As The Simpsons turns 30, a superfan picks the best 20 episodes ever

Commentary: For the 30th anniversary of The Simpsons, a look back at the funniest, quirkiest and weirdest episodes.

Bonnie Burton
Journalist Bonnie Burton writes about movies, TV shows, comics, science and robots. She is the author of the books Live or Die: Survival Hacks, Wizarding World: Movie Magic Amazing Artifacts, The Star Wars Craft Book, Girls Against Girls, Draw Star Wars, Planets in Peril and more! E-mail Bonnie.
Bonnie Burton
12 min read

Which character is your favorite in 30 years of The Simpsons?


I've been a fan of The Simpsons since it first aired on Fox on Dec. 17, 1989. I loved seeing an animated series that celebrated a family that was anything but perfect. 

Homer Simpson is a (sometimes lovable) buffoon, while Marge Simpson, his wife, is a little too accepting of Homer's flaws. Bart is the ultimate prankster, Lisa is a know-it-all and Maggie is a baby who mimes her words. In the '90s, the Simpsons became my all-time favorite family to watch every week. 

To celebrate the 30th anniversary of The Simpsons, I took a look back at some of the best episodes of the animated series' impressive run. Got any to add? Share them in the comments. 

1. I Love Lisa (season 4)


Lisa yells on TV that she's not dating Ralph in the episode "I Love Lisa."


Lisa gives Ralph Wiggum a Valentine's Day card out of pity, and he falls hopelessly in love with her. Lisa doesn't feel the same way, but she takes advantage of his affection to be his date to see Krusty the Clown's anniversary special. But when Ralph says on live TV that he loves Lisa and wants to marry her, Lisa loses her patience and shouts at Ralph that she never liked him, breaking his heart. Lisa makes it up to Ralph during a President's Day pageant, and they end up friends again.

Best quote: "You Choo-Choo-Choose me?" -- Ralph Wiggum

2. Homer's Phobia (season 8)


Director John Waters guest stars on The Simpsons.


When Marge tries to sell her grandmother's priceless Civil War doll (which turns out to be a whiskey bottle) at a store called Cockamamie's, she befriends gay store clerk John (voiced by indie director John Waters). Marge invites John over for dinner, and Homer ends up liking him. Homer later freaks out when he finds out John is gay. Marge ignores Homer's sudden homophobia, and continues to spend time with John, as do the kids. 

When Homer notices Bart is showing unusual tendencies such as choosing cupcakes with pink icing over chocolate icing and wearing a wig while dancing to records, he gets nervous and decides to "fix" Bart from becoming gay. What ensues is a ridiculous but hilarious attempt to make Bart more manly by taking the boy to visit Ajax Steel Mill, which is full of manly men working. Little does Homer know the mill is full of gay steel workers who transform the mill into a gay nightclub during breaks. 

It's an interesting take on the irrationality of homophobia, especially considering few primetime TV shows were approaching the issue of homosexuality and homophobia at the time. 

Best quote: "You know me, Marge. I like my beer cold, my TV loud, and my homosexuals FA-LAMING!" -- Homer Simpson

3. Homer's Enemy (season 8)


Frank Grimes sees Homer's incompetence at the nuclear power plant firsthand. 


Homer's been fired from the Springfield Nuclear Power Plant multiple times and always gets his job back. In this episode, a new employee at the power plant named Frank Grimes is slowly driven crazy trying to figure out why Homer's incompetence goes unnoticed by anyone besides him. The episode is a great reminder of how Homer never seems to fail, even though he probably would in the real world. But it's also a good reminder to not let your jealousy over a co-worker's undeserved success ruin you in the end. 

Best quote: "I have had to work hard every day of my life and what do I have to show for it? This briefcase and this haircut!" -- Frank Grimes

4. A Star is Burns (season 6)

Springfield puts on a film festival to attract more tourists, and Mr. Burns spends millions trying to get a film made about his life. New York City movie critic Jay Sherman (voiced by Jon Lovitz) is invited to critique the films made by Springfield's amateur filmmakers. The films include Apu's Bright Lights, Beef Jerky (Kwik-E-Mart security footage), Moe's musical number Moe Better Booze (a commercial for Moe's Tavern), Bart's The Eternal Struggle (home video footage of Homer attempting to squeeze into a pair of tight pants), Ned Flanders' film about Moses, Hans Moleman's Man Getting Hit by Football (footage of Moleman getting hit in the groin by a football) and Barney's introspective film about alcoholism called Pukahontas.   

