Entertainment TV & Film 20 Most Iconic Episodes of 'The Simpsons' Share PINTEREST Email Print TV & Film TV Shows Comedies Dramas Documentaries Shows For Kids Movies By Nancy Basile Nancy Basile is an entertainment writer who specializes in cartoons, comic books, and other elements of pop culture. She has more than two decades of experience writing. our editorial process Nancy Basile Updated May 12, 2019 "The Simpsons," a long-running animated television show, debuted in late 1989 and has no sign of pending cancellation. 01 of 21 Decades of Clever Wit and Incisive Insight FOX The iconic show has attracted millions of fans and even praise from critics. But choosing the 20 best episodes of "The Simpsons" is difficult. Whether the episodes focus on the gluttonous eating habits of Homer Simpson, the show's anti-paterfamilias; Bart, the ever-mischievous son and most popular character; Marge, the steady and sensible wife; Lisa, the genius but ever-exasperated younger sister; or Maggie, the adorable baby girl, it's difficult to limit this list to under two dozen. But, after careful consideration—and decades of watching—here are the most iconic episodes of one of television's the longest-running shows. 02 of 21 "Bart the Daredevil" FOX Bart is quite the prankster, so you might think that the No. 1 episode would focus on one of his many practical jokes, but it is his devil-may-care attitude that underpinned the very best half-hour segment. In "Bart the Daredevil," first aired on Dec. 6, 1990, Bart embarks on a life of death-defying feats when he sees a daredevil perform at a monster truck rally. This episode makes the list mainly because of Homer's long, painful fall down a cliff—twice. "Bart the Daredevil," like other early episodes, isn't as much about Homer being a doofus, as it is about a father who's trying his best, fails and then redeems himself. 03 of 21 "Burns Verkaufen der Kraftwerk" FOX In "Burns Verkaufen der Kraftwerk," ("Burns Selling That Power Station"), which first aired on Dec. 5. 1991, Mr. Burns, the imperious boss at the Springfield nuclear plant where Homer works, sells the plant to a group of Germans. While the episode provides some great humor depicting workers either sucking up to or alienating their new bosses, the best part has nothing to do with the corporate takeover or job losses; it's Homer in the Land of Chocolate. Homer imagines a Land of Chocolate, in which he prances, even eating a passing dog. He gets excited about a 50-percent off sale, although the chocolate is all free. Who wouldn't love the Land of Chocolate? 04 of 21 "Cape Feare" Twentieth Century Fox In "Cape Feare," the Simpsons family enters the FBI's witness relocation program to escape Sideshow Bob when he is paroled from prison. But Sideshow Bob—played by perennial guest star Kelsey Grammar, whose sonorous voice adds heft to the role—is determined to get to Bart and follows the family, which leads to a final showdown on a houseboat. Bart is only saved when his last request before dying is to hear Sideshow Bob sing the entire score to "H.M.S. Pinafore." Sideshow Bob replies with his usual wit, "Very well, Bart. I shall send you to heaven before I send you to hell." In the end, "Bob's vanity foils him yet again," notes IMDb. 05 of 21 "Duffless" Pricegrabber.com In another top episode, alcohol is the punchline. In "Duffless," which first aired on Feb. 18, 1993, Marge asks Homer to give up beer for a month after he's arrested while driving drunk. During the episode, Homer attends AA-type meetings and rides Lisa's bike after his driver's license is revoked. The subplot involves Lisa using Bart as a hamster for her science experiment, highlighting the rivalry between the siblings. This is a well-rounded, hysterical episode, ending with Homer choosing Marge over his favorite—and fictional—Duff beer. 06 of 21 "A Fish Called Selma" FOX "A Fish Called Selma," which first aired on March 24, 1996, showcased the considerable talent of the late Phil Hartman as Troy McClure. McClure's agent, played by Jeff Goldblum, encourages McClure to be seen in public with a woman in order to boost his career. (There are rumors he does strange things with fish!) Troy starts dating Selma—one of Marge's older sisters—and it pays off. Eventually, they marry, but Selma, who really is in love, realizes that it isn't working. During McClure's comeback, a great musical scene has McClure starring in "Stop the Planet of the Apes, I Want to Get Off!" 07 of 21 "Homer Alone" FOX The usually even-keeled Marge freaks out from the stress of taking care of her family and sends herself to Rancho Relaxo in "Homer Alone," which first aired on Feb. 2, 1992. Lisa and Bart stay with Selma and Patty, and Homer is left with Maggie. Marge's