Writer/director Duncan Tucker's Transamerica (2005) is the sort of film that almost sends one running to the nearest "family-oriented" movie-review website just to see what sort of a thrombus a culturally conservative reviewer might have endured while watching this deeply sympathetic story of a pre-operative transsexual man and his teenage junkie/street-hustler son. And even for those who are bound to sympathize with the story's main characters, it isn't always easy to watch even if Felicity Huffman's Oscar-nominated performance is quietly fascinating. Huffman is Bree Osborne or at least she claims that's her name. For the moment, she's still Stanley Shupak, a fortyish transsexual who has struggled with gender-identity issues for her entire life and now, estranged from her family and isolated from virtually everyone but her therapist (Elizabeth Peña), is prepared to undergo gender-reassignment surgery, which is so comprehensive that even a gynecologist will not be able to determine her genetic background. It's an operation Bree has been looking forward to for some time up until now, she's been "living stealth" by virtue of hormone therapy and a somewhat-prim wardrobe. But when she receives a mysterious call from a young man who claims to be Stanley's son, she has no idea what to think. She even laughs it off in analysis, but her therapist surprises her by refusing to sign her surgery release until she rectifies the situation. As it turns out, Stanley/Bree does have a son, from a college assignation with a woman, and he's now in jail 3,000 miles from Los Angeles, in the downtown New York City lockup. Posing as a missionary, Bree bails out Toby Wilkins (Kevin Zegers) and even gives him $100, although he's little more than a confused, immature, strung-out hustler. Learning that he grew up in Kentucky, she then drives him to his childhood home. But after a confrontation with Toby's abusive stepfather, Bree has little choice but to bring Toby all the way to California, where he is convinced he will launch his movie career and find his real father.
The centerpiece of Transamerica is Felicity Huffman's performance as Bree, which earned both critical accolades and an Academy Award nod for Best Actress. And despite the fact that it's the sort of role that Oscar simply will never ignore, thanks to Huffman's ability to lose herself inside another person altogether, for the most part it's a success. It's easy to admire what's on the surface, to recognize that we're in the presence of "acting," but Huffman's real challenge was to find how much of Stanley exists inside of Bree, and then to communicate a fully rounded individual we are willing to follow throughout a movie. Not only is Bree an overly proper woman with her precise diction and flowery speech, but she's also committed, and if we want to suspect that there's something wrong with her, we eventually realize that sexual reassignment is the only thing in her life that she's entirely certain of. More complicated is Toby Kevin Zegers offers an equally poignant performance as an opportunistic bisexual teen, but it's much harder to sympathize with him, perhaps in part because his portrayal is too accurate. We want to pity Toby, but rarely are we inclined to like him. And with its Rain Man-esque road-trip, Transamerica wanders a bit too much in the middle-third, losing the thread of its own plot. However, the film recovers as Bree and Toby arrive in Phoenix to visit her estranged family, and if Fionnula Flanagan as Bree's mother is a bit too much a caricature of middle-class mores, at least the story's central conflicts finally find a sharp, well-controlled setting to play out in the final act. The Weinstein Company's DVD release of Transamerica features a solid anamorphic transfer (1.85:1) with Dolby Digital 5.1 audio. Writer/Director Duncan Tucker offers a commentary track, while other extras include interviews with Tucker & Huffman (18 min.) and Tucker & Zegers (10 min.), Dolly Parton's music video for "Travelin' Thru" as well as a "making-of" spot (4 min.), outtakes (3 min.), and the theatrical trailer. Keep-case.