8. Conan O’Brien


The monologue isn’t written and the sketches are nowhere near ready, but Conan O’Brien isn’t worried. Or if he is, he isn’t letting on. There’s none of the mock outrage you see on camera, just mock rudeness. There are no puppet strings attached to his hips, no nipple rubbing. It’s nearly noon on a Tuesday in April, and he’s sitting at his desk on the Warner Bros. lot in Burbank, California, dressed in a brown short-sleeve knit shirt and jeans, sipping a Starbucks coffee and looking over tonight’s comedy rundown: Andy Richter imitating a viral video of a baby sliding down stairs on his stomach. Larry King in the theater’s rafters hosting a call-in show. On paper, the bits sound deliciously silly. Pure Conan. And there are more in the works, more than can fit. Which means that the rundown O’Brien holds in his hands is worthless.


Conan: “Do you want something to drink?”

Me: “Sure, water would be great.”

Conan: “That’s not happening.”

Conan: “He’s a former lawyer, so no one can argue like Mike Sweeney.”

Creating a nightly comedy show like Conan, he says, is like turning carbon into a diamond: “You need an incredible amount of pressure, and as you get closer and closer to the show, the pressure increases.”

O’Brien’s comedy mine is Stage 15, the cavernous soundstage where Blazing Saddles and Ghostbusters were filmed. And where at 4:30 p.m.–in less than five hours–Richter will belt into the mic, “Conan O’Briiiiiien!” Pressure? What pressure? Beneath the desk, O’Brien’s leg is now bouncing like mad.


Monday afternoon: Some comic elements are prepared days ahead of time.

“Larry King in the Rafters” is an idea that has just been awaiting King’s availability. When he learns that King can do Tuesday’s show, Mike Sweeney, O’Brien’s head writer, emails him the script after Monday’s taping. King, perched 30 feet or so above the audience, will interrupt the monologue and take calls as if he’s back on CNN. The only hitch? King can’t (or won’t) make rehearsal. He’ll do the bit for the first time when the show tapes.

Tuesday, around 9:30 a.m.: O’Brien calls Sweeney en route to the office from somewhere on the 110 freeway, and they go over the show. “Sometimes he’ll disagree, then we argue about it,” O’Brien says. Typically, Sweeney arrives an hour before his writing staff to read over scripts.

Today’s show should be fun. Comedic polar opposites Tracy Morgan and Charlyne Yi, the quiet, deadpan darling who wrote the indie film Paper Heart, are on. Adding to the fun is a television first: When Conan airs at 11 p.m. on the East Coast, O’Brien will live-blog on Team Coco’s Facebook page, commenting on the show he spent all day creating. For the King piece, O’Brien suggests introducing him instead of being interrupted. “If we were doing a show that was more controlled, like an SCTV or Kids in the Hall,” O’Brien says, “I would be interrupted. It’s a little more elegant. But in this environment, where we’re doing vaudeville, it might be confusing.” Sweeney sends the new script to King, who’s due to arrive at 3:45, less than an hour before he goes on.

10 a.m.: The writers hit the brown couches in Sweeney’s third-floor office and try to channel the boss’s comic sensibility. “They need to marinate in the essence of Conan,” O’Brien says. With the Tonight Show debacle well behind him, O’Brien is enjoying his fresh start at Conan on TBS. It’s the first show he hasn’t inherited, and he’s creating all-new material. “The thing I keep telling everyone is ‘The only way we can screw this up is to not be bold enough.’ ” The walls in Sweeney’s off ice are covered with index cards scrawled with ideas–some failed, some in need of an ending, some “runners” (i.e., regular bits) waiting to return: Andy has a sidekick. Can Andy nap here? The flaming c, the fishnet-wearing, oven-mitt-wielding superhero created by O’Brien and drawn by legendary animator Bruce Timm.

Conan: “This sounds disgusting.”


O’Brien, one of six kids, likes to wander the halls with his guitar, interrupting writers like a little brother pestering a sibling during homework. “One of my favorite things is to take out my iPhone and pretend to read them reviews of the show, which all praise my ability to rise above the writing,” says O’Brien, who wrote for Saturday Night Live and The Simpsons before crossing over to late-night host. “It’s all a joke. At the very least, I’m trying to create an atmosphere where failure is inevitable and where everybody gets to make fun of everybody.”

