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66 Metascore. A transgender woman takes an unexpected journey when she learns that she mothered a son, now a teenage runaway hustling on the streets of New York. Director: Duncan Tucker | Stars: Felicity Huffman, Kevin Zegers, Fionnula Flanagan, Andrea James. Votes: 41,350 | Gross: $9.02M. 10. Cross-Dressing Movies. 1. Some Like It Hot (1959) After two male musicians witness a mob hit, they flee the state in an all-female band disguised as women, but further complications set in. 2. Tootsie (1982) Michael Dorsey, an unsuccessful actor, disguises himself as a woman in order to get a role on a trashy hospital soap. 3.

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