breakdown is familiar to any stressed out parent: She fantasizes about ordering alcohol and a hot fudge sundae from room service while relishing a bubble bath. Meanwhile, Bart's giving one of his aunts a bunion rubdown adds to the hilarity. But the scene that really pushes the episode onto this list happens after Maggie crawls away from home, and Homer can't find her. He phones the missing children hotline. When he's put on hold he hears the on-hold tune: "Baby Come Back." 08 of 21 "Homer: Bad Man" Fox "Homer: Bad Man," which originally aired on Nov. 27, 1994, tackles the topic of sexual harassment, which was then a hot issue in America—as it is to this day. Only on "The Simpsons" could viewers watch an episode that begins at a candy convention and ends with Homer narrowly proving his innocence when he's accused of sexually harassing his babysitter by showing her a video made by Groundskeeper Willie. Homer only wanted to grab the rare Gummi Venus de Milo, which was stuck to her behind—but as is often the case in the series, his buffoonishness nearly leads to dire consequences. 09 of 21 "Homer the Great" FOX "Homer the Great," which first aired on Jan. 8, 1995, features one of the series all-time best songs and a wonderful guest star. Homer is inducted into the Stonecutters, a secret and exclusive group that wields great power and influence. Top scenes include: "The Stonecutters Song—titled "We do! We do!"—and a sly joke referring to the leader as No. 1. The character is played by Patrick Stewart, aka Captain Picard from "Star Trek: The Next Generation," who referred to his second in command as No. 2. Plus, Homer using a secret tunnel to bypass a traffic jam is a genius bit of scripting. 10 of 21 "Hurricane Neddy" FOX In "Hurricane Neddy," which first aired on Dec. 29, 1996, Ned Flanders' home is the only one in Springfield destroyed by a hurricane. It shakes his faith in God and sends him to the psychiatric ward. In an "Alice in Wonderland"-like scene, Flanders tries to navigate a hallway at the facility that continually gets narrower and shorter. The episode is one of the only times Simpsons' fans witness the normally staid-and-sober Flanders crack up. The best scene, though, is Flanders' flashback to his childhood, where viewers get to see his beatnik parents. 11 of 21 "The Itchy and Scratchy and Poochie Show" FOX Another top episode is from the eighth season, "The Itchy and Scratchy and Poochie Show," which first aired on Feb. 7, 1997. During the episode, Homer is hired as the voice of Poochie, a new character on the "Itchy and Scratchy Show." Though Homer and his writers try to make the character cool and hip, Poochie is rejected. The entire story, though, is mirrored when a new character, Roy, moves into the Simpsons house. When Poochie is canceled, Roy leaves the Simpsons. The entire episode is a tongue-in-cheek take on the business of making cartoons. 12 of 21 "Last Exit to Springfield" Twentieth Century Fox "Last Exit to Springfield," which first aired on March 11, 1993, finds Homer serving as the head of the union at the Springfield nuclear power plant. Because Lisa needs braces, he fights for the employees keep their dental plan. The episode is filled with great moments, such as Ralph Wiggum being shown "The Big Book of British Smiles" to get him to brush his teeth. Then there's Homer's "train of thought" when he hears Lenny shouting, "Dental plan!" and Marge proclaiming, "Lisa needs braces!" Hearing Marge's remarks, the plant's boss, Mr. Burns, indignantly asks his assistant, "Who is that firebrand, Smithers?" 13 of 21 "The Last Temptation of Homer" Twentieth Century Fox In "The Last Temptation of Homer," which first aired on Dec. 9, 1993, Michelle Pfeiffer guest stars as Mindy Simmons, a new employee at the power plant. Homer falls for her because she's gorgeous, loves donuts, and burps frequently. In the end, Homer realizes he loves Marge too much to cheat on her. Pfeiffer is so elegant and beautiful that the irony of her playing Homer's burping love interest is funny in itself. Also, the thorny issue of adultery is tackled in a way only "The Simpsons" could, with humor and tenderness. Although Homer is contemplating cheating, he's a sympathetic and almost innocent character. Indeed, throughout the years, "The Simpsons" has handled the subject of couplehood with thoughtfulness and aplomb. 14 of 21 "Life in the Fast Lane" FOX When Homer gives Marge a bowling ball as a birthday present, she vows to take up lessons in "Life in the Fast Lane," which first aired on March 10, 1990. Initially, during an event at the local bowling alley, Marge declines a lane saying, "No thanks, I'm just here out of spite." But she finds herself attracted to the charming instructor, Jacques, played by Albert Brooks. On her way to his apartment, Marge changes her mind, and in a parody of the film, "An Officer and a Gentleman," Marge marches through the power plant to find Homer. Then Homer announces: "I'm going to the back seat of my car with the woman I love, and I won't be back for 10 minutes!" 