Self-deprecating. There, I said it. The one word that is most often used to describe Conan O’Brien is out of the way. Before continuing, I must disclose my undying man love for “the Cone Bone,” as my friend Christie and I refer to him. One of my happiest moments was when I shook the Man’s hand while sitting in the front row of his studio before a taping of Late Night – my fourth time there. Despite some of the lackluster guests I’ve witnessed both live and on TV, it’s Conan’s own brand of humor that keeps drawing me back. I LOL at robot pimps and FedEx popes. Preparation H always feels best when a big-eared dude rubs it on. And is it normal that manatees make me horny? (That’s probably enough to make anyone who’s unfamiliar log off and say a prayer for my soul.)

Raised in Brookline, Mass., Conan was valedictorian of his high school’s 1981 senior class before attending Harvard, where he graduated magna cum laude with a degree in History and Literature. So how does a background often shared by important businessmen, lawyers, and presidents lead a person to late-night television, where bathroom humor entertains the bourgeois and fart jokes wash over the likes of me with the sophistication of a masturbating bear?

While in college, Conan wrote for and served as a two-term president of the Harvard Lampoon, the University’s humor magazine. After graduation, his comedic sensibility lead him to Los Angeles, where he wrote for HBO’s Not Necessarily the News. Eventually, Lorne Michaels hired him onto the writing staff of Saturday Night Live, where he exercised his comedic chops before beginning a two-year stint as writer/producer of The Simpsons. While working on the iconic animated series, Conan penned the popular “Marge vs. the Monorail” episode, along with a few others.

In 1993, David Letterman was leaving his hosting duties of NBC’s Late Night amid controversy over Jay Leno’s announced installation as the new host of The Tonight Show (following Johnny Carson’s retirement), a spot so many thought was being reserved for Letterman. NBC was left with a decision to make, and it was Lorne Michaels who recommended the then-unknown Conan to replace Letterman behind the Late Night desk. The behind-the-scenes writer/producer now found himself in front of the cameras, which drew criticism from some who felt he hadn’t earned his stripes. After all, he was replacing the David Letterman. Though the first couple seasons of Late Night with Conan O’Brien fared poorly in reviews, Conan began to find some comfort on stage. Eventually, a fan base emerged and grew to the point where its size dwarfed the late-night host’s trademark pompadour. (That’s a big pompadour, friends!)

With a few more hosting gigs under his belt at the Primetime Emmy Awards (2002, 2003, 2006), as well as several Writers Guild awards and one Primetime Emmy for Best Writing in a Comedy or Variety Series (2007), Conan ended his 15+ years as host of Late Night on February 20, 2009. Leaving New York behind, the late-night mainstay was primed to move to Los Angeles and accept the challenge of becoming The Tonight Show‘s fifth host. On May 29, 2009, Conan will be Leno’s final guest on the show that he’s hosted for 17 years. (As has been widely publicized, Leno will begin hosting The Jay Leno Show, a new NBC primetime talk show, in September 2009.) When The Tonight Show with Conan O’Brien premieres on June 1, 2009, the funny man will be joined by old pals Andy Richter (former Late Night sidekick) as announcer and Conan’s Late Night band The Max Weinberg 7. Will Ferrell, who appeared on Conan’s final episode of Late Night, will be his first guest.

I admit great sadness when I heard that Conan was leaving New York for far more “plastic” pastures. I miss sitting in his audience and singing with the Max Weinberg 7. (Granted, it didn’t last long, but the microphone was there, the music was playing, and I sang with the band.) My biggest concern when I heard of this new shift in late night television was that NBC might try to tone the Cone Bone down. His antics are usually off-the-wall and his humor might not be widely accepted by an earlier audience. I don’t want a watered-down version of Conan. I want the same personality that got me tuning in every night at 12:37am. My fears were put to rest when Conan freely spoke on his final Late-Night telecast, addressing this very concern. To paraphrase, “I will not grow up,” he said. And then I breathed a sigh of relief.