Will Ferrell once pranked Diddy during ‘SNL’ rehearsal: “He really did not roll with it”

Will Ferrell once pranked Diddy during a rehearsal for Saturday Night Live.

Ana Gasteyer, who appeared on the show from 1996-2002, recalled the moment that took place in 1998 on the latest episode of Bowen Yang and Matt Rogers’ Las Culturistas podcast.

At the time, Diddy was the show’s musical guest and he “demanded a totally closed set”, according to Gasteyer, for a run-through on Thursday which involved him rehearsing his track ‘Come With Me’ featuring Jimmy Page, which samples the Led Zeppelin‘s ‘Kashmir’.

During this period, Ferrell used to imitate a crew member named Rob, who had recently been fired by the director of the show’s pre-taped segments.

After being encouraged to interrupt Diddy’s rehearsal by the show’s writers, Ferrell “went on down the stairs and he marched right in,” Gasteyer said before adding: “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 added: “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?”

Ferrell discussed the moment in 2020 for the SNL series Stories From The Show, which includes footage of him crashing Combs’ rehearsal. You can view it above. “I didn’t really know what to do once I got up there,” Ferrell recalled at the time, noting that Ron also made an appearance during the closing credits of that episode.

Meanwhile, Diddy – real name Sean Combs – 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 was later denied bail having offered a $50million (£38.4m) bond, and was reportedly placed on suicide watch as he awaits trial. The artist has since appealed against the bail denial and has a trial date scheduled for May 5, 2025.

Earlier this week, another wave of sexual misconduct lawsuits were filed against the rapper. He denied these fresh claims of sexual misconduct through his reps, with his media team telling Rolling Stone in a statement: “As his legal team has said before, Mr. Combs has full confidence in the facts and the integrity of the judicial process.”