‘He of course, like, shut down the whole building’: The one time Will Ferrell broke Diddy’s strict rules and the rapper ‘did not roll with it’

Here’s a shocker: Sean “Diddy” Combs was never a chill guy. While he’s now sitting in a cold prison cell wondering how it all went wrong, there was a time in the late 1990s when he was practically untouchable. He used that fame and power to close the set of Saturday Night Live when he performed on the show, and Will Ferrell couldn’t help but completely violate that. Diddy’s response? Not a good one.

This juicy anecdote about Diddy and Will Ferrell comes to us courtesy of former cast member Ana Gasteyer. She appeared on the popular Las Culturistas podcast and shared that when Diddy came to do the show, “he of course, like, shut down the whole building.”

Gasteyer, who was on the show from 1996 to 2002, explained to hosts Matt Rogers and Bowen Yang that it was really rare for someone to come to SNL and ask for a closed set.

“You can tell like the five assholes in the six years that I was there when they would be like, ‘So and so is in the building, everybody stay in your dressing rooms!'” This would be appropriate for say a presidential candidate, she said, “But apart from that, really, it’s my house.”

Diddy was in the building with Led Zeppelin guitarist Jimmy Page performing the song “Come with Me,” which sampled the legendary band’s legendary song “Kashmir.” The song was a top ten hit at the time but quickly fell off the charts. It is not remembered fondly.

In fact, Chuck D from Public Enemy gave a rather vitriolic take on the song: “I like Jimmy Page and P. Diddy, but what they did to ‘Kashmir’ was a debacle. They are giants in their own way – and you can print this – but that was a fucking travesty”, he told Rolling Stone. “When I get involved with a classic, I knock the f*cking ceiling out of it or I leave it the f*ck alone.”

On the Thursday before the Saturday show, Diddy was rehearsing with Page and the New York Philharmonic. Ferrell had been doing an ongoing bit where he dressed up as a former crew member on the show named Ron. As part of the bit, he purposely ignored Diddy’s request for a closed set.

“They were like, ‘Wouldn’t it be so funny if Ron just went in?’ And he did! He went on down the stairs and he marched right in,” Gasteyer said. “And I have the video from the control room where Sean Combs is rapping with like, ‘Da-na-na, da-na-na, da-na-na, da-na-na’ behind him. And Ron’s walking around, looking really disoriented.”

Gasteyer went on to say that it “Was the greatest thing that ever happened” and that Diddy deserved to have his moment interrupted by Ron just for the sake of trying to control everyone around him.

However, he “really did not roll with it,” she said. “He was very uncomfortable, but it was also just like, the artifice of all that faux importance. Like what’s gonna happen? You’re gonna walk into the studio and you’re gonna be like, ‘I’m in the studio. I work here.’?”