I have been a fan since day 1. Just by chance, I happened to be home sick from school when David Letterman’s short-lived daytime talk show debuted. I was in 4th grade and loving every minute of the comedy boom that began in the 1970s: Steve Martin, Saturday Night Live, Andy Kaufmann, Robin Williams were all big influences. I had all of their albums and knew them by heart.

Then came David Letterman. I had seen him on The Tonight Show Starring Johnny Carson. He was fine. He had some good lines. He seemed more in the mold of David Steinbrenner, funny, personable, but not particularly dynamic.

It turns out the monologue wasn’t his greatest strength. Dave was a concept artist. Late Night with David Letterman broke all conventions. Years of Jack Paar, Merv Griffin, Dinah Shore, and Mike Douglas and the has-been celebrity gabfests were held up to a mirror. What Letterman lacked in star power, he made up for in irony, absurdity, and creativity. Jimmy Fallon has done a tremendous job breathing new life into The Tonight Show. But it’s completely scripted and publicist approved. Letterman was raw. Its beauty was in its imperfections.

I don’t have to tell you what happened. Leno got the Tonight Show. Letterman went to CBS and became America’s Darling until he hosted the Oscars in 1995. It wasn’t the greatest hosting job, but I’ve seen Whoopi, Ellen (the first time), James Franco, and others do much worse jobs hosting with no career repercussions whatsoever. Suddenly, David Letterman was no longer above criticism. I believe he gave up that day. Jay Leno booked Hugh Grant fresh off of his hooker scandal and the rest is history. Dave never recovered. Even his return after open heart surgery, didn’t cause the public to fall back in love with The Late Show.

Dave has struggled. Comedy bits that Letterman would have mocked in the past, now make the air. He lost his inspiration. His staff of writers and producers are also to blame. It makes me frustrated and sad.

I was there live for Dave’s saddest moment of all. October 1, 2009: the night he confessed his affair.

It was bizarre. First you need to know David Letterman is notoriously paranoid. His studio is notoriously cold because Dave worries people are going to fall asleep during his show. While waiting in four different lines to enter the Ed Sullivan Theater interns and producers cheerlead you into laughing, “Okay, when Dave tells a joke, laugh as hard as you can, even if it’s only a little funny.” You are literally cajoled into laughing at everything for the hour before the show tapes.

Ushered into the theater and coaxed to clap feverishly as The Black Eyed Peas’ “I’ve Got A Feelin'” blared over the speakers, our seats were fourth row center.

Before the show, Dave comes out to warm up the audience. His staff obviously gives him a report on the crowd. He tried to set the narrative by saying he heard there were a lot of foreigners in the audience. Then he took questions. My hand shot up like a bullet. He picked me. David Letterman called on me. Admittedly, he seemed disappointed that I was American and spoke English, an opportunity for comedy missed. My question to Dave, “What’s the highlight of your television career?” He paused, scratched his chin and said, “Talking to you now, Jim!” There it is. I, Jim Valley, according to the man himself, am the highlight of David Letterman’s career.

Then Letterman started his now-infamous confession. The audience, which had been coached to laugh at anything that might be even the slightest bit funny, made it more awkward by laughing at inappropriate moments. It took several minutes for me to realize exactly what was happening: I was witnessing a childhood hero in the most vulnerable moment of his life. It started like a typical, meandering Letterman story and ended as a baring of his most humiliating secret. To his credit, he didn’t blame anyone but himself. He took full responsibility. That said, what he did was selfish and hurt a lot of people.

During the commercial break, the lights went down and a few staffers gathered around his chair, presumably for support. After a minute or so, Dave got up and exited the stage to his left. Through an open door I could see him pacing back and forth. He quietly returned to his desk and the show went on with guests Woody Harrellson and Kim Kardashian.

Exiting the theater, upbeat and laughing, it didn’t seem that the audience fully grasped what they had just seen. I did. I called my media friends. Nobody understood until it aired. The next morning I did countless interviews for Fox News, Seattle, Spokane, Washington DC (I got to talk to Gopher from The Love Boat!) , and magazines.

I wasn’t there for the velcro or Alka Seltzer suit, throwing Pumpkins off the roof, Larry “Bud” Melman, or Andy Kaufman, but I was there for his worst night and, according to David Letterman himself, the highlight of his career.