When, at rehearsal, a piece of comedy was too tasteless, too Late Night, or just too poorly conceived, Conan would let its silent reception permeate the room for a minute. Then he would slowly swivel his head around to meet his writing staff in the eyes and, with grim determination, declare, "I want names." He was joking, but there was a certain notoriety that came with being on the receiving end of one of those. I definitely had my share, like the time I spent an entire day working on two horribly misguided pretaped sketches: one featuring a robot caught masturbating, and another featuring the president's dog repealing the No Child Left Behind Act. Separately they were, as Conan and Sweeney might say, "thin soup." After a back-to-back screening, the response was so deafeningly silent, I felt I owed everyone a handwritten note of apology.

It was always obvious when an idea worked—laughter was usually a clue, though not always—and there were so many ways for one to go wrong. Most of the comedy we created for the show had a very compressed production cycle. It required split-second decision-making and assistance from a number of different departments that were fielding requests from the other writers while also struggling to keep up with a few side projects, such as designing a new logo for Max Weinberg's drumhead. An idea might be conceived at 9:30 a.m., pitched in the head writer's office at 10 a.m., debated and tweaked by the other writers, then approved for that day's show at 10:30 a.m. Between that time and a 1:30 p.m. rehearsal, the idea had to be cast, scored, shot, and edited. Graphics, props, video clips, and sound effects had to be requested, if needed. And, oh yes—there's the small matter of writing the script. That's why a large writing staff was both necessary and extremely humane; it provided breathing room for a writer to have a bad day. To work in that kind of environment without ever falling behind or questioning your self-worth, you would have to be a sociopath.

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 ecutives 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.