15 of 21 "Marge vs. Monorail" FOX "Marge vs. Monorail," which first aired on Jan. 14, 1993, has many scenes and moments that are considered classic by Simpsons fans, including Lyle Lanley's "The Music Man"-inspired song and dance at the town hall meeting. The late Leonard Nimoy, who played Mr. Spock on the original "Star Trek" television show as a well as a number of films, serves as grand marshall, while a confused Mayor Quimby exclaims, "May the force be with you!"—a decidedly mixed allusion, since that saying is a cornerstone of the competing "Star Wars" films. The funniest line, however, is reserved for Homer when he is considering what to use as an anchor for the runaway train: As he is regarding Bart, Bart says, "Think harder, Homer." 16 of 21 "Mr. Plow" FOX In "Mr. Plow," which first aired on Nov. 12, 1992, Homer starts a business that, for once, becomes successful. But his snow plow business is so successful that his friend Barney starts one, too. The competition becomes fierce, but in the end, their friendship proves to be more important than money. The crowning glory is the jingle Homer composes for his late-night commercial. What fan can't sing, "Call Mr. Plow, That's my name, That name again, Is Mr. Plow?" 17 of 21 "Natural Born Kissers" FOX Homer and Marge rediscover passion when they start making love in places where they could get caught in "Natural Born Kissers," which first aired on May 17, 1998. There aren't many couples on TV who have worked as hard to stay together as these two. It's heartening to see even a cartoon couple dealing with the same issues as everyone else. The best scene takes place at the miniature golf course, with Ned, Maude and everyone else poking into the windmill where Homer and Marge are hiding, trying to retrieve a golf ball. Homer and Marge flee, escaping in a hot air balloon. During the ride, Homer winds up hanging onto the rope, being flown over Springfield in the buff. Naked Homer Simpson is always funny. 18 of 21 "Radioactive Man" Twentieth Century Fox Milhouse, one of the many supporting characters on the show, gets his 15 minutes of fame in "Radioactive Man," which first aired on Sept. 24, 1995. In this episode, Milhouse wins the part of Fallout Boy in the "Radioactive Man" movie that's being made in Springfield. But Milhouse finds that movie-making isn't much fun. "Radioactive Man" focuses on the friendship between Bart and Milhouse, which is endearing and touching. The episode also pokes fun at Hollywood very effectively. Adding to the wit of the episode, favorite characters Rainier Wolfcastle, played by Harry Shearer, and Lionel Hutz, played by Phil Hartman, also make appearances. 19 of 21 "Rosebud" FOX "Rosebud," which first aired on Oct. 21, 1993, focuses on Mr. Burns. Burns searches for a stuffed bear from his childhood, Bobo. When he discovers Maggie's bear is Bobo, he offers the Simpsons $1 million in exchange for the toy—but Homer refuses to take the bear from his child. Burns and his assistant, Smithers, even trying unsuccessfully to steal the bear. Though Burns makes Homer's life miserable, including depriving him of TV and beer, Homer never gives in. Finally, though, sweet Maggie gives Burns the cherished bear. 20 of 21 "Selma's Choice" Twentieth Century Fox In "Selma's Choice," which first aired on Jan 21, 1993, the family goes to the funeral of Aunt Gladys, who, in her video, warns Selma and Patty that they should marry and have children before it's too late. Selma takes the message to heart. But when she takes Bart and Lisa to Duff Gardens, and it's a complete disaster, she changes her mind. "Selma's Choice" is a good example of an episode that has the Simpsons dealing with real-life issues in a humorous and touching way. Full of jokes, from the funeral home to Selma's experience with the dating service, the show handles a difficult situation in an honest and thought-provoking manner. 21 of 21 "A Streetcar Named Marge" FOX "A Streetcar Named Marge," which first aired on Oc. 1, 1992, showcases the musical talents of composer Alf Clausen and the singing talents of the cast—as well as the buff upper body of Ned Flanders. Who knew? Jon Lovitz, as director Llewelyn Sinclair, is deliciously over-the-top. Apu ending his scene as the newspaper boy on a high, sad note is pitch perfect. Maggie's covert liberation of everyone's pacifiers at the Ayn Rand School for Tots is delightfully clever.