Transamerica

The movie is marked by an Academy Award-nominated and Golden Globe-winning performance by Huffman, who is also known for her Emmy Award-winning performance in Desperate Housewives.

Taglines: Life is more than the sum of its parts and Life is a journey. Bring an open mind.

Plot

One week before her vaginoplasty, Sabrina 'Bree' Osbourne (Felicity Huffman) receives a phone call from Toby Wilkins (Kevin Zegers), a 17-year old boy who is jailed in New York City. He asks for Stanley Schupak (Bree's former name), claiming to be his son.

Bree was previously unaware she had a son; she now wants to break with his past and renounce him. She argues that with her son's age he can take care of himself. However, Bree's therapist (Elizabeth Peña) refuses permission for her operation if she does not face up to her past.

Bree flies from Los Angeles to New York to bail Toby out of jail. Toby is a small-time drug user and male hustler with both men and women. His mother committed suicide, after which he was raised by his stepfather, whom he does not want to see again.

Bree pretends to be a Christian missionary but still believes in God, and persuades Toby to ride with her back to the West Coast, secretly planning to leave him at his stepfather's along the way. When they arrive in Kentucky it turns out that Toby's stepfather molested him as a child, and so this plan fails. Toby and Bree continue to Los Angeles together. They also stop by a house where a group of transsexuals are hosting a gender pride gathering. During the trip, Toby accidentally discovers that Bree is transsexual. He is open-minded about it, but is angry that Bree had not told him.

After their car and money are stolen by a "peyote shaman" hitchhiker (Grant Monohon), Toby helps out by making some money by means of prostitution which he had been doing back in New York, finding a truck driver for a client. To Bree he pretends that he got the money from selling some drugs he had taken along for his own use. They get a ride with a kindly rancher Calvin Many Goats (Graham Greene) to Bree's parents' house in Phoenix, Arizona. Here they find her very Christian mother Elizabeth (Fionnula Flanagan), her Jewish father Murray (Burt Young), and her rebellious and sarcastic sister Sydney (Carrie Preston). Elizabeth is very negative about Bree's transsexuality, but excited about finding out she has a grandson. She is kind to Toby, and invites him to stay and live with them. Toby likes the luxury and kindness, but hesitates. Toby, realizing he has some type of feelings for Bree, proposes to have sex with her (as having sex is the only way he knows to express love and emotion), saying that he will marry her if she wants to. Now Bree tells Toby that she was his father. Toby is angry that she had not told him that earlier, and disappointed in view of his fantasies how great his father might be. He leaves and travels on alone.

Back in Los Angeles, Bree has her surgery, but breaks down into tears in the recovery room. Toby, who bleached his hair and also went to LA, becomes an actor in gay pornography films. A glimpse of a film shoot reveals that he has trouble having an erection when required, in spite of using Viagra. Toby visits Bree, and the two reconcile. He shows a leaflet about an upcoming DVD in which he performs, and tells Bree that he can get her a discount. The film's final words of dialogue show that they have reached a level of mutual respect.

One of the major themes of the film is the personal journey toward self-discovery, according to interviews with the director and actors.

Trivia

The initial idea for the screenplay occurred in a conversation between screenwriter/director Duncan Tucker and intersex actress Katherine Connella. While discussing male/female perceptions, Connella shocked Tucker (they had been sharing a house for about four months at the time) with the revelation that she had been raised as a male.
This is the first non-Miramax film to be acquired by Harvey Weinstein and Bob Weinstein.
Dolly Parton wrote and performed the song played over the closing credits, "Travelin' Thru", which was nominated for an Academy Award. It was her second nomination, her first being "9 to 5", twenty-five years earlier.
A line spoken by the "peyote shaman" hitchhiker ("I'm a level four vegan; I don't eat anything that casts a shadow.") is a reference to a line "I'm a level five vegan" in Lisa the Tree Hugger episode of The Simpsons.
Toby claims that "The Lord of The Rings" is homosexual when he explains to Bree after she asks: "There's this big, black tower, right? And it points right at this huge burning vagina thing, and it's like the symbol of ultimate evil. And then Sam and Frodo have to go to this cave and deposit their magic ring into this hot, steaming lava pit. Only at the last minute, Frodo can't perform, so Gollum bites off his finger. Gay."