Heeere’s Conan

The first episode of “Late Night With Conan O’Brien” in 1993 opened with a skit where the relatively unknown host strolled to work as people he encountered kept reminding him, “Better be good!” and “Lot of pressure!”

Alone in his dressing room, a whistling O’Brien grabbed a rope and prepared to hang himself – until there’s a knock at his door to tell him it’s show time. Then he bounces out of the room, ready to go on the air.

It was a sly, self-aware beginning for a man who seemed an unlikely replacement for David Letterman, but who went on to defy the naysayers and win over a devoted audience with his unique brand of comedy.

Now comes the biggest step in O’Brien’s television career. On Monday, he’ll become the new host of NBC’s “The Tonight Show,” the job once held by Steve Allen, Jack Paar, Johnny Carson and, until Friday, Jay Leno.

His first guest is Will Ferrell. His old sidekick, Andy Richter, will be his announcer.

As the tall, lanky host (O’Brien’s legs stretch like Mr. Fantastic’s in the promo of him running on the beach to “Eye of the Tiger”) prepares for the move, the questions are mounting.

Will Leno’s move to a five-nights-a-week show at 10 p.m. in the fall eat into O’Brien’s ratings? Can “The Tonight Show” retain its stature in the fragmented media age?

How will O’Brien’s post-midnight humor be received by a more mainstream audience that wants to hear a few jokes about politicians before going to sleep?

Talk about pressure. Lot of pressure.

In January, when O’Brien was in Detroit to visit the local NBC affiliate, WDIV-TV, he sounded calm and confident.

“I don’t want to overthink,” he said. “I don’t want to say, well, this is 11:30, so I better button up and maybe try and have a little less fun and be a little more serious. …

“When I’m having a good time and enjoying myself and doing things I think are funny, it tends to work. I think that’s what I have to continue to do at 11:30.”

That same month, at the annual conference in Los Angeles for TV journalists, he resorted to his usual self-deprecation when fielding a question about taking over the “The Tonight Show” with Leno casting a prime-time shadow.

“Since – what is it? – 1949, 1950, ‘The Tonight Show’ has been 11:30 on NBC. And, to me, that is sacred territory. …

“A few people asked me, ‘Does this, you know, in any way diminish “The Tonight Show”?’ And my response is I don’t need any help diminishing ‘The Tonight Show.’ I’ve got that covered.”

Don’t be fooled into underestimating him. The O’Brien charm has worked for him as an Emmy host, and it’s also a powerful force in person.

At his Motor City stop this winter, “from the moment he walked in, he captivated these people,” recalls Marla Drutz, WDIV’s general manager.

Mary Ann Watson, a professor of electronic media at Eastern Michigan University, counts herself among O’Brien’s fans.

“He’s like the smart kid in the class who’d make sardonic comments, the kid in AP English who would make wisecracks,” she says. “You just know he’s a really smart guy.”

A brief history of O’Brien goes like this: The third of six children, he grew up in Brookline, Mass. A graduate of the Ivy League, he was president of the famous breeding ground for humorists, the Harvard Lampoon. A writer for “The Simpsons” and “Saturday Night Live,” he was plucked from obscurity by Lorne Michaels to fill the NBC spot left vacant by Letterman, who landed at CBS.

O’Brien endured some early bad reviews (years later, at a commencement address at Harvard, he remembered how the Washington Post’s Tom Shales said he should return to “Conan O’Blivion”). But his ability to be uninhibited and goofy, and yet step back and analyze his own weird foolishness, clicked with younger viewers.

He took Letterman’s post-modern attitude to new levels with bits like Triumph the Insult Comic Dog – the puppet that spews harshly accurate insults – and In the Year 2000, where flashlights held underneath the chin and clip-on space collars set the low-budget tone for strange predictions .

“He added a real element of irony and absurdism that hadn’t been in late-night before,” says Ken Tucker, TV critic for Entertainment Weekly, who notes that O’Brien’s strength is “in that space between the monologue and when the guests come on.”

When NBC announced in 2004 that Leno would hand over the “Tonight” throne to O’Brien in 2009, it must have seemed like an easy way to lock in a rising star and guarantee the stability of the network’s late-night future.

But O’Brien is entering a fray he might not have anticipated then.

Leno’s switch to prime-time has changed the equation – and irked Conan followers who see the older comedian as stealing their guy’s thunder.

There’s also the competition from Comedy Central’s 11 p.m. block of “The Daily Show” and “The Colbert Report,” two shows that have evolved into political and social forces.

The most intriguing prospect, however, is that the late-night arena soon will symbolize a triumph of the Letterman comic sensibility.

Both ABC’s late-night host, Jimmy Kimmel, and O’Brien border on reverence in their appreciation for Letterman as the senior statesman of ironic humor.

Can Letterman, who was denied “The Tonight Show” job long ago, now replace Leno as the ratings king? Or will O’Brien keep Leno’s fans, even though his style is closer to Letterman’s?

O’Brien’s June launch is a plus, according to WDIV’s Drutz. Because shows typically debut in the fall – and because late-night viewing tends to go up a bit in the summer – it’s a good time for him to get maximum exposure.

Drutz is convinced his style will fit nicely into his new time slot.

“His humor is such that it’s going to translate easily to an earlier crowd,” she says. “What he’s going to end up doing is expanding his base, so that instead of it maybe being more of a 24-to-35 crowd, it’s going to end up being more like a 25-to-54 kind of crowd.”

Eastern Michigan’s Watson thinks O’Brien will succeed on some level, but she doubts he or anyone else will ever dominate the late-night landscape again.

“I think the days are gone of a Johnny Carson, someone who’s the king of late night. That’s ancient history,” she says.

Maybe O’Brien doesn’t need to worry about comparisons to Carson, Leno or Letterman. Maybe his biggest competition is himself.

“In a way, I feel like Conan’s challenge is to adjust himself for the kind of mass audience that Jay Leno built up,” says Entertainment Weekly’s Tucker. “It’s whether or not Conan can become, in a sense, more mainstream without either alienating his core audience or watering down what he does best.”

Back in January, O’Brien talked fondly about watching “The Tonight Show” with his father as a kid.

“I have an emotional attachment to the show and I think a lot of Americans do,” he said. “To me, it’s a huge responsibility, so my job is to go in there and do the best ‘Tonight Show’ I can do, and every ’Tonight Show’ host has put their own spin on it.”

The smart guy from Harvard knows he’d better be good.