25 of The Craziest Simpsons Guest Stars

Sure, “The Simpsons” may have lost a step over the last…decade or so. Even still, it entices big star after big star to make cameos in its yellow Springfield universe. Some stars have been better than others, and then even some others have been outright crazy. To find the wackiest of the wacky, take a look at this list of the 25 craziest Simpson’s guest stars of all time.

Albert Brooks.

The man with the most guest shots on the Simpsons, not counting recurring characters. His best role? Hank Scorpio in the episode “You Only Move Twice.”

Bette Midler.

The Divine Miss “M” is at her crazy best in Season 4′s “Krusty Gets Kancelled.

Kelsey Grammer.

The man who was Frasier has turned in countless crazy performances as Sideshow Bob.

Michael Jackson.

Poor Saxy boy. Locked up in Springfield jail forever, all because he couldn’t keep his mouth shut.