When you see Transamerica, you may forget–even before the butter-flavoring has gone cold on your popcorn–that you're watching Felicity Huffman in the role of pre-operative MTF Bree Osbourne. It's a stunning physical transformation that might, on its own, bring curious Desperate Housewives fans into the theatre to see the new film. But the change to her exterior only hints at the layers of depth and insight that Huffman brings to the role in Duncan Tucker's charming new film.
We first meet Bree as she counts down the final days before her eagerly anticipated sex reassignment surgery. In Los Angeles, she is already living as a woman in the outside world (in “deep stealth” mode), working several jobs and living frugally in order to save money for the operation that will finalize her transition. But fate intervenes in the form of a phone call from an incarcerated son conceived when she lived as a man, a son she never even knew she had. She is quick to end the conversation and deny any connection to the boy, trying to convince herself that this unexpected development from her old life need not disrupt the new life she is so desperate to begin.
But Margaret, her therapist (played by Elizabeth Peña) won't let Bree off the hook that easily. Concerned that Bree's past—if left unexamined—may disrupt her ability to start an honest new life, she refuses to provide the required sign-off on the surgery unless Bree goes to New York to meet her troubled son.
Bree grudgingly goes to New York, poses as a concerned religious missionary and posts bond for her teenaged son Toby (Kevin Zegers). Toby was busted for prostituting himself, and Bree is horrified to see that he lives in such desperate and debauched conditions. Toby is suspicious of her motives at first, but soon realizes that this “church lady” could be his ticket out of hustling in New York. His big dream? To move to Los Angeles and become an adult film star.
Toby is a vulnerable but guarded young man, self-serving in a way that seems borne of his will to survive rather than any inherent selfishness. He idealizes the father he never knew (Bree when she was “ Stanley”), and was virtually orphaned by his mother's death. His initial toughness is a façade that conceals a lonely and sad youth without any support.
Bree hopes to avoid revealing her true identity to Toby, but guilt and a sense of obligation convince her to at least help get him out of his terrible situation. Her plane ticket back to Los Angeles is soon traded for a beat-up old station wagon, and the two head west, racing the clock as the date of her surgery grows closer.
The film is a “road movie” in the classic sense of the term, with the physical journey mirroring the internal journey experienced by both Bree and Toby. As you would expect, their relationship to one another changes as well. Initially more controlling and disapproving of his behavior, control-freak Bree loosens the reigns on the sloppy and reckless Toby. And as they encounter obstacles to their return to Los Angeles (too many to mention) they grow more trusting and reliant on one another.
But for most of the trip, Bree keeps both her transgender and parental identities hidden from Toby. It's a strategy that backfires when he discovers the truth. To his credit, Toby is disturbed by Bree's dishonesty, not her transgender identity, and his faith in her is shaken. There is a lovely scene in which necessity requires that the two travelers stay with some of Bree's transgender friends in Texas. It is Toby who defends them as “nice” when Bree nervously apologizes to him for their collective appearance.
While Bree's initial impulse is to “save” Toby from his life as an indigent hustler, it is Toby who, in a way, rescues Bree when they land on the doorstep of her estranged parents in Arizona (played by Burt Young and Fionnula Flanagan—in a brilliant diva performance that could drive YOU to family therapy). He recognizes and empathizes with the way in which Bree is unseen and misunderstood by her own family.