Transamerica
One week before her vaginoplasty, a conservative transgender woman named Sabrina 'Bree' Osbourne (Felicity Huffman) receives an unexpected phone call from a young man named Toby Wilkins (Kevin Zegers), a 17-year-old jailed in New York City. He asks for Stanley Schupak (Bree's birth name), claiming to be Stanley's son.
Bree was previously unaware she had a son; she now wants to break with her past and renounce him. However, Bree's therapist (Elizabeth Peña) refuses permission for her operation if she does not face up to her past ties before facing her new future.
Bree flies from Los Angeles to New York City to bail Toby out of jail. Toby is a foul-mouthed runaway plus small-time drug user and male "hustler". His mother committed suicide when he was a child after which he was raised by his stepfather, whom he says he does not want to see.
Bree pretends to be a Christian missionary 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 the town of Callicoon, Kentucky, it turns out that Toby's stepfather was very abusive and he molested him several times in his youth. To Bree's dismay, her plan to leave Toby with him fails miserably. Bree and Toby continue driving to Los Angeles together. They also stop by a house in Dallas where a group of transgender women (many of whom are old friends of Bree's) are hosting a gender pride gathering. Later on in the trip, when Bree has to urinate, Toby accidentally discovers that Bree has male genitalia. He tries to be open-minded about it, but is angry that Bree had not told him prior to his unintentional discovery.
After their car and money are stolen by a young hitchhiking hippie who calls himself a "peyote shaman" (Grant Monohon), Toby makes some money by prostituting himself to a truck driver. 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. Calvin and Bree hit it off very well and flirt a little, which disturbes Toby. Here they find her pampered and self-centred mother Elizabeth (Fionnula Flanagan), her Jewish father Murray (Burt Young) who seems to be dominated by Elizabeth, and her rebellious and sarcastic sister Sydney (Carrie Preston). Elizabeth disapproves of Bree's transsexuality (it is mentioned that she has been estranged for some time from her because of her transphobia), but is astonished to find 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 because he does not like how disrespectful they are to Bree. Realizing he has feelings for Bree, he tries to seduce her, saying that he will marry her if she wants. Bree realizes she must tell Toby the truth immediately, saying that she was his real father. Toby is appalled and infuriated that Bree had not disclosed this earlier. Overnight he steals money and valuable antiques from the house and disappears. Heartbroken, Bree returns to Los Angeles via a plane ticket bought by her parents. Her family finally accepts her calling herself Bree, she has a completely successful surgery, but she is unhappy because she feels she will never again see or hear from Toby. The therapist visits Bree in recovery and Bree, after she confesses she made a mistake, sobs and cries heavily on her shoulder.
Some months later, Bree is surprised to see Toby knock at her front door. Bree invites Toby inside and he reveals to her he has turned 18, bleached his hair blonde, and has become an adult actor in gay pornographic films in Los Angeles. Bree is vibrant, happy, and enjoying her job as a waitress at the restaurant where she was formerly washing-up. Bree and Toby reconcile, seemingly happy to have each other.
psychedelic, queer