DeVito played it mostly straight as his company was brought down by Homer’s terrible design decisions. Years before Frank Grimes showed what the real world would think of the Simpson family, Homer was brought down to Earth by his own newfound brother, Herb. Seymour Skinner: “Well, I guess you had to be there.” Marge Simpson: “That’s not a funny story.” And since ‘77 I’ve been making sneakers at gunpoint in a sweatshop in Boo-Haun.” camp, I was sold to China for slave labor. That doesn’t mean that Sheen doesn’t deserve respect for doing an admirable job on a thankless task, but let’s follow Mayor Quimby’s advice and never mention this episode again. Though Sheen’s stunt-casting of a long-lost Vietnam vet was meant to recall his roles in movies like Apocalypse Now, his turn as the “real” Seymour Skinner came to represent what many fans considered to be the series shark-jumping moment. Though at the time Howard had the most experience in comedy, Baldwin showed a pre- 30 Rock knack for timing that definitely carried over to his misadventures with Liz Lemon.īaldwin: “We’d want another chance if one of us made a bad film, right?” Alec Baldwin, Kim Basinger and Ron Howardīack when they were still together, Baldwin and Basinger proved solid comic foils for Homer’s starstruck antics. You expect rock stars to do wild and crazy things, but there’s something about a PBS mainstay threatening murder that makes this cameo great. In an episode that also stars Kid Rock and rapper Joe C., the restrained Rose easily comes out as the bright spot. Jacques: “You’d love it, it’s not quite breakfast, it’s not quite lunch, but it comes with a slice of cantaloupe at the end.” One of his early roles is one of his best: The slimy Frenchman Jacques, who tries in vain to woo a weary Marge away from her dopey husband. Part of a select circle of Simpsons guest stars that have appeared on the show more than a half-dozen times, Brooks is a series staple. You won’t see psuedo-cast members like the late Phil Hartman or Marcia Wallace on here, but otherwise your favorite will probably be making an appearance. This list could easily be twice as long, but after going through the show’s 25 seasons, we’ve narrowed The Simpsons’ gargantuan guest star roster down to its 100 best. And while there have certainly been a few duds over the years, among the rest are some of the funniest guest spots in the history on television. Over the course of two and a half decades and more than 500 episodes, The Simpsons has seen its fair share of celebrity appearances and then some, rivaled only by Saturday Night Live as America’s premier destination for stars looking to poke fun at themselves.

Someday I'll Kill You by Hugh Desmond