Todd Levin recounts his time as a writer on The Tonight Show with Conan O’Brien — his first television writing gig of any kind.
After those first adrenaline-fueled months, The Tonight Show entered a more uncertain phase. We were trying to develop a tone and style that was appealing to our larger audience without betraying what we all found funny. And when you have a nightly show to produce, you can’t always take a leisurely step back and address those larger questions—so you end up focusing on things like format and timing. We’d sometimes receive writing assignments from Sweeney that were both highly specific and utterly vague: “We need ideas that require Conan to walk outside the studio, right after the monologue.” “Looking for ideas for Justin Timberlake today—must be golf-related.” There were times, right after reading one of these e-mails or leaving a particularly tense and gloomy rehearsal, that I felt honestly confused about how to write for this show.
As we pressured ourselves to nail the show’s comedic voice, Letterman was pulling ahead of us in the ratings. Then, following the premiere of Jay Leno’s 10 p.m. show, our numbers tumbled again. Even though we had no real understanding of how ratings could affect our work, we sometimes had serious discussions about them in writers’ meetings, the same way 13-year-old boys discuss sex: with great imagination and little authority. If the network was panicking—I saw no signs of it. The show never fit that cliché image of glowering executives in expensive suits standing in the wings with their arms crossed in disapproval. As far as I could tell, they were more concerned that the cast of Celebrity Apprentice was drinking enough Snapple Compassionberry™ Tea on-camera than how hard we were sticking it to the Gosselins on any given night. After all, the Tonight Show franchise was a long-term investment. Carson hosted it for thirty years, Leno for seventeen, and it took him a couple of years (and Hugh Grant’s frugal taste in prostitutes) before he hit his stride. We figured we’d have plenty of time.
Plenty of time indeed. So much for that.