Sunday, Feb 15, The Simpsons airs its 800th episode, extending its reign as the longest-running scripted primetime series in TV history. The landmark episode, titled “Irrational Treasure,” premieres on the television schedule on Feb. 15 at 8 p.m. ET/PT on Fox, kicking off a historic doubleheader.
Since debuting as a standalone series on Fox in 1989, the animated juggernaut created by Matt Groening has become the longest-running scripted primetime series in TV history. It has outlasted presidents, formats and entire eras of television. And somehow, Springfield keeps going.
With the milestone episode airing this week, it’s the perfect time to look back at seven of the best episodes ever — the ones that defined the show’s golden age, showcased its emotional depth and proved why Homer, Marge, Bart and Lisa remain cultural fixtures.
It’s rare for a TV series to become generational infrastructure. The Simpsons did that somewhere around Season 8 — and just kept going. It’s the perfect time to queue up your Disney+ subscription and revisit seven of the greatest episodes ever made.
1. “Cape Feare” (1993) - Season 5/Episode 2
If you want peak Sideshow Bob, this is it.
After Bob is granted parole, the Simpsons enter witness protection, but Bob stalks the family with operatic intensity. The episode brilliantly parodies Cape Fear, complete with rakes, show tunes and one of the greatest extended gags in series history.
It’s dark, theatrical and packed with jokes that land decades later.
2. “Marge vs. the Monorail” (1993) - Season 4/Episode 12
Written by Conan O’Brien, this episode is controlled chaos at its finest.
After Springfield receives a financial windfall, the town builds a flashy monorail system. Homer becomes a conductor. Predictably, everything spirals.
From Lyle Lanley’s musical number to Homer’s escalating incompetence, this episode captures the show’s ability to blend satire, absurdity and heart into one perfectly timed ride.
3. “Stark Raving Dad” (1991) - Season 3/Episode 1
One of the most talked-about episodes in the show’s history.
Homer ends up in a mental hospital and befriends a white man who believes he is Michael Jackson. The episode mixes celebrity culture satire with an unexpectedly tender birthday subplot between Bart and Lisa.
Though the episode has been removed from streaming platforms in recent years, it remains one of the series’ most discussed early installments.
4. “Trilogy of Error” (2001) - Season 12/Episode 18
Proof that the show’s later seasons still had inventive firepower.
This Rashomon-style episode retells the same day from Homer’s, Lisa’s and Bart’s perspectives. Homer rushes to reattach a severed thumb. Lisa races to win the science fair. Bart gets tangled in an illegal fireworks scheme.
The episode’s clever structure and interlocking storylines show how creatively ambitious the series could be well into its second decade.
5. “Marge Be Not Proud” (1995) - Season 7/Episode 11
Not every classic relies on big satire.
When Bart is caught shoplifting before Christmas, Marge’s quiet disappointment cuts deeper than any punishment. The episode explores guilt, parental trust and emotional distance in a way few animated comedies dared at the time.
The final scene, simple and heartfelt, remains one of the show’s most powerful moments.
6. “Mountain of Madness” (1997) - Season 8/Episode 12
Homer and Mr. Burns trapped together in a snowed-in cabin? Yes, please.
During a corporate retreat gone wrong, the bitter boss and his most incompetent employee must rely on each other to survive.
The episode distills one of television’s greatest antagonistic relationships into a claustrophobic comedy about pride, ego and survival.
7. “The Way We Was” (1991) - Season 2/Episode 12
Before the chaos, there was young love.
In this flashback episode, Homer and Marge tell the story of how they met in high school. It’s awkward, sweet and surprisingly sincere.
The episode helped establish that beneath the satire, the series always had a beating heart centered on a flawed but enduring marriage.
With its 800th episode airing Sunday, 15 Feb on Fox, The Simpsons continues to evolve while honoring its legacy.
And for those who want to revisit the classics — or binge the entire run — all seasons of The Simpsons are available to stream with a Disney+ subscription.
Eight hundred episodes in, Springfield still isn’t done.
