, while they go to sleep peacefully.


Not just one of the best Halloween specials, but also one of the best overall episodes of the entire series. Treehouse of Horror is a definite recommendation to any Simpsons fan, especially around Halloween.

Quoth the raven, “eat my shorts.”


29. 24 Minutes (Season 18, Episode 21)


This is your curveball episode, as it’s a later episode that actually managed to make it into this list. But, if you’ve seen this first part of the two part season finale, you’ll understand why.

24 Minutes is a spoof on the popular Fox series “24,” which follows agent Keifer Sutherland’s iconic Jack Bauer character as he attempts to stop terrorism. But what sets the show apart from the rest is that it’s shot in real time. Each episode takes place between a certain time of day, from 8 AM-9 AM, or from 5 PM-6 PM, etc. They run in real time (even through commercials) with the iconic clock telling you what time it is, and each season runs 24 episodes – all 24 hours in a day (have they ever done a daylight savings episode?)

The Simpsons easily spoof this with their general 24 minute runtime, as Lisa takes the role of Mary Lynn Rajskub’s character “Chloe O’Brian” and Bart assumes the role of Jack. Jimbo, Kearny, and Dolph are planning to ruin Springfield Elementary’s annual bake sale with the biggest stink bomb ever created, and it’s up to Principal Skinner’s CTU (Counter Truancy Unit) to stop them. When their first agent, Milhouse, fails and is locked in a dumpster with Homer, they choose Bart for the assignment. As he tracks down the bullies, it’s revealed that Martin is a mole on the inside, helping the bullies achieve their plans. Marge is also racing against time to make a cake in the 24 minutes given, and all of the character’s stories intertwine with the classic 24-style multi-screen angles and ticking clocks. Naturally, the day is saved, and Jack Bauer and Chloe O’Brian make cameos, voiced by their respective actors.


While I’ve never been a fan of 24 itself, I like and respect the show’s format, and anything spoofing it is generally quite entertaining. South Park did a spoof of 24 I absolutely loved too, called “The Snuke” in their 11th season, but it involved much more disgusting subject matter (a bomb in Hilary Clinton’s vagina) so I give this one to the Simpsons. Either way, the spoof is tremendous, and it’s a shining beacon among a sea of bad, lame, and easily forgettable later episodes. To wit, I couldn’t even tell you what seasons episodes after 14 fit in to without looking them up, but I can easily talk about Season 18, episode 21, anytime.


28. Trilogy of Error (Season 12, Episode 18)


Much like 24 Minutes, this episode is a string of multiple stories happening at once, but it takes a different approach. This episode was inspired by the 1999 film “Go” as well as “Run Lola Run.” It chronicles the events of one particular day, but from three different points of view: Homer’s, Lisa’s, and Bart’s, intertwining the events into one conclusion at the end of the episode.

Homer’s thumb is accidently cut off, and as Marge races to get him to the hospital, Bart and Milhouse stumble upon the mafia’s illegal fireworks stash. Meanwhile, poor Lisa ends up at another school, and her science project (Linguo, a grammar correcting robot) is destroyed, after she meets a boy like her named Thelonious (voiced by Frankie Muniz). Everything ties into one another, from the police tracking down the mafia, to various car thefts, to how Linguo blows up, and even to how Homer’s thumb is reattached. And to remind everyone it’s the same day, each individual story begins with the garbage men accidently taking out the Flanders’ mailbox.


This is a great episode for both brilliant writing and pop culture homages. Many different films and shows have toyed with the idea of showing one event from several points of view, and the Simpsons hit a home run with their take. While some of the bits are a little silly, like how Homer can lose his thumb and still be functioning normally (normal for him anyway), they do a good job tying all the stories together and wrapping it up with one happy ending. If a later season episode is to be watched, this should definitely be one of them.

Wait, damn, 12 is hardly a later season anymore. Wow.


27. 22 Short Films About Springfield (Season 7, Episode 21)


What if an episode of the Simpsons didn’t have a story at all? What if they spent the 22 minutes simply showing the residents living their lives, and connecting them through brilliantly written segues? You’d get one of the most popular episodes of the series to date!

Now granted, I put it low on my list, but it’s still in the top 30 of 522, so relax.