Best quote: "Listen, Spielbergo, Schindler and I are like peas in a pod: We're both factory owners, we both made shells for the Nazis, but mine worked, dammit! Now go out there and win me that festival!" -- Mr. Burns

5. One Fish, Two Fish, Blowfish, Blue Fish (season 2)


A sushi chef prepares the poisonous fugu fish on The Simpsons. 


Homer eats the trendy but poisonous fugu fish at a Japanese restaurant and thinks he's dying. The doctor gives Homer only 22 hours to live, so he decides to do everything on his bucket list. Items include having a father-son talk with Bart, listening to Lisa play saxophone and making a video for Maggie to watch when she's older. It's one of the more sentimental episodes, but spoiler alert -- Homer doesn't die. 

Best quote: "I am alive! From now on, I vow to live life to the fullest!" -- Homer Simpson. (Next scene shows Homer sitting on the couch watching bowling tournaments while eating a bag of pork rinds.)

6. Itchy and Scratchy Land (season 6)


Rogue robots attack the Simpsons at Itchy and Scratchy Land.

Video screenshot by Bonnie Burton/CNET

When the Simpsons go on a vacation to the newly opened Itchy and Scratchy Land theme park, not all is as it seems. Unlike Disneyland's motto of "The Happiest Place on Earth," the motto to Itchy and Scratchy Land is "The Violentest Place on Earth" -- for good reason. As the family enjoys the park all to themselves, animatronic robot characters break free and attack the family. 

Best quote:  "This truly was the best vacation ever. Now let us never speak of it again." -- Marge Simpson

7. Cape Feare (season 5)

The Simpsons are forced to enter witness protection and move to Terror Lake after Sideshow Bob (voiced by Kelsey Grammer) threatens to kill Bart. Previously, Bart convinced the police to put Sideshow Bob in jail for attempting to frame Krusty the Clown for armed robbery. Sideshow Bob was put in jail again for attempting to kill Selma on their honeymoon. (Clearly, Sideshow Bob isn't one to let the law get in his way). But what makes this episode extra fun to watch are all the references to the movie Cape Fear about a paroled criminal who harasses the lawyer who put him in jail. 

Best quote: "Bart Simpson? That spirited little scamp who twice foiled my evil schemes and sent me to this dank, urine soaked hellhole." -- Sideshow Bob

8. The Itchy and Scratchy and Poochie Show (season 8)

This episode is a great commentary on how meddling network executives can ruin a show by trying to "fix" it. The cartoon within The Simpsons, Itchy and Scratchy, gets a new character named Poochie. But Poochie proves to be unpopular with fans and the cartoon's ratings plummet. Eventually, Poochie is written out of Itchy and Scratchy and the show returns to normal. Apparently, The Simpsons writers created the episode in response to a real-life Fox executive who suggested the show add a new main character to liven up the series. This just goes to show that if you insult a Simpsons writer, your bad idea will end up being mocked in a future episode. 

Best quote: "We at the network want a dog with attitude. He's edgy, he's 'in your face.'  You've heard the expression, 'Let's get busy?' Well, this is a dog who gets 'biz-zay!'" -- TV network exec

9. Homer the Great (season 6)

Homer stumbles on a Freemasons-esque secret society operating in Springfield and joins. Now he gets to indulge in the order's perks, like an underground byway that avoids Springfield's traffic jams. Homer ends up becoming the "Chosen One" when the members discover a birthmark in the shape of the Stonecutters' emblem right above his butt.

Homer tries to use his new power to better the community. But the Stonecutters get annoyed after Homer tries to make too many changes and start a new secret society excluding Homer aptly called The Ancient Mystic Society of No Homers. 

Highlights include Star Trek actor Patrick Stewart voicing Number One, the original leader of The Sacred Order of the Stonecutters. Also Homer replaces all former Stonecutter members with monkeys he trains to reenact Civil War battles.

