Transamerica stars Felicity Huffman as a preoperative male-to-female transsexual, Bree, who on the eve of her sexual reassignment surgery finds herself coming face to face with a son she never knew she had. Bree is working two jobs and living as a "genetic girl" in a poor Los Angeles neighborhood. She receives a phone call for Stanley (that is her pre-trans male name) from a jail in New York City where the heretofore unknown son has landed. Bree’s therapist Margaret (Elizabeth Pena) requires her to fully reconcile her past life as Stanley before she will sign off on Bree’s surgery. This set-up triggers Bree’s trip to New York and the picaresque road trip back to Los Angeles with the street hustler, her son Toby (Kevin Zegers).
There is one small catch — Bree withholds her real identity, or identities, from Toby. When she arrives in New York to have Toby released into her custody, she allows herself to be identified as a Christian missionary from the "Church of the Potential Father." This initial lie only leads to more lies. The fearful yet hopefully "passing" pre-op seems incapable of telling the truth at first (and conversations with her therapist indicate this is an ongoing problem for Bree). The potentially drug-addicted, street-hustling teen-aged fellow traveler picks up on this right away. Small on-the-road vignettes, by turns sardonic, slyly wise, sometimes lancing, sometimes fatuous, offer glimpses into the realities of living and surviving as a transgendered person in America today.
As Bree works through layer upon layer of coming out to Toby (and implicitly growing into herself), the plot unfolds along two parallel tracks, both typical of buddy movies. While she and Toby wrangle with each other, learning to trust in spite of betrayals and setbacks of that trust, they grow to know and love each other. And they experience numerous encounters of the screwball-wacky kind along the highway. Through it all, Bree discovers that she takes to motherly nurturing like a duck to water.
Many surprises await Bree and Toby on the road. Early on they make the mistake of picking up ayoung blondhippie hitchhiker (Grant Monohon), who (shades of Brad Pitt’s hitchhiker in Thelma and Louise) works his charisma on them both, to tragicomic effect. But then, Bree is outed in Kentucky during an early overnight stop along the road. They are to spend the night at the home of a "fellow missionary friend," who happens to be holding a support meeting for local transpeople, none of whom realize Bree has not come out to her young traveling companion. The camera’s point of view is with Bree, allowing the viewer to experience being "outed" with her.
Arriving at Bree’s childhood home in suburban Arizona (Bree’s current poverty in striking contrast to the suntanned opulence of her parents), the viewer is treated to the standard litany of dysfunctional family jokes, but with a transgendered twist. Fionnula Flanagan plays Stanley’s mother Elizabeth, Burt Young his father Murray, and Carrie Preston his rivalrous sister Sidney. As grandparents Elizabeth and Murray try to gain custody of their newly discovered grandson. Everyone is forced, finally, to start dealing with some not so jocular, long-standing, long unresolved realities. In the middle of the shenanigans comes a touch of grace for Bree, the unexpected mutual romantic interest with Calvin Manygoats (Graham Greene).
While it never exactly resolves the question whether Bree is father or mother or other to son Toby, they do know, and lovingly accept, they are family. Like the character Bree Osborne, Transamerica is not exactly drama, not exactly comedy, but definitely some of both. The delightful balancing of whimsy and deadly seriousness, light-hearted humor and cutting parody, a camp that is not exactly camp, all underscore the transgender message.