Will Ferrell once pranked Diddy when the rapper appeared on Saturday Night Live, and it did not go over well.
Ana Gasteyer, who was a cast member of the show between 1996 and 2002, appeared on the Nov. 20 episode of Bowen Yang and Matt Rogers' Las Culturistas podcast. During her time there, she recalled how the prank went down on a 1998 episode of the sketch show.
At the time the show aired, Diddy was the musical guest and already had strong demands like having a closed set, Gasteyer says. For a run-through on the Thursday before the show on Saturday, which involved Diddy rehearsing his track "Come With Me" featuring Jimmy Page, Ferrell imitated a crew member named Ron.
The actor was encouraged to interrupt Diddy's rehearsal by the show's writers. Gasteyer recalls that Ferrell "went on down the stairs and he marched right in."
"I have the video from the control room where Sean Combs is like, rapping ... [and] behind him, Ron's like walking around looking really disoriented," she said.
"It is the greatest thing that's ever happened because what a deserved person to have their 'Kashmir' moment interrupted by Ron. And he [Diddy] really did not roll with it. He was very uncomfortable. But it was also just like, the artifice of all that faux importance. Like, what's going to happen?" Gasteyer added.
Ferrell previously discussed the moment that he interrupted Diddy during a 2020 special called SNL series Stories From The Show, which includes footage of him crashing Combs' rehearsal.
"I didn't really know what to do once I got up there," Ferrell said.
Meanwhile, Diddy is currently facing over two dozen lawsuits, while he's also battling a criminal prosecution and has been held in a federal jail in Brooklyn since his arrest on September 16.
He has been charged with sex trafficking, racketeering and transporting for prostitution, and has pleaded not guilty to all charges. He trail date is set for May 5, 2025.
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