Sandman the Rappin Cowboy is full of conflicting ideals. He lives in the painfully small and rural North Dakota town of Dunn Center... in Dunn County, of course, but longs for Olympia, WA's urban bohemia. He drives a big rig, but dreams of making music for a living. Rap-country music, to be specific. Roll Out Cowboy, like its subject Chris “Sandman” Sands, eschews the dichotomy that exists in the popular imagination between the city and the country, between red and blue states. Sandman's entire being rests on uncomfortably on these dichotomies. Mixing rap and country is only the most superficial wall that Sandman the Rappin Cowboy tries to break down. Though he embodies these contradictions he seems at a loss to articulate them, preferring to hide behind juvenile humor instead. Chris “Sandman” Sand is three-fourths of the way toward being a really compelling figure, but he is perhaps not larger-than-life enough to support a feature length movie.
For a story about a rappin cowboy, Roll Out Cowboy is kind of depressing. Chris Sand didn't choose to move back to Dunn Center; he ran out of money and was forced to. He repeatedly alludes to chronic depression and is slow to admit that he would obviously prefer to move back to his personal hipster mecca, Olympia, WA. He does weird things to his friends. At one point in the movie, Chris sprays bug repellent in one of his friend's eyes. The guy gets pissed, naturally, but rather than apologizing Chris just sort of stands around looking for someone to give him a cue on how to behave.
Roll Out Cowboy fails in the same way that many tour documentaries fail. Touring with a band consists of long stretches of uneventful nothing dotted with moments of brilliance, insanity, and epiphany. Documentary filmmakers are rarely at the right place at the right time with their cameras to capture those moments. What's left is a whole lot of footage of a whole lot of sameness – guys driving on long stretches of flat, barren land making dumb jokes about nothing and waxing philosophic, poorly attended shows at trucker bars in the middle of nowhere, the inevitable scuffles and gripes that emerge between tourmates. It's all pretty standard stuff, and Roll Out Cowboy fares no better or worse in this regard than your average tour doc.
As the tour that this documentary covers occurred during the 2008 election cycle, director Elizabeth Lawrence and editor Elizabeth Ross successfully capture the hope and naivety of the early Obama era. However, Roll Out Cowboy fails to offer any meaningful insight or hindsight into our country's already played out flash-in-the-pan liberal elation. The blind Obama love the nation felt in late summer and fall of '08 is almost embarrassing to watch two years later. Lawrence and Ross don't have anything to say about that, even though it would fit very comfortably with their study of Sandman himself. Just two years ago, in 2008, both our nation and Sandman the Rappin Cowboy sought to reach across boundaries of rural and urban, of red and blue, of rap and country, of old and young, and say something meaningful. There was failure on both counts.
-Ben