Kelsey Grammer Reveals How He Got the Sideshow Bob Gig on ‘The Simpsons’

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 slug in the mouth if you haven’t had coffee yet. 

“So he said, ‘Can you sing a Cole Porter song?’ I said, ‘Well yeah, of course I can. Which one?’ And he said, ‘Every Time We Say Goodbye.’ I thought, ‘Yeah, yeah, I’ll do that for you.’ And that was the foundation of Sideshow Bob.”

But that’s only the beginning of the character’s origin story. “When I got in and started to read the part, I had logged away a character from an experience in my past. Ellis Rabb.”

Rabb was a formidable name in theater circles. He was the force behind the Association of Producing Artists, a theater company that brought new plays and worthy revivals to Broadway and regional playhouses.  

Early in Grammer’s career, he got a side job painting Rabb’s office. “I was working on the office space for a while and so I got to know Ellis,” Grammer explained. “And the way he spoke was pretty remarkable, so I would just sort of drink it in. He‘d come in late in the afternoon while I was still working.”

“Oh Kelsey, wouldn‘t you like to sit and have a drink with me?” Rabb would ask.

“Sure, I’d love to. Why not?” Grammer replied. “I‘m just about done here. Let me close up the paint cans and clean my brushes, and I‘ll sit down and have a martini with you.”

And so they’d drink. Grammer told the story of how Rabb had been married to Rosemary Harris years before, even though he was “beyond any working definition of gay.” Despite his sexual preferences, Grammer said that Rabb and Harris had a wonderful relationship. “Well, it was that generation.”

After the couple split, Harris went on to marry a senator from Washington with whom she had a child. That was the subject of one of Rabb and Grammer’s martini conversations. Grammer imitated Rabb’s sad lament, spoken in perfect Sideshow Bob elocution: “Oh Kelsey, that baby should have been mine.” 

And that, explained Grammer, is Sideshow Bob. 

There aren’t many video clips of Rabb on YouTube, but this one does the trick. Close your eyes and you can hear that Grammer wasn’t kidding about the character’s origins.