Kelsey Grammer has been playing Frasier off and on since 1984, a 40-year run that’s remarkable for its longevity if nothing else. But there’s another Grammer character who’s been around for nearly as long: Sideshow Bob, who debuted in 1990 during the first season of The Simpsons. “You are the king of long runs,” said Deadline’s Pete Hammond during a conversation for The Actor’s Side.

As for how he got the Simpsons gig, longtime Simpsons writer Sam Simon knew Grammer from an early stint on Cheers. “He called me one day when he was in the middle of production on The Simpsons,” Grammer said.

Simon asked him, “Are you still singing?”

Of course, Grammer was still singing. The “Tossed Salad and Scrambled Eggs” crooner was famous on the Cheers set for beginning morning rehearsals with a show tune. You know, the kind of coworker you want to...