Mr. Smith Gets a Hustler (2002)

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Two men search for an emotional center to their lives and become embroiled in a circle of drugs, prostitution, deception, and blackmail in this independently produced feature. Adapted for the screen by Matt Swan from his off-Broadway play, Mr. Smith Gets a Hustler opens with its titular conceit:… More Two men search for an emotional center to their lives and become embroiled in a circle of drugs, prostitution, deception, and blackmail in this independently produced feature. Adapted for the screen by Matt Swan from his off-Broadway play, Mr. Smith Gets a Hustler opens with its titular conceit: Middle-aged businessman Mr. Smith (Larry Pine) leaves his comfortable suburban home for Manhattan's Lower West Side one night to hire male prostitute Bobby Blue (Alex Feldman). Once they get to the hotel room, however, Bobby is surprised to find that Mr. Smith would rather talk than have sex with him, and the pair continue to meet -- for a fee -- for philosophical conversations about their home lives and futures, or lack thereof. But when Bobby starts forgoing his other tricks in favor of spending time with Mr. Smith, his pimp Lapp (Benjamin Hendrickson) becomes suspicious, and Bobby and Mr. Smith find themselves the focus of an inordinate -- and inordinately dangerous -- amount of scrutiny. ~ Michael Hastings, Rovi