Bart gets Hit By a Car (Season 2)
One of the first episodes to delve into the depths of C. Montgomery Burns' true evil. Better yet, it features the first appearances of Springfield sleazeballs Dr. Nick Riviera and attorney Lionel Hutz (voiced by the late Phil Hartman).
Flaming Moe's (Season 3)
An early classic featuring a precursor to sizzurp...and some memorable Cheers references.
Homer at the Bat (Season 3)
Burns hires a group of MLB ringers for the company softball team. Still one of the show's most cameo-heavy episodes.
The Otto Show (Season 3)
Bart and Lisa's deadbeat bus driver moves in with the Simpsons. Noteworthy as one of the first episodes to focus mainly on one of Springfield's ancillary characters. There's also a brilliant Spinal Tap cameo.
A Streetcar Named Marge (Season 4)
Marge performs in a campy musical version of "A Streetcar Named Desire." For many of us, a first introduction to the Tennessee Williams stage classic.
Treehouse of Horror III (Season 4)
It was nearly impossible to pick a favorite from the show's iconic Halloween episodes. So we went with this one because it features cursed frozen yogurt.
Mr. Plow (Season 4)
Homer gets into the snow removal business and accidentally unearths the ambitious side drinking buddy Barney.
Marge vs. The Monorail (Season 4)
Considered by many to one of the show's finest. Written by future late night staple Conan O'Brien.
Last Exit to Springfield (Season 4)
Yet another season 4 classic. All we have to say is, "Dental plan! Lisa needs Braces!"
Homer's Barbershop Quartet (Season 5)
One of the show's finest flashback episodes, featuring some memorable musical numbers. "There was nothing in Al Capone's vault, but it wasn't Geraldo's fault!"
Homer Badman (Season 6)
A topical episode that still holds up 20 years later. We all elarned a valuable lesson about the gummy Venus de Milo.
22 Short Films About Springfield (Season 7)
One of the show's most experimental installments. Fun fact: it had 11 credited writers.
El Viaje Misterioso de Nuestro Jomer (The Mysterious Journey of Homer) (Season 8)
Did we say the last one was bit unusual? This episode has Johnny Cash voicing a mystical coyote. What more do you need?
The City of New York vs. Homer Simpson (Season 9)
Homer pisses off the Big Apple. Seldom re-run these days due to some pre-9/11 jokes at the expense of the World Trade Center.
Homer to the Max (Season 10)
Homer changes his name and briefly becomes cooler. Naturally, it doesn't last.
The Mansion Family (Season 11)
The Simpsons house-sit for Mr. Burns. It ends about as well as you'd expect.
HOMR (Season 12)
A crayon that's been lodged in Homer's brain is removed, causing him to become hyper-intelligent. Yet, again it thankfully doesn't last.