Three New Documentaries Provide Surprising Insight Into Their Subjects

Bill Cunningham is one of those rare souls who actually does his dream job. Every day, Cunningham roams the streets of New York City, camera in hand, and takes photographs of people who catch his eye because of what they're wearing. In some cases, it's an outrageous ensemble. In others, it's some small detail of the way they got dressed that morning that jogs something in his capacious memory; a series of idiosyncratic fashion decisions emerges as an unheralded trend in the images he compiles for his weekly On the Street photo feature in each Sunday's New York Times. And as director Richard Press' new documentary Bill Cunningham New York (Zeitgeist DVD) shows, turning the camera around on the photographer proves every bit as fascinating as the people he's documented over the past 50 years.

Of course, this shouldn't be surprising. Documentarians figured out at the very dawn of the form that training an unblinking lens on people, ordinary or otherwise, often yields compelling results. That's never more delightfully true than in this polished new film. An erstwhile milliner and fashion writer, Cunningham landed a dream assignment in photographing New Yorkers' personal style, winning fans among fashionistas (Vogue editor Anna Wintour is among the high-powered talking heads here) and documenting the ordinary (and extraordinary) ways people dress that often filter up from the sidewalks to the catwalks. But more than a person who does interesting work, Cunningham himself is a fascinating subject—a man with access to and influence with the highest levels of fashion and New York society who lives like a monk in a Carnegie Hall studio crammed with filing cabinets, who bikes everywhere at all hours in his 80s and refuses any food or drink while working, and who maintains a fierce humility and boundless enthusiasm for what each new day brings. Almost any creative person would kill to have a job like his, but the inspiring Bill Cunningham New York convinces that no one could deserve it more.

Buck (MPI DVD), another new doc, centers on another intriguing man in another rarified profession. Buck Brannaman has been crisscrossing the country for decades now helping people learn how to better handle horses. The end goals, in their most practical terms, are to accustom a colt to having a rider on its back or help horse and rider work better together. But Brannaman's approach involves a deep understanding of horses and finding ways to build their trust (he was among the inspirations for the novel The Horse Whisperer, and served as a consultant on the film adaptation). As director Cindy Meehl's cameras roll, you watch Brannaman get a raw colt following him around like a dog within minutes and marvel at Brannaman and his horse Pet moving together in a way that's closer to dancing than anything else.

Much of Buck's narrative drive centers on the fact that stoic cowpoke Brannaman's empathy was hard-won: He was the victim of brutal child abuse and was eventually sent into foster care, the latter proving his salvation. But the film also documents how his lessons to people about their horses extend to the people themselves. Riders who have spent their lifetimes applying force in the training of animals gush about their expanded understanding of the power of gentle persuasion. And it's not just words; you can see it working. Instead of pulling any punches for touchy-feeling vibe or happy endings, however, Buck also shows that empathy won't solve every problem. You might not be a better rider after you watch it, but you'll probably be a nicer person, if only for a few hours.

Conan O'Brien always seemed like a humble, light-hearted guy during his long career on late-night talk shows, including his own dream job, hosting NBC's The Tonight Show. When he was pushed out of the latter gig in 2010, he was contractually prevented from being on television for six months. So he launched a live show that toured the country and authorized a camera crew to film the whole thing. Why he did either remains somewhat unclear, and Conan O'Brien Can't Stop (Magnolia DVD and Blu-ray) offers no easy answers.

O'Brien won legions of fans with that very humbleness and lightheartedness, and for them watching Can't Stop may be a bit unsettling. Not that O'Brien doesn't seem like a decent guy—he diligently signs autograph after autograph and exhausts himself at meet-and-greets—but director Rodman Flender's camera also captures O'Brien's genuine bitterness (if not his outward anger) and the kind of neediness and drive that compels a man to put himself out like that, onstage or otherwise. While Can't Stop captures snippets of the stage show, it also captures a bit too much of O'Brien badgering his employees or driving a gag into the ground for comfort, not to mention his mounting complaints about the pace of the tour that he himself launched. It was brave of O'Brien to allow this kind of access at what can only be considered a vulnerable moment, and the portrait that emerges certainly shades the goofy public caricature of Team Coco, but it also lets some of the air out of his breezy on-air persona, perhaps for good.