Transamerica is one of those movies that feel like it is trying to push an agenda more than tell a story. There is nothing wrong with that, but the story in question is a bit too light to sustain itself, and slowly begins to feel like a sitcom involving a dysfunctional family. A very dysfunctional family. The real reason to watch Transamerica is for the gender-bending performance of Felicity Huffman. Huffman (Christmas with the Kranks, Raising Helen) just won an Emmy for Desperate Housewives and a Golden Globe for her role here. The awards are both well deserved and completely opposite. Huffman proves her mettle by doing well in both, especially here as Bree, a pre-op transsexual. With a lot of makeup, Huffman attains a weird, androgynous look about her. She could be a woman, but could also pass for a man in drag.

Bree grew up a man, but always felt like a woman. She has been on hormone therapy and has breasts. She practices speech therapy in order to make her voice more feminine. Bree is nearing her final surgery, which will remove her penis, and is almost desperate that it happen. It is at this point that Bree receives a call from a young man claiming to be Stanley Osbourne's son. Stanley was Bree's birth name. When she tells her therapist Margaret (Elizabeth Pena, Sueno, The Incredibles) about the call, Margaret puts the operation on hold. She doesn't want Bree to throw away a part of her old life without exploring it.

Bree makes the trip from California to New York to bail out young Toby (Kevin Zegers, Dawn of the Dead, Wrong Turn). She does not reveal her identity, and instead claims to be from a Christian ministry. Toby's life isn't going anywhere. He deals drugs, prostitutes himself, and aspires to move to California to direct porn movies. Bree is not sure what to do about the entire situation, and Huffman is good at presenting her mixed emotions. On one hand, she clearly sees that Toby is a wreck, and could possibly use some parental guidance. On the other, she wants to put her life behind her and move on to a new life as a biological woman. Reluctantly, she offers Toby a ride to California, starting an uncomfortable road trip across America, where both players have the opportunity to examine themselves.