The Simpsons has featured some pretty harsh celebrity burns over the years — from poking fun at John Travolta’s struggling career (less than two weeks before the release of Pulp Fiction), to lampooning Robert Downey Jr.’s legal troubles, to McBain’s brutal stand-up comedy routine about Woody Allen.
On the other hand, the celebrity guest stars who offer to voice cartoon versions of themselves on the show seem to get treated pretty well. Although Mark Hamill wasn’t crazy about the show’s suggestion that he makes personal appearances in his Star Wars costume for money.
Even harsher was the show’s portrayal of legendary talk show host Dick Cavett. In the Season Six episode “Homie the Clown,” Cavett is the host of Springfield’s Regional ACE Awards. A notorious name-dropper, Cavett ends his monologue by bluntly telling the audience, “I know Woody Allen” to a smattering of tepid applause.
He then tries to schmooze with “Krusty,” who’s actually Homer in disguise, by bragging that he has some “wonderful stories about other famous people that include me in some way.” As Homer tries to evade him, Cavett remarks that his “churlish attitude reminds me of a time I was having dinner with Groucho.” The scene ends with Homer threatening to punch poor Cavett in the face.
“I think this probably is … the meanest we ever were to a guest star,” Simpsons producer David Mirkin admitted on the episode’s DVD commentary. “And Dick was a fantastic sport about it. We made really nasty fun of Dick, and we love him, but we did make good fun of him.”
“Dick has a tendency – he knows a lot of famous people, he knows Groucho, he knows Woody Allen. And he always tells stories that involve them with him,” Mirkin continued. “And so I used that observation in here. And he didn’t have any kind of a problem with it. He was happy to do it.”
Despite ridiculing this particular aspect of Cavett’s personality, the Simpsons team were all big fans of the host. Mirkin called him a “great guy and a great sport” and Matt Groneing offered his possibly “controversial” take that The Dick Cavett Show was “maybe the best talk show of the 1970s.”
The Simpsons creator specifically praised the oddball celebrity panels, recalling an episode in which surrealist painter Salvador Dali placed a live anteater on silent film star Lilian Gish’s lap.
The writers’ admiration for Cavett is probably the reason why the jokes seemed so mean in retrospect. After all, none of them seemed at all remorseful about hiring Tom Arnold for an episode in which humanity is so fed up with Tom Arnold that they condemn him to die in outer space.