What Are the Five Best ‘Simpsons’ Episodes of All Time?

“D’oh!” That’s the only appropriate response to the question: What’s the best Simpsons episode of all time? Despite the enormity of the question, Vanity Fair’s television analysis podcast Still Watching will attempt to answer the question with a three-part series that will culminate with hosts Hillary Busis, Richard Lawson, and Chris Murphy ranking the top five Simpsons episodes of all time. Crack open a Duff beer and find out if your favorite Simpsons episode made the cut.

The Simpsons has been the standard bearer for comedy ever since it premiered on Fox on December 17, 1989. Created by Matt Groening and developed by Groening, James L. Brooks, and Sam Simon, The Simpsons has satirized American suburban life by way of the hilarious hijinks of married couple Homer and Marge Simpson; their children Bart, Lisa, and Maggie; and the citizens of Springfield for more than three decades. Thirty-five seasons later, The Simpsons is still producing new episodes, making it the longest-running animated series, longest running sitcom, and longest running scripted prime time television series in America.

So, out of 768 potential episodes, what Simpsons episodes are in Still Watching’s running for the best Simpson’s episode of all time? The first contender is the season five, episode two “Cape Feare,” which premiered on October 7, 1993. Written by the iconic John Vitti, “Cape Feare” is an all-time classic featuring one of The Simpsons’s best recurring characters, Sideshow Bob, voiced by Kelsey Grammer. As Sideshow Bob plots to murder Bart after getting released from prison, the Simpsons go into the witness protection program as “The Thompsons.”

“Cape Feare” is Busis’s favorite Simpsons episode of all time, but all three hosts hosts agree that it displays the best of what The Simpsons has to offer: marrying true absurdity (Sideshow Bob stepping on rakes bit is an all-timer) and shrewd satire (in this case of Martin Scorsese’s film Cape Fear). And for the musical theater loving hosts, the climax invoking Gilbert and Sullivan’s HMS Pinafore was just icing on the cake of a delicious episode.

The next contender is the season seven, episode 14, “Scenes From the Class Struggle in Springfield,” which aired on February 4, 1996. It was written by Jennifer Crittenden and followed Marge as she impulsively purchases a Chanel dress at a consignment store and then becomes obsessed with joining Springfield’s exclusive country club. Murphy’s favorite episode, “Scenes From the Class Struggle in Springfield” stands out for its incisive and cutting class commentary—an important and sometimes overlooked hallmark of The Simpsons. From Marge working overtime to fit in with in-crowd at the country club at the expense of her family to moneybags Monty Burns not knowing he was bad at golf because his underling always cheated for him, “Scenes From the Class Struggle in Springfield” expertly skewers the elite.

The final episode mentioned in Part One of Still Watching’s Simpsons series is season six, episode eight, “A Millhouse Divided,” which aired December 1, 1996. Written by Steve Tompkins, the episode focuses on side character Millhouse’s parents, LuAnne and Kirk VanHouten, who after a terrible game night at the Simpson household decide to get divorced. LuAnne’s glow up compared to Kirk’s spiral is played for maximum comedic effect until the very end of the episode where, for one brief moment, it looks as if Kirk is going to win back his estranged wife. (He does not.) “A Millhouse Divided” highlights The Simpson’s expert word-building, devoting an entire episode to a secondary character’s parents and making it one of the best episodes of the series. While things don’t end well for LuAnne and Kirk, “A Millhouse Divided” is also a wonderful Homer and Marge episode highlighting Homer’s underlying sweetness and affection for Marge underneath his idiocy.

How would you rank those three Simpsons episodes? And what other episodes should be in contention for the best Simpson episode of all time? Listen to the full conversation above or wherever you download podcasts. Stay tuned to see what other Simpsons episodes crack the top five, and email [email protected] with questions, comments, or your favorite Simpsons episode.