In a revelation that is both surprising and relatable, Conan O'Brien, the highly accomplished comedian and late-night talk show host, has opened up about his time working on Saturday Night Live (SNL) from 1988 to 1991, expressing regret over his intense approach to the job. During a recent episode of his podcast, Conan O'Brien Needs a Friend, O'Brien candidly shared, “I regret being so intense about that job. I was way too intense, and I think I robbed myself of some fun that I could have had.”

Despite having a career filled with achievements and iconic moments, O'Brien reflected on how his drive for perfection might have limited his enjoyment of the experience. While he did have fun, he believes that a lighter touch could have led to even more memorable moments and perhaps a longer tenure on the prestigious show.

The conversation took an entertaining turn when O'Brien's guest, none other than Oscar-winning actor Tom Hanks, reminisced about their time at SNL, noting, “The first year I was on SNL, I called you the Boiler Room Boys.” Hanks, who has hosted SNL multiple times, playfully inquired about O'Brien's departure from the show, joking, “Did you get fired, Conan?” O’Brien humorously attributed his exit to burnout rather than any official firing, claiming, “No, I burnt out. I was like, ‘I've got to go,’ and that’s when I went to The Simpsons.”

Jumping to 1991, O'Brien transitioned to a writing and producing role at The Simpsons, one of Hollywood's most coveted positions at the time. His talent did not go unnoticed, leading Lorne Michaels, the legendary producer behind SNL, to offer him the hosting gig for Late Night in 1993. O’Brien hosted the show successfully until 2009, cementing his place in late-night television history.

So what made writing for The Simpsons and hosting his own late-night show easier than the demanding environment of SNL? Hanks suggested it might be “the creative atmosphere,” where writers had the opportunity to bring their sketches to life on the spot, contrasting this with the high-pressure situation SNL often presented. It’s a world where anxiety could run high, with writers sweating bullets over their performances.

O'Brien also highlighted the unique challenges of SNL, noting the immense pressure placed on writers and performers to create and execute sketches in real-time. He shared a humorous anecdote from his own early days, describing how daunting it was to take charge of directing icons like Steve Martin without much experience or confidence. “I thought, ‘I’m 26, I’ve never even been to a restaurant!’” he recalled with a laugh.

Moreover, Hanks, a member of the esteemed SNL Five-Timers Club, elaborated on the show's physical demands. He even jokingly recounted how, during his last hosting experience, he aimed to minimize his movements, saying, “It’s a young man's game… No, no, no. Take it easy, Tom.” This piece of advice underscores the grueling nature of SNL and the need for both physical and mental resilience in such a fast-paced environment.

Conan O’Brien's reflections provide an unexpected glimpse into the pressures of comedy writing on live television, showcasing that even the most successful figures grapple with doubts and regrets. His journey serves as a reminder that while ambition is crucial, it's important to balance it with joy and creativity. After all, in the world of comedy, capturing the moment often means savoring it too.