“All of us experience terrible disappointments in our lives and careers,” he says. “We all get jobs and lose jobs but very few of us do it on the front page of the New York Times. So as his friend I wanted to be there for him. However, as a filmmaker I wanted to detach myself. That was difficult for me.”
The pair began to document the creation of O’Brien’s live touring show, a two-hour, all-singing, all-dancing way for the host to thank the fans who stood by him as he was unceremoniously sacked as Jay Leno’s replacement on The Tonight Show.
“I wanted to capture the process of putting this tour together,” says Flender, “to capture Conan at this moment in time, at such a crossroads in his career. To see how the tour evolved and the nuts and bolts of the tour in a kind of Judy Garland-Mickey Rooney, ‘Hey let’s put on a show’ kind of way.
“I never wanted it to be a promotional piece for Conan. I just wanted to capture, in the true, old-school direct cinema style, whatever happened.”
In that spirit the movie reveals an unvarnished portrait of the star.
“People have asked me, ‘Is this the real Conan O’Brien?’ Yes. But so is the guy you see on TV every night. What you see in the movie is the real Conan O’Brien without a script.
“And like a real person, he has real feelings and he has moods and he is kind and generous and he gets tired and cranky at the end of a long day and that is what I think it is to be a human being. It’s interesting to me that so many people have thought, ‘Oh wow, it’s such a negative portrait of him,’ but he doesn’t do drugs, he doesn’t abuse anybody.”
O’Brien’s down-to-earth side is evident in the off-stage footage, particularly in his interactions with fans.
“He really wants to be kind to everybody and really show his appreciation to his fans and everyone who has done so much and stuck by him,” says Flender. “But there is a toll that takes. He is a human being after all. He’s not a machine.”