Just about 16 years ago, NBC and producer Lorne Michaels took one of the biggest, boldest risks in TV history. And as of 11:35 p.m. Friday, one can say it paid off big time.

That's when Conan O'Brien plays host to his last episode of NBC's "Late Night" on WMAQ Channel 5 as he prepares to move up to "The Tonight Show" June 1.

For more than 15 years, he's been doing the best and most daring comedy in late-night television, so it's easy to forget that he had little performing experience when Michaels named him to replace David Letterman as host of "Late Night" when Letterman jumped to CBS in 1993.

O'Brien was first and foremost a writer. He'd twice been elected president of the Harvard Lampoon - a feat not achieved since comic great Robert Benchley had pulled it off 70 years earlier. Yet, anyone who's ever seen any of Benchley's movie roles knows comic genius in print doesn't translate to being even mildly amusing on stage or screen.

O'Brien had gotten his feet wet performing with pal Jeff Garlin in Chicago during the writers' strike a few years before, and he'd also done some work onstage with the Groundlings comedy troupe in Los Angeles. But mostly he was known as a writer for "Saturday Night Live" and "The Simpsons," where he flashed his promise cracking up his writing-staff colleagues with vamping schtick.

"He can keep a room of seething, self-hating, resentful comedy writers laughing for minutes on end," "Simpsons" creator Matt Groening said with typical ironic aplomb in Bill Carter's 1994 book "The Late Shift."

So after cracking that tough audience, perhaps it was easy to take the "Late Night" stage. At least, O'Brien made it seem so.

He was lucky to catch a couple of early breaks. First, he debuted at the same time Chevy Chase was trying to crack the late-night field. When Chase bombed, it drew most of the critical flak. Expectations were diminished for O'Brien.

He also benefited from his early sidekick, Andy Richter, a likable lunk from the Chicago school of improv, who by the following summer was putting his own stamp on the show through man-on-the-street bits like his reports from Woodstock 25. Richter really set O'Brien at ease by showing him there was a way to be naturally wacky and funny. Their bits driving O'Brien's desk through the outer world, with the help of green-screen TV magic, and later, "In the Year 2000" became running highlights.

When Richter went off in search of lead sitcom stardom, O'Brien wisely decided not to replace him. By then O'Brien didn't need the sidecar to maintain his balance. He was able to keep the audience entertained with his own natural daffiness, whether pulling invisible strings attached to his hips or scaling his desk in the middle of a celebrity interview.

He also benefited from Robert Smigel, who became his show's unseen most valuable player. It was Smigel who gave voice to Triumph the Insult Comic Dog (his reports on the Westminster Dog Show and the debut of "Star Wars Episode 1" were classics), and he usually did the lips for the best "Clutch Cargo"-style interviews, for instance turning Bill Clinton into a party-hearty Yahoo and source of endless laughter.

What really set O'Brien's "Late Night" apart from the competition was the quality of the writing. He knew how to put together a crack writing staff, drawing largely on contacts at the Harvard Lampoon and here in Chicago.

That's what O'Brien will have to draw on as he moves up to "The Tonight Show." Although I do have one more recommendation on how to ease the transition: Bring back Richter as sidekick. That will not only help set O'Brien at ease, but it will unite "Tonight" with its glory days of Johnny Carson and Ed McMahon.

I'm not going to get ahead of myself in addressing how O'Brien will do at 10:35 p.m., and how Jay Leno will do in prime time when he too moves up to a new show launching in the fall. Those columns can wait. Today, let's celebrate Conan O'Brien's 15-year run on "Late Night." He took one of the greatest gambles in TV history and made it seem like genius.

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