A little after 10 a.m.: When O’Brien gets to the office (later than usual–he had a doctor’s appointment), he checks in with Jeff Ross, his longtime executive producer. Their offices are adjacent, separated by a couch strewn with orange Conan pillows. “He tells me the big headline,” O’Brien says. ” ‘We’re being sued by McDonald’s’ or, I don’t know, ‘They’re coming to arrest you.’ “

11 a.m.: At the staff production meeting, the various departments–props, stage, hair and makeup, costume, etc.–coordinate what needs to get done in the next five hours. The writers produce their own pieces, which is how O’Brien learned at SNL. This requires a face-to-face meeting to explain the idea. Otherwise, says Sweeney, “it’s like Spinal Tap: ‘Wait, who thinks we wanted an 18-inch-tall Stonehenge set?’ “

As usual, there’s a lot going on. A photographer is shooting the staff exterminator, played by one of the writers, catching a rat. Someone’s outfitting the Richter dummy for the stairs pratfall. (An earlier option: taping the real Richter throwing himself down the stairs.) And stagehands are constructing King’s talk-show set in the rafters.

Sweeney: “That’d be funny,” without explaining how Richter would survive the stunt.

Noon: O’Brien reads the first round of jokes for the monologue. He rewrites some, checks the ones he likes, puts a squiggle by those that need work, and jots “GA” (for “great area”) by others that need a new take on the same topic. The squiggles and GAs always outnumber the checks.


1:30 p.m.: O’Brien’s jamming the White Stripes’ “Seven Nation Army” on his electric Gibson as if this is last summer’s “The Legally Prohibited From Being Funny on Television Tour.” It’s a typical rehearsal, except that things usually start at 1. (Blame the King set or my interviews. Your call.) Interns and writers sit in the audience, and O’Brien strums around the stage while the crew sets up each sketch. The guitar gets his creative juices f lowing, giving him an outlet for his energy.

Comedy writing has two main ingredients, O’Brien says. Part one: left-brain bullshitting. Part two: seeing ideas up on their feet, in rehearsal, and then reworking them. After writing for TV for 25 years, he still doesn’t know what will translate from paper to stage. But he often knows how to make it funnier. O’Brien leans against the front of his desk–Steve Hollander, the stage manager, calls it “home base”–introducing each bit as though the show were live, and then he watches and listens. After the Richter dummy tummy-surfs the stairs like the toddler in the video, the real Richter emerges on camera as if it were him all along. The smoke on his chest? Richter’s idea. (From the friction, get it?) It doesn’t play. Kill it. “Would it be funnier if he stood up in front, like a dismount?” O’Brien asks. It is. Richter pops up like an Olympic gymnast, punctuating the goofiness. An even bigger laugh: Richter returns to his podium sucking a baby bottle like the kid.

Not everything works, of course. Just last week, “LaBamba Has an Idea” (a tour inside the head of the show’s mercurial trombone player) had so many technical problems, it got pulled. Today, the King sketch needs work. O’Brien suggests different camera angles and close-ups to play up the absurdity. A shot of O’Brien from the rafters. A shot looking up at King. “The messier the better,” O’Brien says. He loses the skyline backdrop to show more beams and pans back to include King’s skinny legs beneath the desk–a shot you never saw on CNN.

Sweeney: “It turned into a mini train wreck. A toy train wreck. No lives were lost.”

2:10 p.m.: During breaks in rehearsal, O’Brien gets busy again on the guitar. “Roll Over Beethoven.” “Revolution.” The show’s band backs him for a rendition of Radiohead’s “Creep,” oddly featuring a saxophone.

Conan’s lyrics: “I don’t think Radiohead has a sax / When you think about it, it’s an extraneous instrument.”


After the interns and most of the crew leave, O’Brien, Richter, and Sweeney gather around the guest couch, draped with a protective covering, and improvise. Richter, a caller from Burbank, phones in to King’s show: “Hey, Larry, have you seen a green Frisbee up there with ‘Andy’ written on it?” Another caller: “Larry, do you really need that other show going on underneath you?”

Wary of “overcooking things,” O’Brien doesn’t rehearse the sketch again. “The biggest comment I get from everybody on this new show is, ‘You look like you’ve having fun,’ ” he says. “You can fake it a little bit, but you can’t fake it day after day.”

