Since moving from the writer's desk to the front of the camera, he has stumbled out of the gate with every job.
Once Conan O'Brien gets his legs under him and finds that sweet spot, it's like leaving a stuffy room to find fresh oxygen.
Conan's career has been fast, unpredictable, glorious and a little heartbreaking. His brand of comedy is a blend of old David Letterman and Saturday-Night-Live-styled skits, but he has managed – with his quirkiness and self-deprecating shtick – to put his own stamp on late night.
His gyrations and his array of childlike falsetto voices usually seem silly to that skeptical and occasional late-night viewer flipping through channels.
It's true some don't get him, but those who have had the patience to come back night after night have been rewarded in waves.
The summer between my high school graduation and first year of college included many nights watching Conan. It was his first year hosting the "Late Show" on NBC. Nothing else was on the tube at that late hour and that was a good thing for the newbie, who was put in a seemingly impossible situation – replacing Letterman, the hip, mad genius who invented a new style for a new late-night time block.
With nothing out there threatening to best him in the ratings, Conan and his writers had time to make the show jell. It became clear they needed it.
Some of those shows were tough to watch. The bits were arcane at best. The audience members laughed mostly because they were anxious to do so. The host's ad libs never seemed to help. Occasionally a quick-witted guest would save the show, but that mostly didn't happen.
Conan was as good as fired. Had NBC nailed down a deal with the likes of Gary Shandling and if Chevy Chase hadn't bombed so infamously with his own late-night show, Conan would've gone the way of Pat Sajak – without a brand like "Wheel of Fortune" on which to land safely.
I spent the next school year at a military college. No privileges were allowed – including television, especially not after midnight. I never was able to track the progress Conan was making.
When I hung out with my friend again the following summer, we turned the channel to NBC, hoping to see a better product.
On one particular night, Conan and his sidekick, Andy Richter, had introduced a new bit – "Conan and Andy at the Movies." They did a mock review, pointed out something they didn't like, followed it with a clip and inserted something zany into it that would justify their critique.
My friend and I watched a few of them and chuckled. Then came the dynamite.
They reviewed the Gene Hackman and Denzel Washington hit "Crimson Tide" and said they were irritated by one particular scene – an introduction of a character who seemed out of place.
When Washington's character relieved Hackman's character of his command, the latter turned and yelled, "Mr. Cobb, arrest this man!"
The screen turned to a man wearing a corn on the cob suit with a shocked expression on his face. It was the cheapest, dumbest and most hilarious suit I ever saw.
"What are you waiting for?" Hackman screamed. The man in the suit threw his clipboard in the air and ran around in a circle.
My friend and I were wheezing for about five minutes. I'm not sure I've seen him laugh harder and vice versa.
Since then, Conan has never stopped making me laugh. After several years of leading in the ratings at the 12:30 a.m. hour, he could have accepted millions to go to Fox for his own show at 11 p.m., but settled for a salary about one-tenth of that amount to stay with NBC (seriously) so he could take over "The Tonight Show" in five years. He wanted Johnny Carson's chair.
He still could've had it even somewhere down the line if he had bolted for Fox, but loyalty won out. Thankful to the network that made him, he didn't want to leave NBC.
When it finally debuted in 2010, "The Tonight Show with Conan O'Brien" wasn't smooth. Conan had high points for sure, but he had many adjustments to make – and his network didn't give him time. Any small change can throw off a host's rhythm. He had to get reacquainted with Richter. He was further away from his band and the audience. He was resistant to step outside of his comfort zone – particularly when it came to booking guests.
His younger audience mostly stayed with Conan, but older viewers left over from the previous host jumped to something else.
I can't sum up the whole perennial-liar-Jay-Leno-bombs-at-10-only-to-stab-his-significantly more-talented-successor-in-the-back situation in a few paragraphs. Others from Bill Carter to Howard Stern have reported or ranted better about it.
Following his forced resignation, Conan quickly found a new home. He has spent the last 13 months at TBS. He's struggling with some of the same adjustments from his criminally brief "Tonight Show" stint and his audience numbers have tapered off since his premiere.
The Wall Street Journal published a story a few months ago inferring there was doubt Conan could enjoy a long marriage with TBS. He was, after all, lagging behind in the ratings to not only Leno and Letterman, but also to a few others on basic cable.
He's being paid a lot of money and with that comes the appropriate demand for results. It also should be noted TBS demoted and eventually shoved out George Lopez after it landed Conan. It was a cut-throat decision that might have dulled some of Conan's luster in the eyes of some.
In time, if TBS is patient enough, the smart money is still on Conan. He's showing a knack for more than just telling jokes (actually his monologue still hasn't soared). His skits – which he had to reinvent from scratch because NBC held on to its "intellectual property" – are snappy and funny and getting better. His "remotes," which are skits outside the studio, constantly elicit big laughs. Most of his band members are still around. He and Richter are reacquiring their chemistry from the late 1990s.
Conan also knows the viral game. He's miles ahead of everyone else in the Facebook and Twitter world. His interviews with the likes of Zach Galifianakis and Tom Selleck were classic and he's unafraid to break the decades-old boundaries of late night.
Conan's last appearance on the "Tonight Show" was exemplary – and it goes a long way to show the kind of person he is underneath the goofy exterior.
Among those he thanked was NBC – for the opportunities it gave him for 20 years (including his early years as an SNL writer). He fulfilled a comic's dream when he hosted "The Tonight Show" for those seven months. He said he had no regrets. He got to do the show his way.
"All I ask of you is one thing – please don't be cynical," Conan told his audience. "I hate cynicism. It's my least favorite quality and it doesn't lead anywhere.
"Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you're kind, amazing things will happen."
Conan still averages more than 1 million viewers per night for a network that rarely sees such numbers. Add that to the fact he's a humble guy incapable of bitterness or mean-spiritedness in spite of every effort by NBC to inject those negative emotions into him.
TBS must know what it has in Conan. I hope so. People like him are in short supply. He needs to stick around.

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