Think of male-to-female transsexuals onscreen and the first thing that probably pops to mind is Kathleen Turner as Chandler's dad on Friends. There isn't exactly a rich tradition of serious, affecting stories about such people, so Transamerica gets points for being exactly that. Plot-wise, it's much more conventional than you might expect, but Tucker's strength is in creating real and empathetic characters nothing like the caricatures in other movies.
Tucker takes a risk by casting Huffman as Bree, a man in the process of transitioning into womanhood. Before undergoing surgery, though, Bree learns that she has a son from her one heterosexual encounter, and her therapist (Peña) insists that Bree reconcile with her offspring before she can move on with her transition.
She flies from California to New York City, taking her far outside of her comfort zone as she confronts teenage Toby (Zegers). Toby is a nightmare to the prim Bree: He's a drug-user and a petty criminal and a bisexual whose ambition is to star in gay porn. Posing as a Christian missionary, Bree doesn't reveal her true identity, but offers to take Toby on a road trip to California.
Transamerica mines clichés from both road movies and mismatched-buddy films, and you know that by the end, the squabbling Bree and Toby will develop not only an understanding but also a familial love. Bree, in turn, will become a more complete person as she heads into her surgery. Predictability aside, none of the familiar elements feel forced, and Huffman and Zegers give real, heartfelt performances.
Huffman's won numerous awards for her portrayal of Bree, and she pulls off an incredibly difficult feat, carrying herself as a man trying to appear as a woman. At first her mannerisms seem false, but once you realize that that's exactly how someone like Bree would come across, it becomes much easier to take. The film succeeds on the goodwill of the performances and the message, which make up for the relatively simplistic story.