Last week Mitt Romney, the newly ordained GOP front-runner, put his foot in his mouth while meeting with jobless voters in Florida. “I should tell my story,” Romney joshed. “I’m also unemployed.” Well, yes, but according to an AP report from 2007, he and his wife are worth at least $190 million. Oddly, a similar scene plays out in Conan O’Brien Can’t Stop, a new documentary about the late-night comedian’s recent 44-city concert tour. As you may recall, O’Brien inherited The Tonight Show in 2009 when NBC moved Jay Leno into prime time, then lost the show six months later when his and Leno’s dismal ratings forced the network to reverse its decision. Early in the movie O’Brien—who received a settlement of $32 million but had to agree to stay off the air for six months—lounges unshaven on a bed and looks forward to the tour. “You can get out there and talk to people, at least about being unemployed, being legally prohibited from being on television, which is gonna be something I talk about.” Wait, let me get comfortable first.

Rodman Flender, a veteran TV director who followed O’Brien’s road show around the country, makes his theme explicit with the title: O’Brien comes off as a maniacally driven entertainer hungry for the spotlight and unwilling to go home until the last fan has gotten his autograph. In the opening segment Flender sits in the passenger seat as the comedian tools around Los Angeles. “Do you think you could have fun without an audience in front of you?” asks Flender. O’Brien, wearing shades, doesn’t answer and eventually looks over at him as if reconsidering whether this cinema verite project was such a good idea. But this relatively benign showbiz archetype—”Gotta sing! Gotta dance!”—gradually gives way to another one: the beloved entertainer who shows an uglier face backstage. At least in the context of this tour, Conan O’Brien turns out to be a fairly unpleasant man, tense and self-obsessed, endlessly needling and browbeating his staff. Everyone laughs at the boss’s jokes, which are incessant to the point of irritation, but actual levity is in short supply.

O’Brien can’t always have been like this. When he succeeded David Letterman as host of NBC’s Late Night in 1994, he was a 30-year-old unknown, a tall, geeky writer for Saturday Night Live and The Simpsons who had no track record as a performer. In his early shows he was painfully awkward, but eventually his wit and sincerity made him an appealing TV personality. The wit has survived, but the sincerity has long since burned away in the hot glare of the late-night ratings wars; watch his new TBS show Conan and you’ll see a man prancing around like Mick Jagger, climbing on the furniture like Tom Cruise. Last week, saddled with a terminally boring Tom Arnold as his opening guest, O’Brien actually grabbed Arnold and pulled him up to the camera lens for some antic unfunniness. In Conan O’Brien Can’t Stop this rampant egomania finds even bigger stages on which to play out, as the TV star sings and plays guitar with his band, running out into the audience on a ramp like a rock god. Here in town O’Brien sold out the Chicago Theatre.

In the movie, O’Brien and his sidekick Andy Richter deliver a few cracks about Jay Leno, who was glad to take back his late-night slot at NBC and let O’Brien fend for himself. (New York Times reporter Bill Carter chronicles the NBC fracas in his behind-the-scenes book The War for Late Night.) But the Leno-O’Brien dustup seems ironic given how similar the comedians are in temperament. This isn’t a replay of the Leno-Letterman contest for The Tonight Show in 1993, when an affable showbiz climber triumphed over a grouchy, philosophical misfit. Like Leno, Conan O’Brien was a company man at NBC, never less than ingratiating toward his guests no matter how feeble the project they might be plugging. Though he graduated from Harvard, he never pushed Late Night in a cerebral direction the way Jon Stewart and Stephen Colbert have with their late-night programs. O’Brien has always been fretfully concerned with keeping things light, and though his quirky humor can be more interesting than Leno’s meat-and-potatoes sensibility, both comedians trade primarily in showbiz chitchat.

The truth of the matter is that both Leno’s prime-time show and O’Brien’s Tonight Show were weak: NBC affiliates finally revolted against Leno’s low ratings, and O’Brien was losing the late-night battle to Letterman by a million viewers. But as Carter reports, O’Brien placed the blame squarely on Leno. “I know how hard I worked for this,” O’Brien told the NBC executives when they informed him they wanted The Tonight Show back. “It was promised to me. I had a shitty lead-in.” In his concert, the first big stand-up comedy piece enumerates the stages of grief after losing one’s talk show (something we can all identify with). “I’m very angry about the way I was treated,” O’Brien tells Flender. “I’m the least entitled person you will meet in the world. I don’t think I’m entitled to The Tonight Show, I don’t think I’m entitled to success in show business. But sometimes I’m so mad I can’t even breathe.” His anger colors the entire movie, to the point where even his generosity toward his fans seems to be tied up in his professional pique.