Best quote: "You have joined the Sacred Order of the Stonecutters who since ancient times have split the rocks of ignorance that obscure the light of knowledge and truth. Now let's all get drunk and play Ping-Pong!" -- Number One

10. Mom and Pop Art (season 10)


Homer ruins a BBQ pit and makes art by accident. 


Homer tries and fails to build a barbecue pit and hits it with an iron bar over and over out of frustration. It ends up being discovered by a modern art dealer who mistakes the bashed-up barbecue for artwork. The episode is an interesting commentary on the absurdity of the art world and how fickle collectors can be. During the episode, Homer tries to find inspiration to make the ultimate piece of art, but floods Springfield in the process. Cut to Milhouse sporting a pair of ugly high-water pants, delivering one of the most quotable lines in Simpsons history.

Best quote: "My feet are soaked, but my cuffs are bone dry! Everything's coming up Milhouse!" -- Milhouse 

11. Bart on the Road (season 7)


Martin, Milhouse, Bart and Nelson wear wigs they bought during their road trip.

Video screenshot by Bonnie Burton/CNET

Bart makes his own driver's license, gets a rental car and road-trips with friends Milhouse, Martin and Nelson to Tennessee to visit the World's Fair. They are off by 14 years and end up stranded, while wearing wigs. 

Best quote: "We're not going to a grammar rodeo. That was just an alibi, Milton." -- Bart Simpson

12. Deep Space Homer (season 5)

Homer Simpson and Barney Gumble compete with one another to become NASA astronauts. Homer smuggles potato chips on board the shuttle, and when the floating chips threaten to clog the controls he swims through the air eating the chips as fast as possible. It's like Apollo 13 with chips! Homer also accidentally flies into an ant farm on board, destroying it and letting the ants and chips loose in the shuttle, which leads the local news to believe alien ants are headed to Earth. In the end, Homer saves the day and impresses real-life astronaut Buzz Aldrin

Best quote: "The Corvair spacecraft has apparently been taken over, 'conquered' if you will, by a master race of giant space ants. It's difficult to tell from this vantage point whether they will consume the captive Earthmen or merely enslave them. But, one thing is for certain: There is no stopping them; the ants will soon be here. And I, for one, welcome our new insect overlords." -- TV anchorman Kent Brockman

13. You Only Move Twice (season 8)

Homer and family move out of Springfield to Cypress Creek after he's offered a cushy job at a new company run by a super villain named Hank Scorpio. Of course, Homer is clueless to Scorpio as a stereotype James Bond villain, and thinks he's the best boss he's ever had. 

Best quote: "Homer, on your way out, if you wanna kill somebody, that would help me a lot." - Hank Scorpio

14. Rosebud (season 5)


Lisa Simpson hugs Mr. Burns' childhood teddy bear named Bobo

Video screenshot by Bonnie Burton/CNET

Springfield's millionaire resident Mr. Burns seems like he has everything money can buy, but he's missing his childhood teddy bear Bobo. The bear is now owned by Maggie Simpson, and Burns will do anything to get his hands on it. Burns threatens to cut off all TV and beer from Springfield if Maggie doesn't give him Bobo. Riots ensue, but the angry townspeople can't say no to Maggie, who doesn't want to give up her beloved toy. Eventually, she feels sorry for Burns and gives him back his Bobo. One of the more notable moments in this episode is a random performance by The Ramones who play at Burns' birthday party.

Best quote: "Look at all the wonderful things you have, Mr. Burns. King Arthur's Excalibur, the only existing nude photo of Mark Twain and that rare first draft of the Constitution with the word 'suckers' in it." -- Smithers

15.  El Viaje Misterioso de Nuestro Jomer (season 8)


Homer Simpson eats an extremely hot pepper and goes on a spiritual journey. 

Video screenshot by Bonnie Burton/CNET

The episode is Spanish for "The Mysterious Voyage of Homer." During a chili cook-off, Homer eats an exotic hot pepper that causes him to spend the rest of the night hallucinating in the desert. He has an epiphany that Marge might not be his real soulmate. The visuals during Homer's hallucination sequences are both beautiful and trippy. The episode is also extra cool because country singing legend Johnny Cash is the voice of the coyote that guides Homer on his journey. Luckily in the end, Homer figures out Marge actually is perfect for him.

