For many comedy writers, working at Saturday Night Live would be the ultimate career accomplishment. But for Conan O'Brien, his tenure was filled with regret.
O'Brien's time at Saturday Night Live was really just the beginning of his career. His talent ensured it was a launching pad and not a peak. He went on to write for The Simpsons and later became perhaps the most beloved late-night TV host in the genre's history. Add in a successful podcast, travel show, and plans to host the Oscars, and O'Brien's made a pretty nice career for himself since leaving SNL.
However, O'Brien's career could have looked much different had he taken a different approach to his job at Saturday Night Live. He explained his regrets to Tom Hanks during a November 2024 episode of Conan O'Brien Needs a Friend.
"“People always say no regrets. I regret being so intense about that job. Yeah. I was way too intense, and I think I robbed myself of some fun that I could have had. I did have a lot of fun, but I think I could have had more fun. And I think I could have maybe written there a little longer if I didn’t make it such a grind for myself.”"
O'Brien also admitted that he burnt out at Saturday Night Live. There are countless stories about the unnatural hours required to be successful at SNL. And O'Brien has also discussed at length how he approached his education leading up to attending Harvard as a grind. So clearly, O'Brien's personality (at least at that time) was one that didn't allow him to fully enjoy the fruits of his labor.
The comedian also praised SNL creator Lorne Michaels for treating O'Brien with care. And the SNL boss took things a step further when he tapped O'Brien to replace David Letterman as host of Late Night just a few short years after Conan left SNL.
For the time he was at Saturday Night Live, O'Brien left his mark. The 2024 Christmas episode began with a Five Timers Club sketch featuring Tom Hanks and comedy icons like Tina Fey and John Mulaney. O'Brien co-wrote the original Five Timers sketch for Hanks in 1990.
What if Conan O'Brien stayed at Saturday Night Live?
But what if Conan O'Brien did relax and stick around Saturday Night Live? It's not a stretch to say the entire comedy landscape would be different. SNL would have even more iconic sketches, and maybe Lorne Michaels would have turned O'Brien into a cast member.
O'Brien's strengths are as a writer, yes. Yet he did have dreams of being a performer, and we know Lorne Michaels saw enough in him to think he could be in front of the camera every night.
Imagine if instead of leaving, O'Brien was bumped up to a cast member for season 17? He would have starred in sketches alongside Dana Carvey, Phil Hartman, Chris Farley, Adam Sandler, David Spade, and Kevin Nealon
We'd probably never have seen "Marge vs. the Monorail" if O'Brien stayed at Saturday Night Live. One of the signature episode of The Simpsons, O'Brien wrote it in 1993.
And of course, late-night TV would have been on a completely different timeline had O'Brien stayed at SNL. Perhaps one of the other candidates, Jon Stewart, Drew Carey, and Paul Provenza, would have landed the job. That would potentially mean no Daily Show with Jon Stewart and O'Brien likely never getting a shot at his own show.
So in the end, it all worked out for the best. Conan O'Brien is a late-night TV legend, even if didn't have the best of times at Saturday Night Live.