Bart and Milhouse are being jerks, spraying ketchup and mustard on passing cars from a bridge, when Bart wonders allowed how many stories go on throughout the town. His wonderment is answered as the characters go about their daily lives. Homer accidently traps Maggie in a newspaper dispenser, while Smithers has a severe allergic reaction to a bee sting. Dr. Nick helps treat Grampa who is losing his mind, while Moe avoids a robbery from Snake. But Snake is nearly taken out by Chief Wiggum, who has donuts after a heated debate over McDonald’s Vs. Krusty Burger. Lisa is trying to get gum out of her hair, while Milhouse just wants to use the restroom, and he actually saves a recently kidnapped Snake & Wiggum from Herman, although he does so by accident. And of course, the episode concludes when Nelson makes fun of a very tall man crammed into a tiny Volkswagen Beetle, causing the man to force him down the street with his pants down, as Bart realizes everyone has a story to tell.

We really get time with a slew of characters in this one, including the casual home life of Bumblebee Man, and that Reverend Lovejoy likes making his dog use the Flanders’ lawn as a rest stop. Everyone gets a quick moment to shine (except for Professor Frink), and some of the characters even get theme music, like Cletus and Superintendent Chalmers (who delivers one of the best lines in the show’s history in this one – it’s about the aurora borealis, look it up). It may sound like a cluster, but it’s very intelligently written, and has some classic lines and jokes mixed in.


In college, a friend of mine said this was the last truly great episode of the series, and to some degree he’s right. While there are good episodes that follow, the Simpsons’ official downfall from quality writing started shortly after this episode aired, and took a major fall only a few seasons later. But when it comes to 22 Films About Springfield, you really can’t go wrong with quality.


26. The Mansion Family (Season 11, Episode 12)


Kent Brockman and Britney Spears (voicing herself) host Springfield’s annual pride awards ceremony. They deliver an award to Springfield’s oldest resident, Cornelius Chapman, who dies after Britney plants a kiss on his cheek. Thus, the award goes to the 104-year-old Mr. Burns instead. Realizing he’s not a young man anymore, Burns decides to go to the Mayo Clinic, and leaves the Simpsons in charge of his mansion. Homer decides to live it up like a billionaire, and throws a party on Burns’ yacht. Unfortunately, he can’t sell alcohol until after 2 PM, since it’s Sunday, so they sail out to international waters, where the yacht is seized by pirates. Burns returns home to no yacht, but also under the impression that he’s indestructible due to his having every disease known to man (and some new ones discovered in him only) but in perfect balance.

A good comedy of errors type episode, we get an inside look into Burns’ mansion lifestyle viewed from the eyes of the lower class. Homer, like every one of us, dreams of living the filthy rich lifestyle, and like most of us would, exploits his temporary home to the fullest. I also love the obvious jabs at what we, the lower-to-middle class of society, view as “rich” lifestyle. Everything from too many forks at dinner to safes behind paintings, and even ridiculous concepts like burning and delivering a new bed in lieu of actually making the bed, appear as common for the rich folk. Marge and Lisa even clean a weird laboratory, full of tiny Burns embryos (and one for Smithers), leading to more questions about Burns’ life. The true highlight though, is Burns at the clinic, receiving his diagnosis and interpreting it his own way. And of course, what his social security number actually is.


This episode works well telling both stories, and while the pirate siege isn’t the best joke they’ve ever done, they lead-up to the yacht party is gold. The final touch is Homer crying through the credits, as all the names that scroll by are richer than him.


25. A Star is Burns (Season 6, Episode 18)


This is also the crossover episode with The Critic, featuring the Jay Sherman character from the ABC cartoon (voiced by Jon Lovitz), only yellow like the Simpsons regulars. While some crossover episodes can be letdowns, this one delivers, as Sherman’s character meshes well in the Simpsons universe, but the film festival backstory is the real highlight.

In order to increase the town’s cultural image, Marge proposes they host a film festival. She decides to invite Jay Sherman to be the guest film critic, who accepts the invitation after being threatened by Rainier Wolfcastle over his criticism of Wolfcastle’s McBain franchise. Sherman stays with the Simpsons, and after beating Homer in belching and knowledge of commercial jingles, Homer becomes part of the film jury. The audience is moved by Barney’s black & white film noir depicting his alcoholism, while Homer laughs himself silly at Hans Moleman getting hit in the groin with a football. Meanwhile, Mr. Burns commissions a movie of pure egotism (and blatant Hollywood ripoffs) that the audience rejects, although two of the judges are bribed into voting for it. Homer ends up convinced to vote for Barney’s film, making Marge happy she elected to put him on the panel after all.


