When NBC shoved Conan O’Brien out of the way to make room for Jay Leno—first by undermining his Tonight Show debut by slotting Leno at 10 p.m., then by more or less giving Leno his old hosting job back when that experiment failed—O’Brien got screwed. Or at least he got screwed insofar as a widely adored multimillionaire entertainer in the middle of a terrible recession can be. “I’m the least-entitled person you’ll meet in the world,” he claims in Conan O’Brien Can’t Stop, a behind-the-scenes documentary about the 44-date, 33-city “Legally Prohibited From Being Funny On Television” tour he embarked upon between his exit from The Tonight Show and his debut on TBS. And while “entitled” might not be the right word, exactly, “aggrieved” would certainly be a fair way to describe O’Brien’s mood on the tour, which was fueled in no small part by his anger over losing the plum late-night gig he spent 16 years earning.
O’Brien’s ouster doubled as his greatest cultural moment: A passionate, creative fan base rallied behind him, the acrid monologues during his last week on The Tonight Show made for event television, and the “don’t be cynical” speech that closed out his final show was one for the ages. That cultural moment had passed by the time the “Legally Prohibited” tour started, yet by the evidence in this documentary, O’Brien’s bitterness carried over into a show that was ostensibly about turning the page. In this sloppy assemblage of backstage and rehearsal footage (and other odds and ends from the road), a secret theme is how the ugly side of show business—the egotism, the rancor, and yes, the entitlement—can consume even the most decent, generous stars.
More for-fans-only DVD extra than movie, Conan O’Brien Can’t Stop doesn’t have any discernable point of view about O’Brien and the tour, other than noting his compulsive need to perform, even on his days off. Unlike most entertainers, he can’t bring himself to turn down any requests for autographs, industry-party appearances, or backstage meet-and-greets, and his accommodating nature takes a toll. While there are more than a few flashes of O’Brien’s joyous eccentricity onstage—his appearance in a skin-tight replica of the leather outfit from Eddie Murphy Raw is particularly inspired—the overall mood of Conan O’Brien Can’t Stop is curdled and sour. It leaves the feeling that the next chapter can’t come soon enough.