The title Transamerica has double meanings. The film is essentially a buddy road trip. It is also about a transsexual named Bree. The result is an interesting mix of characters study and absurd plot twists.
Bree Osbourne (Huffman) is a pre-operative male-to-female transsexual who is about to get her gender reassignment operation in a week. Unexpectedly, she learns that she has a 17 year old son, Toby (Zegers), the result of a drunken night with a college girlfriend. 
Worse, Toby is a street hustler and a junkie. Bree would have nothing to do with him; however, her therapist, Margaret (Pena), won’t sign the consent form unless Bree deals with the situation. Bree flies to New York to bail Toby out, then decides to embark on a cross-country trip back to Los Angeles with him. The story unfolds as Bree and Toby get to know each other, while they both have secrets they would never want the other person to know.
Huffman (Desperate Housewives) is the heart and soul of the film. Her performance as a transsexual is brilliant. With the help of makeup that turns the sexy actress homely and mannish, she transforms herself into a man who is not at all comfortable in his own skin (or with a penis). Huffman makes us believe in the character with her wit, humor and humanity. She’s inspirational. Zegers (The Hollow) is also excellent as Toby. He shows good control of his character’s external cockiness and confidence as well as his internal insecurity, vulnerability and loneliness. The talented young actor holds his own just fine against Huffman’s beautiful performance. They share great on-scream chemistry.
The supporting cast is good, too. Flanagan (Mad About Dog) turns a caricature into an interesting character as Bree’s religious mother. Young (Land of Plenty) is amiable as her husband Murray. Preston (The Stepford Wives) is loopy as Bree’s sister Sydney. Greene (The Green Mile) is solid as Calvin, a kind American Indian who has the eye for Bree. Pena (The Incredibles) is lovely as Bree’s therapist.
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