Will Ferrell Trolled Diddy When He Tried to Shut Down an ‘SNL’ Rehearsal

Ana Gasteyer figures she encountered only five a-holes in her six years at Saturday Night Live, she said this week on the Las Culturistas podcast. The way she could tell? “They would be like, ‘So-and-so is in the building, everybody stay in your dressing rooms!'” 

That’s exactly what went down the week Sean “Diddy” Combs showed up as a musical guest in 1998. “He, of course, shut down the whole building,” she said. “Which is applicable if you’re a presidential candidate. But apart from that, really it’s my house. He demanded a totally closed set.”

In 1998, SNL was also Will Ferrell’s house. Gasteyer remembers how Ferrell, as a goof, would walk around as a character named Ron. “They were like, ‘Wouldn’t it be so funny if Ron just went in?’” she said — and that’s just what Ferrell did. “He went on down the stairs, and he marched right in. And I have the video from the control room where Sean Combs is rapping and behind him, Ron is just walking around looking really disoriented.”

Diddy took the interruption just the way one would expect. “He really did not roll with it,” Gasteyer said. “He was very uncomfortable.”

Ferrell himself reminisced about Ron’s visit to Diddy in a 2020 installment of SNL Stories from the Show. Ron, he said, was “this character that I came up with with a fake mustache and an ascot and this weird outfit that I found at a thrift store.” 

Ron would walk around the SNL set, Ferrell never breaking character. The oddly dressed man supposedly worked the second camera unit for SNL director Jim Signorelli, while doubling as his nanny. You never knew where Ron might turn up, but you could count on the character to be “really annoying.”

Several SNL cast and crew members were watching Diddy rehearse (Ferrell called him Puff Daddy) when someone suggested Ron should join the musical guest onstage. “And before everyone turned to see, I had sprinted out the door,” Ferrell revealed. “It’s supposed to be a closed set.”

“I didn’t really know what to do once I got up there,” Ferrell said as he reviewed low-grade footage of the rehearsal. “Oh — then we shook hands. That was good.”

But Ron wasn’t quite done with Diddy yet. “If you go back and look at the goodnights of that show, Ron might be in the goodnights,” Ferrell said with a smirk. “I just have a feeling.”