While some fans may scoff at the crossover appeal, they end up missing out on a classic episode, full of really great gags. These include Homer’s failure to write Jay Sherman’s name on a sign, the plane from New York, the beer nuts can, the auditions for Mr. Burns, and the classic “boo-urns” joke you’ve probably heard me make a hundred times. I also really love Bart’s reaction to “The Flintstones Meet The Jetsons” and how he blows off Jay’s invitation for the family to visit his show. Another great gag is Wolfcastle staring at his shoelaces. If you’re turned off by the Critic crossover, you’re actually doing yourself a disservice and missing out on a great episode. Give this one another watch.


24. And Maggie Makes Three (Season 6, Episode 13)


As funny as the Simpsons could be, they also had the ability to tell really heartwarming stories too. This is one of their best.

Thumbing through old family albums, Lisa notices that there are no pictures of Maggie anywhere. In response, Homer tells the story of how Maggie came into their lives. Although the Simpsons have done their fair share of flashback – and flash-forward – episodes, this time they merely tell a story that the kids were unfamiliar with. The episode doesn’t rely heavily on time period jokes or futuristic what-ifs, but about the love Homer has for his youngest child. Before Maggie was born, Homer was able to quit his job at the power plant and work at a bowling alley instead, after successfully pulling out of all of his debt. Unfortunately, a celebratory romantic night with Marge leads to her getting pregnant. Knowing how happy Homer is, and how perfect he sees his life, Marge attempts to keep the secret until Patty and Selma spread the rumor around town. Homer is forced back to work for Mr. Burns, who chooses to destroy his spirit by hanging up a plaque that reads “Don’t Forget: You’re Here Forever.” Despite Homer’s misery, it’s love at first sight when little Maggie grasps his finger to say hello. However, the kids are still confused as to why there are no pictures, but Homer has an easy answer: he keeps them in the place where he needs the most cheering up: around his workstation. And as a final touch, he makes sure they cover up the plaque just right so it reads “Do It For Her.”

If I did a top 10 on the most touching moments in Simpsons history, this would undoubtedly be on here, if not the list topper. The entire episode is full of funny gags, but it’s also an emotional tale that shows Homer’s life finally achieving perfection and then falling apart, and it really showcases how horrible Marge’s sisters can be when they want to. It makes you really feel for Homer and connect with him, in ways many previous episodes never did. This episode humanizes Homer, and really gives you a deep understanding for the love he has for his kids. As much of a bumbling idiot Homer can be, he loves his children unconditionally (yes, even the boy) and this really shows you how. It’s a touching episode, and shows that love conquers all, and in a different light too.


That final scene chokes me up to this day. Don’t even care if you judge.


23. The City of New York Vs. Homer Simpson (Season 9, Episode 1)


The season 9 opener brings the Simpsons to New York City, the closest city I affiliate myself with, being from North Jersey. So while this episode has always been a personal favorite of mine for that reason, it’s also a really good episode in general. The World Trade Center plays a big role in this episode, but it still runs in syndication, as the Twin Towers did exist at one point. This is something I’m happy about, not just because I like the episode, but because I feel like we shouldn’t remove media regarding the Twin Towers because eventually it’s like saying they didn’t exist. But hey, we’re not here to discuss that, we’re here to talk about Homer Simpson and his struggles with NYC.

Moe initiates a designated driver program, and the unlucky first driver is Barney. He winds up disappearing with Homer’s car for months, and when they finally track it down, it turns out it’s illegally parked in New York City. Homer and the family go to retrieve it, but Homer is reluctant because he had one bad experience in the city when he was younger. The family enjoys themselves, as Marge and Lisa attend a Broadway musical, while Bart tours MAD Magazine. Meanwhile, Homer attempts to get his car back, and fails miserably, between the boot on the car and his needing to pee after downing too many crab juices. Desperate to escape New York, he damages his car and infuriates the locals before retrieving his family and driving away unhappy.


