Have You Seen Clem (2003)

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A semi-documentary blend of comedy and drama that fuses semi-improvised staged scenes with man-on-the-street footage, Have You Seen Clem follows the adventures of Jaymo (Kris Jamieson), a half-bright skateboarder who suddenly finds himself living on the mean streets of Portland, OR. Having gained a new perspective of the issues of the homeless, Jaymo picks up his video camera and starts making a documentary about the city's street people. One person who especially fascinates him is middle-aged Clem (Clem Weredail), who spends his days collecting bottles and cans and muttering to himself. Jaymo's attempts to get an interview with Clem fail until he discovers Clem's secret -- he's not really a street person, but the founder of a successful fast-food franchise who was cheated out of his share of the profits by a duplicitous businessman. Assuming the identity of a bum while he plots his revenge, Clem makes a deal with Jaymo -- he'll let the skater tag along with him as he makes his way to Nashville to confront his nemesis, keeping up his facade as Clem both to disguise his identity and allow him to blend in with the homeless people they meet for the sake of Jaymo's movie.