For three decades our screens have been filled with the mishaps, schemes and dramas of The Simpsons. They’ve become a staple in the American cultural landscape, with sharp satirical storylines, unforgettable gags, and even the ability to predict the future.
Originally created as a cartoon short by Matt Groening for Fox’s Tracey Ullman Show in 1987, it began airing regularly in January 1990. It’s gone on to win multiple awards and critical acclaim, becoming the longest-running American animated series. With well over 700 episodes of the FOX comedy in the bank, it’s almost impossible to know where to start streaming.
We’ve selected some of the best episodes of The Simpsons to get you hooked, with the latest now being aired on FOX and available through DIRECTV.
Season 8, Episode 23 | First aired May 4, 1997 | Watch ‘Homer’s Enemy’ now
The Simpsons has at times divided fans, which is all part of its charm. Homer’s Enemy was one of those episodes. It centers around Frank Grimes (voiced by Hank Azaria), a man who has struggled in life but worked hard to get to where he is. He gets a job at Springfield’s power plant, but is horrified by Homer’s laziness and ineptitude. Grimes can’t handle it and eventually has a breakdown leading to a sudden and shocking death. It’s one of the sitcom’s more cuttingly intelligent episodes, as hidden beneath the dark comedy is a deeper message of self-acceptance.
Season 5, Episode 2 | First aired Oct 7, 1993 | Watch ‘Cape Feare’ now
A nod to the psychological thriller Cape Fear, this episode features the formidable Kelsey Grammer as Sideshow Bob. Bart is being sent threatening letters written in blood, with all eyes on recently paroled Sideshow Bob as the suspect. The Simpsons (now the Thompsons) are taken into witness protection but Bob is one step ahead.
‘Marge vs. the Monorail’
Season 4, Episode 12 | First aired Jan 14, 1993 | Watch ‘Marge vs. the Monorail’ now
Marking a shift from the Fox show’s established formula, Marge vs. the Monorail took The Simpsons to a new level, with its huge scale and absurdist humor. It’s ultimately a cautionary tale of a town that gets too greedy and ends up in their own disaster movie. Using the power of song, charming conman Lyle Lanley convinces Springfield to spend $3 million on a monorail, chaos obviously ensues and it’s up to Homer to save the day. A homage to The Flintstones, The Music Man and a load of disaster films, this episode is a triumph.
‘Who Shot Mr. Burns?’
Season 6, Episode 25 | First aired May 21, 1995 | Watch ‘Who Shot Mr. Burns?’ now
Unlike any others that came before it, this was a two-parter whodunnit with a cliffhanger ending that would leave fans in suspense until the next season. The show’s villain Mr. Burns has alienated much of Springfield after stealing oil that was found underneath Springfield Elementary. One night, he’s discovered with a bullet wound, and everyone’s left asking, who shot him?
‘Forgive and Regret’
Season 29, Episode 18 | First aired April 29, 2018 | Watch ‘Forgive and Regret’ now
One of the more touching episodes of the newer seasons, Forgive and Regret focuses on Homer and his father Abe’s rocky relationship. Abe confronts the guilt he feels over a past mistake that broke the relationship with his son. Their reconciliation is sweet and poignant. Worth a watch if you want to get a taste of The Simpsons’ heartfelt storytelling.
‘Homer at the Bat’
Season 3, Episode 17 | First aired Feb 20, 1992 | Watch ‘Homer at the Bat’ now
Burns places a $1 million bet on the plant softball team’s league final, so decides to hire nine professional MLB players – Roger Clemens, Wade Boggs, Ken Griffey, Jr., Steve Sax, Ozzie Smith, José Canseco, Don Mattingly, Darryl Strawberry and Mike Scioscia. But they all fall off the roster, until Homer is the only one left on the bench. Of course, he still manages to save the day. Even if you don’t know anything about baseball, or even like the sport, this is one of the silliest and light-hearted episodes.
‘Brick Like Me’
Season 25, Episode 20 | First aired May 4, 2014 | Watch ‘Brick Like Me’ now
For something a little different, check out this Simpsons alternate reality where the family and the town of Springfield are transformed into a Lego version of themselves. It’s a simple entertaining tribute to all things Lego – solving puzzles and fighting off villains – and a nice visual change from the usual Simpsons animation.
‘The President Wore Pearls’
Season 15, Episode 3 | First aired Nov 16, 2003 | Watch ‘The President Wore Pearls’ now
Lisa becomes student body president of Fairfield Elementary School in an episode that parodies the musical Evita – she even sings “Don’t Cry for me Argentina” once she’s risen to power. It’s a smart satire of the musical and a detailed exploration of Lisa’s character, touching on her darker sides and weaknesses. Filled with funny gags like any of the great episodes, it stands up as a great character study, and even features a cameo from filmmaker Michael Moore.
‘You Only Move Twice’
Season 8, Episode 2 | First aired Nov 3, 1996 | Watch ‘You Only Move Twice’ now
Homer quits his job and goes to work for a classic Bond-style villain Hank Scorpio. Voiced by Albert Brooks, Scorpio is remembered as one of the top cameo characters of the Fox show. The episode bridges the absurd with great character writing and memorable gags: the evil super villain, hammock jokes, musical chairs with more chairs than people.
‘Treehouse of Horror IV’
Season 5, Episode 5 | First aired Oct 28, 1993 | Watch ‘Treehouse of Horror IV’ now
Four is one of the best Treehouse episodes – the annual series of special Halloween-themed shows. Homer has sold his soul to the devil for a donut, but gets it back by proving he’s pledged his soul to Marge. It’s equally as weird as it is heartwarming, and like many episodes pays homage to past cultural greats – from The Twilight Zone to Dracula. And for a bit spookier fun, you can stream any other Treehouse episodes online too.
‘The Springfield Files’
Season 8, Episode 10 | First aired Jan 12, 1997 | Watch ‘The Springfield Files’ now
In a brilliant ode to the X Files, this episode follows FBI Special Agents Mulder and Scully after Homer claims to have seen an alien in the woods. Everyone writes it off as another drunken hallucination, but Homer is adamant and won’t give up the investigation. Another excellent crossover, the episode is narrated by Leonard Nimoy (best known for playing Star Trek’s Spock).
Where to watch The Simpsons on DIRECTV?
Watch these shows and your other favorite animated comedies on DIRECTV by choosing from a variety of packages. Make sure to check the channel lineup when selecting your TV package.
DIRECTV lets you connect via satellite or internet, so whether you’re looking for comedies, family shows, live TV or On Demand movies – we’ve got the right shows for you.
The content featured on https://www.directv.com/insider/ is editorial content brought to you by DIRECTV. While some of the programming discussed may now or in the future be available affiliates distribution services, the companies and persons discussed and depicted, and the authors and publishers of licensed content, are not necessarily associated with and do not necessarily endorse DIRECTV. When you click on ads on this site you may be taken to DIRECTV marketing pages that display advertising content. Content sponsored or co-created by programmers is identified as "Sponsored Content" or "Promoted Content."