Naturally, the number of New York related jokes is a highlight, but the episode also focuses on telling both the good and the bad side of the city. Homer experiences most of the bad, while his family gets to see the good. Homer needing to pee and the bathrooms on the observation deck is a funny gag, as is the “I’m Checkin’ In” song used in the play about the Betty Ford Clinic. Everything that happens to Homer with his car is one big highlight, especially how he frees the car and exits NYC. As with many episodes, it’s one you have to watch to really appreciate, and I can’t really explain the significance of the jokes involved by typing alone.

Also, for those of you into Simpsons trivia, this episode marks the very first appearance of Duffman. OH YEAH!



22. Lisa’s Wedding (Season 6, Episode 19)


This is the first “what-if” Simpsons futuristic episode and a damn good one too. It takes place in the distant year of 2010 (entertaining for specific jokes) and also features the voice talent of Mandy Patinkin (Inigo Montoya!) as Hugh Parkfield, Lisa’s first love. The Simpsons have done other futuristic episodes, and even managed to string together a coherent storyline for some of their later stories (including Bart’s girlfriend Jenda) but this first time was the best, and honestly, the most realistic one to date.

Lisa meets a mysterious fortune teller, who looks deep into her future, and shows her falling in love with a British student at university. Lisa’s happiness and their relationship is tested when he comes home to meet her parents, and get involved with their family traditions. While Lisa is a top student, Bart is a construction worker, and Homer is still at the same position he’s always been at the plant, as his supervisor is Milhouse and Lenny & Carl are in charge. The best part is that Maggie, although she’s a teenager, still doesn’t talk as the writers find ways around this. Hugh winds up mortified over marrying into Lisa’s family, and acts like they won’t see them after the marriage. He can’t comprehend that Lisa still wants to see them even though she always complains about them. Lisa winds up calling off the wedding, because even though her family may annoy her, she still loves them. The present day Lisa develops a better understanding of her father, and gives him a big hug to show him how much she cares about him.


This episode works because it’s a very real take on what could happen in the future. Bart obviously isn’t likely for college, so he’s working a labor job, and living at home while frequenting bars and strip clubs. Of course Homer isn’t going anywhere at his job, that much has always been clear. Maggie becoming a punk is pretty funny, especially how they get around her talking. Mr. Burns is cryogenically frozen, Martin Prince is thought to have perished in a science lab accident, and it turns out Milhouse and Lisa DID have a thing…but Milhouse doesn’t count. A lot of really good gags to hype up the potential future, and a very touching moment with Lisa honoring her family to make this a great overall episode.

Too bad Homer liked Octopussy, that was my least favorite Bond film.


21. Lisa’s First Word (Season 4, Episode 10)


The second best flashback episode the Simpsons have ever done (spoilers: the best is coming down the list) tells the story of Lisa’s first word, as well as how Bart took to the news that would be a big brother.

Dealing with Bart in the terrible twos was bad enough, but when Homer learns Marge is pregnant, he needs to find them a bigger place to live. They wind up at 742 Evergreen Terrace, thanks to Homer’s father selling their family home. We also get to see where Bart’s love for Krusty the Klown began, during his Krusty Burger giveaway at the 1984 Olympics. Unfortunately, Bart’s love for clowns leads to Homer building a horrifying bed for Bart when his crib is given to Lisa. Bart attempts to rid the house of his new sister, upset that she’s now the center of attention, until Lisa utters her first word: Bart. Bart immediately falls in love with his sister, beginning the bond they share that the show has done a really good job promoting over the years.

As good of an episode that this is with the humor, it’s also another very heartwarming story that really shows how Bart and Lisa’s relationship began. It also shows a lot of firsts, like Bart placing Krusty as a hero, Homer borrowing stuff from Flanders only to never return it, and of course, how Grampa ended up in a home. Most importantly, it also reveals Maggie’s first word, although nobody is around to hear it. She says “daddy” after it’s revealed that Bart refused to say the word as a child, and Lisa also referred to her father as Homer when she started to talk. An excellent episode, and one of the best touching episodes the show has ever done.

Can’t sleep…clown will eat me…



Well guys, that wraps up part one of my list. Still twenty episodes to go! Any surprises here? Any episodes you think may make the cut? I’d love to hear your thoughts in the comments, and stay tuned for part two, as we count down the middle of the pack, leading all the way up to my number one favorite episode of the Simpsons.

I was saying boo-urns…