Bree (Felicity Huffman) lives in the slums of Los Angeles and makes a living waitressing and telemarketing from home. He is a man who is excited about his upcoming gender correction surgery. But when his therapist (Elizabeth Pena) hears that he has a son from the one sexual encounter he had with a woman seventeen years ago, she advises that he should take care of this old business before going ahead with the operation.
Bree flies out to New York where his son Toby (Kevin Zegers) is in jail for possession of drugs and an act of theft. Bree bails his son out, but instead of telling the boy that he's his father, he pretends to be a woman, and poses as a Christian who wants to reform the young man.
When Toby tells Bree that he wants to be an actor they decide to drive to Los Angeles. In the back of his mind, Bree wants to stop in Kentucky where Toby was raised by his step-father — hoping to leave the boy with him. But when she meets him, it turns out that he regularly abused Toby sexually. So much for that option.
Transamerica marks the debut of writer and director Duncan Tucker, who is very interested in the quest motif of road movies. Both Bree and Toby have struggled hard to become independent human beings but they have been impeded by others. They share a bond of being outsiders, never simply accepted for who they are.
On the road, Bree winces at sleeping out doors under the stars, and there are troubles involving the car and money. Bree tries to improve Toby's English and to educate him about the land they are passing through. She has her finest moments on the trip when they are taken in by a kindly Native American (Graham Greene) who develops a crush on her.
The turning point comes when they arrive in Arizona at Bree's childhood home. Her mother (Fionnula Flanagan) is stunned that her son has become such a freak: "We love you," she says, "but we just don't respect you." By this point in the drama, Toby has discovered that Bree is a man — but is less upset about that than the fact that Bree lied about it. The sparks fly in this suburban household, and Bree's mother complicates matters by wanting Toby to stay with them: she is determined to replace the son she lost with this new grandson.
Felicity Huffman puts in a stellar performance as Bree that has already been heralded with an Independent Spirit nomination in the category of Best Actress. It is well deserved.
