Stupid Questions

Stupid Questions with Conan O'Brien

The ''Late Night'' host reveals his secret plans for the 58th annual Emmy Awards, explains how he saved Martha Stewart's life, and reflects on that run-in with Rosie

Conan O'Brien normally helps millions of heavy-lidded people giggle away the wee hours. But on Aug. 27, the host of NBC's Late Night goes prime-time to emcee the 58th annual Emmy Awards (NBC, 8 p.m.). There's only one way to honor the occasion: Give him a golden goblet from which he can sip the blood of his peers. Unfortunately, Jimmy Kimmel swiped it. We hope he enjoys these Stupid Questions instead.

Congrats on re-hosting the Emmys. What went so wrong in 2002 that you have come back to fix it? I thought the comedy went pretty well last time — physically I was a wreck. I've been told I have body dysmorphia, but thin is in, so what I'm going to unveil on the Emmys is the new 111-lb. Conan. And instead of a tuxedo, I'm wearing that outfit that 1950s fitness guru Jack LaLanne has worn for his entire career — a black clingy bodysuit that will accentuate my new V torso and slimmer legs.

What's your strategy this time: Twice as nice or...just phone it in? I'm going to pull a massive all-nighter the night before and then try to do bits with circus animals that I have no experience working with. I think people would enjoy watching the Emmys if the host could potentially be killed, like if my arm was torn off halfway through the show by a cheetah.

There has been some controversy this year about the nomination process. How would you change the rules to ensure fairness, or at least so that you get to take a home a wheelbarrow full of statues? I think the awards should go to the Irish — and I'm not including Denis Leary. I've looked into it and he's French. It's all an act... Every group likes to claim that they've been wronged, but the Irish have suffered terrible degradation and humiliation for years, and I feel we still haven't been compensated. Native Americans get to have casinos, and I think we should get Emmys.

Some hit shows like Lost and Desperate Housewives were snubbed this year. Can you make up some awards for them so they don't feel too bad? I'm backstage much of the time, and there's a large table of Emmys back there, but nobody's really guarding them. This is frontier justice — I'm just handing out Emmys to people who I think deserve them. Hugh Laurie, I've told him to meet me in the parking lot behind the Shrine Auditorium and I'm giving him — it'll say Technical Emmy for Lighting, but he can get another nameplate. And who can stop me? I suppose the Academy, or anybody with a little bit of muscle mass. Or even a particularly tall girl.

If Late Night with Conan O'Brien loses to The Daily Show yet again, will you sic the Masturbating Bear on Jon Stewart when he steps onstage? I've sent him over to The Daily Show several times, but the bear spends so much time masturbating outside The Daily Show offices that there's plenty of time to evacuate Stewart and the staff — and to have the bear arrested. That's the problem, he's not task-focused.

Ever considered switching to the Outstanding Children's Program category to ensure victory? Then again, I hear that Classical Baby 2 is going to be tough competition this year. Classical Baby 2 has some of the best gag writers in the business, plus they tackle social issues. And whenever a children's show tackles a social issue, forget it. They can do the whole isn't-it-tragic-that-I'm-one-and-a-half-and-I'm-still-in-diapers show. There's no way you can win. It's bullshit.... Host Whose Hair Most Resembles a Belgian Pastry — that's the one I'm taking home.

Okay, I'm turning off my tape recorder. What's the secret of your hair? Let's see... One part mayonnaise. Two parts spackling compound. And one part crystal meth. Don't ask me about the last part, but it's very important.

When you're not sleeping contentedly with the Emmy you won in 1989 as an SNL writer, where do you keep it? I had the statue mounted on the handlebars of a girl's bicycle with sparkles and a banana seat, and I ride it around, ding the bell, and shout, ''Emmy coming through!'' Man, the looks of hatred you get are incredible. The last time I did it, I saw Doris Roberts riding a similar bike and she had six Emmys stapled to hers.

What do you consider a greater accomplishment: Earning 14 Emmy nominations for Late Night with Conan O'Brien or persuading Martha Stewart to eat a Taco Bell burrito and drink a 40 on the show? That's obvious — the Martha Stewart moment got me the Peabody Award. I mean, they didn't actually hand it to me, I had to go and take it, but if they're not going to lock their offices, it's not my problem... Shortly after that moment, she ended up in prison, and I gave her the street cred that may have kept her alive in a white-collar prison in Connecticut.

When a guest is all blathery and boring, what goes on in your brain? I always picture one of those high-powered drills that can go through molybdenum steel like butter grinding through their head and then coming out through the bottom of their jaw. But I found when I double up on the medication, it goes away.

You used to live in a Manhattan apartment building that Rosie O'Donnell and Cyndi Lauper also called home. Superawesome good times or awkward elevator passings? Definitely awkward elevator moments. There was a special celebrity elevator in the building that only they could take and I tried to get on it once and Rosie shoved me out the door and said, ''A few more years on the air, pal!'' So I had my own escalator built. Unfortunately it was outside the building and in February and March, I was often treated for hypothermia.

You traveled to Finland this year to meet with President Tarja Halonen, who bears a striking resemblance to you. If you were made ruler of an inconsequential Scandinavian country, how would you exploit your powers? First, I would immediately attack my neighbors on all sides, ignoring the fact that my troops' weaponry is predominantly made of dark, rich chocolate. And I would have anybody with a healthy tan deported from the country so that by contrast I would appear swarthy. People would say, ''Hey, George Hamilton!''

What's the meanest thing that Triumph the Insult Comic Dog ever said to you backstage? ''You're a better puppet than I am.''

Who would play you in the Late Night straight-to-video film? Donnie Most is my first choice. Carrot Top, if they could paint real eyebrows onto him. Maybe the adult Haley Joel Osment in an orange fright wig.

NBC announced in 2004 that you'd be taking over as host of The Tonight Show...in 2009. I'd really love the exclusive: What are your plans for 2029? Television will have changed dramatically by then. Last Call With Carson Daly will be a pill that you place under your tongue, and Deal or No Deal will be a saline solution that you place in the eye... I'll say, ''Good night, everybody — stay tuned for Late Night With Amanda Bynes, I'm out of here!'' and then I'll jump into the arms of a jewel-encrusted robot who will then fly through an opening in the ceiling to my mountain lair, where, grinchlike, I will plan the next evening's entertainment.

Originally posted Aug 17, 2006 Published in issue #893 Aug 25, 2006 Order article reprints