Best quote: "Maaaaaarrge! We're missing the chili! Less artsy, more fartsy!" -- Homer Simpson

16. Simpsons Roasting on an Open Fire (season 1)


The first episode of The Simpsons explains how they got their family dog.

Video screenshot by Bonnie Burton/CNET

This episode introduced the world to the dysfunctional-yet-loving Simpsons family. It's also a touching look at how to have a wonderful holiday even when everything goes wrong. Mr. Burns cuts the employee holiday bonus. Marge has to spend all the money for presents to get a tattoo removed from Bart's arm. So Homer works another job as a mall Santa. He also ends up losing his earnings at the racetrack, but in the end, they leave the track with the losing greyhound dog, who becomes the family pet Santa's Little Helper.

Best quote: "If TV has taught me anything, it's that miracles always happen to poor kids at Christmas. It happened to Tiny Tim, it happened to Charlie Brown, it happened to the Smurfs, and it's going to happen to us!" -- Bart Simpson

17. Girly Edition (season 9)

Bart and Lisa compete for best news anchor on a children's educational news program. But the real gem is when Homer exploits Grampa Simpson's elderly status to get a helper monkey named Mojo, which he quickly trains to loot doughnut shops. While Bart and Lisa learn a valuable lesson about sibling rivalry, Homer figures out the hard way that he's a bad influence on the monkey, who becomes just as addicted to beer and unhealthy snacks as he is.

Best quote: "Pray for Mojo." -- helper monkey

18. Treehouse of Horror (season 2)


Aliens Kang and Kodos are fan favorites in multiple Treehouse of Horror episodes from The Simpsons. 


It's hard to pick the best Treehouse of Horror episode of The Simpsons, but as far as horror parodies go, the first Halloween episode is one of the most entertaining. The first segment involves a haunted house based on horror classics The Amityville Horror and Poltergeist. In the second segment, tentacled aliens Kang and Kodos abduct the Simpsons. The third segment is an adaptation of Edgar Allan Poe's poem The Raven with Homer being tormented by a raven that looks a lot like Bart. 

Best quote: "Anyone from a species that has mastered intergalactic travel, raise your hand." -- Kodos

19. Marge vs. The Monorail (season 4)

When Springfield wins $3 million in a lawsuit against Mr. Burns for illegal dumping of nuclear waste, the town decides to spend it on a monorail headed up by a smooth-talking stranger named Lyle Lanley. Even though Lanley wins over the town with his charm, Marge and Lisa think he's a con man. Meanwhile, Homer decides he should train to be the monorail's conductor. As expected, the finished monorail is a nightmare and becomes a death trap. Homer heroically uses Lard Lad's giant doughnut sign as an anchor to stop the train. Notable moments include Leonard Nimoy playing himself at the monorail's launch party, and no one recognizing him. The episode is also a spoof on the 1962 film The Music Man, with The Monorail Song resembling the Music Man's Ya Got Trouble.

Best quote: "Doughnuts. Is there anything they can't do?" -- Homer Simpson

20. Who Shot Mr. Burns? Part 1 (season 6)
Who Shot Mr. Burns? Part 2 (season 7)

Mr. Burns blocks out the sun so he can make more money from everyone who now has to use more electricity. But he's stopped suddenly by a mystery person who shoots him outside Springfield's town hall. Who did it? Since the story is shot as a two-parter, it's a cliffhanger. Everyone is a suspect, which is not surprising since Mr. Burns has pretty much made an enemy out of everyone in Springfield. 

In part 2, Smithers thinks he accidentally shot Burns while drunk. He's arrested but let go. Lisa decides to tackle the case herself, eliminating suspects one by one. There's even a fun Twin Peaks reference when Chief Wiggum dreams of a red-curtained room with Lisa talking backwards, telling him to check Burns' suit for more clues.

In the end, it's discovered that baby Maggie shot Mr. Burns after he tried to take away her candy. It's determined that the shooting was an accident… or was it? 

Best quote: "Well sir, you have certainly vanquished your enemies. The elementary school, the local tavern, the old age home. You must be very proud." -- Smithers 

Originally published Dec. 16