2:30 p.m.: O’Brien heads to his dressing room and finalizes the lineup with Ross and other producers. Bits on Twitter insurance and botched surgery get bumped. He wants as much comedy as possible, but he doesn’t want to feel squeezed with the guests, the way he did the day before with Russell Brand. Some guests are an automatic “two,” meaning two segments, broken up by commercial. Without a doubt, Morgan’s a two.

Conan: “Andy Richter comes in, too, just to tell us that it all sucks.”

Conan: “Hey, this is a shitload of ads! How come I’m not seeing any of this coin?”

Around 3 p.m.: O’Brien spends 20 minutes or so with his monologue writers in his dressing room, punching up the material and pitching new ideas from the day’s news. On Charlie Sheen’s attempt to trademark his phrases: “Unfortunately for Charlie, ‘Adonis DNA’ was already trademarked–by my mother on the day I was born.”


Conan: “Finally, someone brave enough to make a Charlie Sheen joke.”

3:30 p.m.: O’Brien enjoys a 15-minute nap/”reset” before the hair-and-makeup staff knock on his door. “It’s that thing Napoleon used to do,” he says. “I have a hard time doing it, because I’m very type A.”

3:45 p.m.: Another meeting with the monologue writers. At this point, O’Brien is trying out the jokes on Ross and Richter and other people backstage, tossing whatever doesn’t get a laugh. On the Jersey Shore kids’ demand for a raise: “The cast says that MTV had better come up with the money, or else they’ll take their lack of talent somewhere else.” A keeper.

3:50 p.m.: King, short, stooped, and wearing a red rain slicker, finally arrives in the green room without a care in the world: “Hey, guys!”

Around 4 p.m.: O’Brien and Richter run lines in the dressing room with King. It’ll have to do.

4:30 p.m.: Richter: “Conan O’Briiiiien!” O’Brien walks out and ignores the jokes on the cue cards for the first minute. He spies a giant of a man in the crowd and improvises. “Look at this guy, he’s a monster,” he says. He brings the 6-foot-9 man on stage and the 6-foot-4 O’Brien hugs him forcefully. “The formula is to prepare like crazy,” O’Brien says. “But then, just as you’re heading out, forget all of it.”


4:39 p.m.: The Richter-dummy fall and dismount go over well. So does O’Brien’s clumsy attempt to kick the dummy offstage. It wasn’t in the script. He added it in rehearsal.

4:41 p.m.: O’Brien: “Live from 30 feet above me, Larry King!” Rehearsal, shmehearsal. Larry King kills. His comic timing is spot-on. When O’Brien comes back from break, he tells the crowd that King had to leave. The camera cuts to King’s desk in the rafters, and Richter’s dummy is filling in. Another unplanned bit that gets a laugh. O’Brien came up with the idea during the commercial.

4:55 p.m.: Morgan, the wild card, doesn’t disappoint, pointing out that his nipples are visible through his fishnet shirt: “As soon as I come on, I start lactating.” He barely mentions the movie he’s ostensibly there to plug. He does one off-color riff after another, and O’Brien gleefully hangs on for dear life. It’s a two, all right.

5:30 p.m.: After the taping, Ross, Sweeney, and O’Brien reconvene in his dressing room to “talk down” the show–what worked and what didn’t. There’s not much to criticize today. The scripted comedy worked, but much of the show was spontaneous. When that happens, “the whole energy in the room changes,” O’Brien says. “People know that these cookies are being made fresh right in front of them, and it’s exciting.”

9 p.m.: O’Brien, joined by Sweeney and a couple of writers in Sweeney’s office, wraps up the Facebook live-blogging marathon, during which they posted 53 jokes in 60 minutes. O’Brien’s final zinger: “We don’t run credits because I do everything myself.” Another day in the comedy mines, another diamond.


In these audio outtakes, Conan tells senior writer Chuck Salter about the process of creating his nightly show. The last video shows the hijinks that ensued during our cover photo shoot, in which Conan portrayed everyone from Einstein to Madonna.




In this exclusive video produced for Fast Company, illustrator John Kascht shows how he captures Conan O’Brien’s essence.



Twitter: @conanobrien