Transamerica

A pre-operative male-to-female transsexual takes an unexpected journey when she learns that she fathered a son, now a teenage runaway hustling on the streets of New York.

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The first film by Duncan Tucker, Transamerica stars Felicity Huffman as a pre-operative transsexual named Bree (whose given name was Stanley). One week before going under the knife, Bree learns that she fathered a boy who is now 17 and is in trouble with the law. Bree would like to ignore this information, but is forced to meet the young man, Toby (played by Kevin Zegers), by her analyst Margaret (Elizabeth Peña), who will not allow the surgery to happen unless Bree meets him and confronts this aspect of her past. Upon meeting, the son believes that Bree is simply a do-gooder. She buys a car and the two road-trip back to her home in Los Angeles, Bree all the while attempting to keep from Toby the truth of the situation.