Ana Gasteyer, a former Saturday Night Live (SNL) cast member, recently shared an unforgettable behind-the-scenes moment involving Sean ‘Diddy’ Combs (then Puff Daddy) and comedy legend Will Ferrell. During an episode of the Las Culturistas podcast on November 20, Gasteyer reminisced about a 1998 episode of SNL where Combs performed as a musical guest. The story, which highlighted a clash between comedy and celebrity ego, underscored the magic—and chaos—that often unfolds at the iconic sketch show.
Setting the Stage: SNL in 1998
In May 1998, Sean ‘Diddy’ Combs took the SNL stage to perform his hit song “Come With Me,” a dramatic reimagining of Led Zeppelin’s “Kashmir.” The track, featuring hard-hitting beats and orchestral grandeur, was part of the soundtrack for the film Godzilla. For Diddy, it was an opportunity to showcase his star power on live television. For the SNL cast, it was yet another chance to create unforgettable moments.
According to Gasteyer, Diddy’s visit to SNL wasn’t without its quirks. The rapper demanded a closed set during rehearsals—a rare request that hinted at his need for control and focus. Gasteyer humorously described the energy surrounding Diddy’s performance as “faux importance,” emphasizing the over-the-top theatrics typical of the entertainment industry.
The Birth of a Prank
During a writers’ meeting leading up to the episode, someone floated the idea of a prank involving Will Ferrell, known for his ability to stay in character and elevate any comedic situation. Ferrell, who was riding high as one of SNL’s breakout stars, was always game for a good joke. The suggestion? Crash Diddy’s rehearsal in character as “Ron,” a clueless and disoriented figure.
The concept was simple but bold: Ferrell would disrupt Diddy’s intense and dramatic rehearsal of “Come With Me” by walking onto the stage, completely oblivious to the seriousness of the moment. The plan captured the essence of SNL—a willingness to take risks for the sake of comedy.
Ferrell in Action: The Prank Unfolds
As Diddy rehearsed, Ferrell descended the stairs and walked directly onto the closed set. Staying fully in character, he wandered around the stage with a dazed expression, creating a stark contrast to Diddy’s high-energy performance. The control room caught every moment, from Diddy’s intense rapping to Ferrell’s hilariously out-of-place antics.
Gasteyer, who watched the scene unfold from the sidelines, described the moment in vivid detail. “I have the video from the control room where Sean Combs is rapping with like, 'Da-na-na, da-na-na, da-na-na,' behind him. And Ron’s walking around, looking really disoriented,” she said. The juxtaposition was pure comedic gold for the SNL cast and crew, who erupted in laughter.
The Aftermath: Diddy’s Reaction
While the prank was a hit with the SNL team, Diddy’s reaction was far less enthusiastic. Gasteyer revealed that the rapper didn’t take the disruption lightly, describing him as “very uncomfortable” during and after the incident. His serious demeanor clashed with the irreverent humor that defined SNL’s culture.
Gasteyer pointed out the irony of Diddy’s response, poking fun at the dramatic energy surrounding the performance. “He really did not roll with it,” she admitted. “But it was also just like, the artifice of all that faux importance.” Despite Diddy’s discomfort, the prank became a legendary moment among the SNL cast.
Why the Prank Resonated
The contrast between Diddy’s serious artistry and Ferrell’s absurdist humor highlighted a recurring theme at SNL—the tension between celebrity image and comedic irreverence. SNL has long been a platform where high-profile guests are expected to roll with the punches, whether it’s through participating in sketches or enduring lighthearted ribbing.
Diddy’s reluctance to embrace the joke stood out, especially compared to other musical guests who often leaned into the show’s chaotic energy. However, it also underscored the differences in creative approaches between artists and comedians. For Diddy, the rehearsal was a moment to perfect his craft. For SNL, it was another opportunity to push boundaries and create memorable television.
Gasteyer’s Perspective
Gasteyer’s retelling of the story on Las Culturistas offered a nostalgic glimpse into the unpredictable world of SNL. As a cast member from 1996 to 2002, Gasteyer was part of a golden era for the show, working alongside comedy giants like Ferrell, Molly Shannon, and Tina Fey. Her anecdotes often reflect the camaraderie and creativity that defined her time on the show.
Reflecting on the prank, Gasteyer didn’t shy away from poking fun at the entertainment industry’s self-importance. Her playful critique of the “artifice” surrounding Diddy’s performance added another layer to the story, showcasing her sharp wit and comedic sensibility.
A Moment That Lives On
Over two decades later, the prank remains a beloved memory for those who witnessed it. It’s a testament to SNL’s enduring ability to blend celebrity culture with offbeat humor, creating moments that transcend the show itself. While Diddy may not have appreciated the joke at the time, the incident is now part of the rich tapestry of SNL lore.
For fans of the show, Gasteyer’s story serves as a reminder of the unique chemistry that happens when comedy and music collide. Whether it’s a dramatic performance, a well-executed prank, or an awkward reaction, SNL continues to be a space where the unexpected is always welcome.