End of an Error: As Conan O’Brien Wraps Up 28 Years of Late Night, I Was an Idiot to Leave the Show

What I Learned From Working On Conan’s Season #2 and My Own Fears

Actor John Lithgow playfully tossed a show at me, boxer Larry Holmes jokingly (I think) threatened to knock me out and actress Jennifer Tilly might have flirted with me over the phone until she realized I was just an intern and not a Segment Producer. Memories like those, plus a dressing room sign with my name on it, were what I took away from interning on Season Two of Late Night with Conan O’Brien while in college. And looking back, I never should have left the show.

Conan bid farewell to late night TV this week after an amazing 28 year run, an incredible milestone by anyone’s measure, but especially impressive given where he started: a talented writer but minimal on-screen experience. When I joined, Late Night aired at 12:30am and was still on quarterly renewal cycles, meaning that NBC hadn’t yet even decided to give Conan (and his team) the stability of an annual commitment. Despite his rawness two things were clear: (a) Conan is wicked smart and (b) they assembled a team of new voices who were willing to take risks and commit to the mission of the show. Sounds like a startup, no?

So what was I doing as part of this group? Primarily researching upcoming celebrity guests and drafting potentially interesting interview questions. If they’d been on the show before I rewatched the previous appearances to note stories they’d already told and/or callbacks/running gags that could be revisited. And every once in a while I fact-checked monologue jokes or ran across NYC to pick up celebrity-related props (the vintage denim jacket photoshoot they appeared in pre-stardom, the Japan-only release of a terrible movie they’d try to bury) — you have to remember this was 1994–95 and the consumer internet was still largely in its formative stages.

My time on Conan meant that I spent much of my senior year at Vassar off-campus in NYC, crashing with family and friends, or taking early morning and late night trains to/from Poughkeepsie. My senior thesis on America’s first national women’s magazine filled the other available hours, especially since the primary research could only be done in the…