Best Guest Stars On Seinfeld – Top 10 Appearances

6. Phil Morris as Jackie Chiles

At that point in the ‘90s, the O.J. Simpson trial was still fresh in pop culture, and Chiles was clearly patterned after one of Simpson’s lawyers, Johnnie Cochran, with his prominent mustache and flamboyant pronouncements.

Chiles could be enjoyed on another level as the writers also gave him some great lines to work with. He described Sue Ellen Mischke’s penchant for not wearing a bra as “lewd, lascivious, salacious, outrageous!” And two of the many times Kramer didn’t heed his advice led to the classics, “Who told you to put the balm on?” and “the most public yet of my many humiliations.”

5. Courtney Cox as Meryl

Played by Courtney Cox, Meryl and Jerry enjoyed pretending to husband and wife. Jerry’s having a ball saying, “my wife this,” and “my wife that.” They share pancake secrets at the diner and Meryl gets to use Jerry’s Dry-Cleaning discount. Cox is one of the best guest stars on Seinfeld.

Problems arise when Jerry decides to play the same game with another girl and in typical Seinfeld fashion, that’s the end of Meryl.

4. Peter Crombie as Crazy Joe Davola

One could make the argument that all the main characters in Seinfeld could be locked up for being sociopathic loons, but Crazy Joe Davola was the only individual on the show who was legitimately crazy – and it resulted in some fantastic material.

His connection to Pagliacci The Clown and his relationship with Elaine led to what could honestly be called some of the best real tension in the series’ history.