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Kevin Kline, Paul Dano, Katie Holmes & John C. Reilly star in this comedy film based on a novel by Jonathan Ames. A failed playwright, Henry Harrison (Kline), develops an odd mentor relationship with Louis Ives (Dano), a troubled, cross-dressing, aspiring writer to whom Henry sublets a room in his New York apartment. Henry teaches Louis the art of being an "extra man," accompanying and entertaining wealthy older women in their fanciful social lives. Along the way, Louis encounters an environmentally conscious co-worker, Mary Powell (Holmes), and a jealous, eccentric neighbor, Gershon (Reilly).