Conan O'Brien becomes The Tonight Show's fifth host Monday night

Four men.

That’s how many hosts The Tonight Show has had in its storied 55-year history.

Four.

Steve Allen. Jack Paar. Johnny Carson. Jay Leno.

Think about it: Tonight Show hosts change about as often as Supreme Court Justices.

Now you can add a fifth name to that short list — Conan O’Brien.

After a five year wait, the gangly, carrot-topped comic who cut his professional teeth writing for Saturday Night Live and The Simpsons will finally take over the reins Monday night of the most successful late night talk show in television history.

If the 46-year-old former host of Late Night with Conan O’Brien is nervous about the new gig, he certainly doesn’t sound like it on the phone. There’s almost an eerie calm and maturity in O’Brien’s voice as he talks about NBC’s crown jewel and the pivotal role he’ll play in protecting it.

“I feel like a racehorse who was put in the stalls five years ago,” O’Brien says excitedly. “I’m kicking at the sides. Let’s go!”

What the new ‘Tonight Show’ will look like:
We prided ourselves on having a lot of produced comedy (on Late Night). We will probably try to continue that tradition. That’s what I’m comfortable with. We’re moving from one playground to another playground for the first time in 16 years. It’s (also) an opportunity to think of new ideas. It would be a shame to just dust off Late Night and move it to 11:30. I think people would be disappointed if I didn’t reinvent myself to some degree.

Why there’s no riff between Conan and Jay:
There’s no denying the media — and for good reason — likes conflict. It’s a better story. Jay and I have always…personally gotten along really well. He’s been very kind to me about this whole transition. Jay is staying with the network and going to 10 o’clock (and that) has made the transition particularly easy for both of us. He’s happy. I’m happy.

The main difference between himself and Jay:
He has, like, a 220 car collection and I have my Ford Tarus. Jay established himself in comedy as one of the best stand ups of all time. He loves the jokes. That’s probably his first love. I really like jokes, (but) I probably like the ideas (more). That might be the biggest difference between us. I started out the first seven years of my career in rooms ruminating… about what would look funny as a writer. I come from more of the sketch background.

His formula for keeping ‘Tonight’ on top:
My rule is don’t overthink this. The most important job is to think of funny things to do with my writers and enjoy this. When I’m really enjoying myself and being silly or having fun it seems to be good television. I know it’s The Tonight Show and it’s a big responsibility, but man, it would be a shame not to enjoy it. For the first time in my career, I’m performing for people who are fully awake. I’m gonna have to be a little bit more on the ball.

How his ‘Tonight Show’ will stand out from the other two NBC talk shows:
At some point my show is going to have to morph into a detective show. I think four weeks in, (sidekick) Andy Richter and I will be solving crimes. It’s gonna be Murder, She Wrote with a slightly younger demo.

Why what’s funny at 11:30 isn’t much different from what’s funny at 12:30:
I do think that sometimes people act like there’s a tear in the fabric of time and space that separates 11:30 and 12:30. People don’t watch their episode of Lost at the exact time they’re supposed to watch it. DVRs have changed everything. The Internet has changed everything. People are watching things out of sequence all the time.

Why he never writes with ratings in mind:
I never once said I’m going to do X because that’s going to be a huge rating. I always did what I thought would be funny and then good ratings would seem to come from that. I don’t know how to say, ‘You know, what’s really going to do well with women 35-49? If I do a sewing segment?.’

What he misses most about working in New York:
I miss the street culture. When you walk down the street in Los Angeles, people think you’re off your meds. If you’re not in your car, you better be walking right into a restaurant or a club and if you’re not, that means something’s gone wrong in the circuitry of your mind. That takes a little getting used to. I like to ride my bike (in Los Angeles). Twice I’ve gotten on my bike and gone for a ride and cars would drive along with me (and take pictures) the whole time. That never happened in New York. I kept thinking, ‘I’m the best celebrity out right now? Isn’t Johnny Depp on a unicycle somewhere?’

What he wants the new ‘Tonight Show’ set to look like:
The Tonight Show should be elegant. That doesn’t mean I can’t do silly things in that space, but the space itself should be beautiful. It should look as if Steve Allen could materialize or Jack Paar or Johnny Carson or Jay Leno could go into that space and host (the show). I wanted an art deco feel. I’m a jackass, there’s no changing that, but I want the guests to look good on this set. This has to be set where I can interview Will Ferrell but I could also interview the leader of a country.

Andy Richter’s role on the show:
Andy will be my funny friend who’s there with me. It won’t be that much different from his role on the old Late Show. He and I have such a great connection and such a great chemistry. It’s hard to find that in television.

What makes him laugh:
I’m not a snob when it comes to comedy. I’m almost a zealot about not being a comedy snob. When I was a kid, loved The Three Stooges. There was an episode where a bear steals (a convertible) car and…the bear drives down this road and it gets to the end of the road and just as its going out of view, (the bear) puts out its paw to signal a turn. It was one of the funniest things I ever saw. Funny is just funny. I appreciate a Steve Martin piece in The New Yorker, but I also loved it when he put an arrow on his head. There are so many different ways to be funny. The biggest danger in me taking over The Tonight Show is to overthink it. It just has to be a funny show. For the first time in my career, I’m performing for people that are fully awake. I’m gonna have to a little bit more on the ball.

How he might be a slightly different Conan hosting ‘Tonight’:
People, whether they know it or not, alter their behavior slightly when they show up at a party, depending on what kind of party it is. If you walk in a door and everyone’s in a T-shirt and Bermuda shorts and there’s a keg in the middle of the room, you’re going to behave a certain way. If you walk into a party and the men are wearing white evening jackets and the women are wearing gowns, you alter your behavior slightly. I’m grown up. I was 29 years old when I auditioned for Late Night. I just turned 46 and I have two children and I’ve done almost 3,000 hours of broadcasting. Things have happened to me over time. I’ve changed a little bit. And The Tonight Show will probably change me a little more.