At the very least, O’Brien is self-conscious enough to recognize his extreme good fortune in life and satirize it onstage with a parody version of “Polk Salad Annie,” a staple of Elvis Presley’s live act in the 1970s. The Presley version begins with a soliloquy about the title character’s hard life in rural Louisiana, but O’Brien absurdly transposes it to his native Brookline, Massachusetts, where his mother was a successful tax attorney and his father was a microbiologist who did work for the World Health Organization. “Real white trash,” O’Brien observes. Like the Presley rendition, this one climaxes with a hard-boogying rave-up, O’Brien chanting, “My mama shopped at Whole Foods / My daddy had a good job.” Two fine-looking black women—the Coquettes—have been recruited to sing backup for him, and they all do some dancing. Backstage, the singers seem uncomfortable in the bright, smart-alecky touring company, and later in the film O’Brien is irritated when each of them brings a long line of friends and relatives backstage to meet him.

Flender documents the show’s development and rehearsal as well as the performances, and an air of apprehension hangs over the backstage scenes. O’Brien is the sort of boss who makes sarcastic jokes about his own power even as he coldly exercises it. When his assistant gets his lunch order wrong, he quips, “I’m sorry to let you go over this.” Hanging out with his writers, he gets a dumb bit going in which he talks into a banana as if it were a telephone, then bullies his underlings into playing along. “This is very demeaning,” his assistant tells him as he orders her to address the banana. Later he asks another colleague, “Did you talk over me again?” A dressing-room visit from Jack McBrayer (Kenneth the page on NBC’s 30 Rock) turns openly nasty, O’Brien mocking McBrayer’s southern accent and serenading him at the piano: “You stupid hick . . . you were born in shit . . .” What makes all this so unpalatable is the lack of any good humor; O’Brien isn’t trying to make people laugh so much as remind them he’s the top dog. “I’m extremely hard on myself, and sometimes that spills onto other people,” he explains at one point.

The tour, with its endless travel and big, ecstatic crowds, transpires on a scale so much larger than Late Night With Conan O’Brien or even The Tonight Show that it forces O’Brien to reckon with his stardom, and his response is oddly conflicted. He clearly craves applause: despite his growing exhaustion he agrees to spend a day off appearing in a talent show for his class reunion at Harvard, then adds a secret show at Jack White’s studio in Nashville, then agrees to emcee the Bonnaroo Music Festival in Manchester, Tennessee. But even as he drives himself and his staff, he complains constantly about his commitments: he’s annoyed at having to greet so many people backstage, annoyed that journalists want interviews after the shows, annoyed that 60 Minutes is taping his birthday party for a segment about him. After one of his shows at Radio City Music Hall, he ignores his producer’s advice to go home and rest. “You don’t get it!” he says. “I can’t go from this to—doing what? Sitting and reading a Kindle? That’s not gonna fucking happen.” Then he bursts out onto the street to sign autographs, acting annoyed.

Throughout the tour O’Brien makes it a point of pride to oblige his fans, though even this comes off as self-centered. “It feels really good to go out and perform in front of people,” he tells Flender, lying on his back with an expensive Gibson acoustic guitar resting on his chest, “and be in contact with people who are enthusiastic about . . . me, and what I do.” Later, when a middle-aged woman shows up backstage with sugar cookies in his likeness, he repeats the sentiment: “Thank you for liking what I do.” Of course most of these people have paid a pretty penny for their face time; in Chicago, VIP packages were $695. But O’Brien also readily chats with people he bumps into as his tour bus rolls across the U.S. There’s a striking scene at a truck stop in which he encounters a trio of women in a minivan, one of whom tells him how sorry she is that he lost The Tonight Show and asks if he’d like them to pray for him. O’Brien is touched, and he joins hands with the women to pray for his success. At least they’re praying for him, not to him.

E-mail J.R. Jones at