A fine mess: Felicity Huffman and Kevin Zegers in Transamerica (Photo: The Weinstien Company)

Years before writing and directing his feature debut Transamerica, Duncan Tucker had considered starting his career with a different project altogether. It was an adaptation of a book he adored and which maintained the road movie tradition he wanted to follow for his debut. He knew it would take some massaging for an independent filmmaker to handle it, but still--it never really left his mind.

"Lord of the Rings," Tucker told me Tuesday, just hours before Transamerica's New York premiere. "It's a road story. I love those kinds of quest-adventure-fantasy books, and I was thinking, 'Gosh, how can I make an adventure? How can I make Lord of the Rings on a budget?' This is before the movies were made."

And in the end, sure--the films all share the story of a burdened hero's journey far from home. Moreover, they share a history of high-profile buzz: Felicity Huffman's performance as a pre-op transsexual coming to sudden terms with her family and her future netted her Best Actress honors last spring at the Tribeca Film Festival, as well as a similar nod for next year's Independent Spirit Awards and no shortage of attention in many film pundits' early Oscar pools. Tucker also received recognition at the Berlin and Deauville film festivals. The Weinstein Company made Transamerica one of its first post-Miramax acquisitions in August, partnering with IFC Films for a release this Friday.

Not a bad showing for a micro-budget gender- and genre-bender that Tucker describes as a "sheep in wolf's clothing." Huffman portrays Bree, a male-to-female transsexual who discovers a week before her operation that she is the "father" of a troubled teenage son. Despite Bree's protests, her therapist (Elizabeth Peña) insists that she travel to New York to reconcile her relationship with Toby (Kevin Zegers) before the surgery can occur. Bree poses as a Christian missionary to spring her son from jail, but her revulsion at Toby's drug-addled street hustling triggers her maternal (or paternal?) instincts to pluck him from his squalor and relocate him to his late mother's home in Kentucky. Toby has other plans--namely, gay porn stardom in Bree's hometown of Los Angeles--and their pairing soon hits the highway in a sort of bizarre hybrid of comedy, drama, buddy movie and, of course, road flick.

Transamerica's restless style-hopping is really its blessing and its curse in certain ways, with many of the script's prolonged efforts at humor batting well below the Mendoza line. Most of this shortfall has to do with a little too much irony. One particularly overcooked sequence features business-suited Bree on a camping stopover, clutching a roll of toilet paper and batting away potential snakes in the grass on her way to urinate. Tucker's narrative diversions into swimming holes, transgender dinner parties and, ultimately, the exurban red-state enclave of Bree's histrionic mother (Fionnula Flanagan) often appear contrived to fit the community conventions of the 100-minute road movie; they all wind up feeling forced or even truncated to some evolved climax.

However, for those keeping score at home (which is kind of my job, I suppose), Tucker's defiance of easy categorization results in a few well-crafted emotional wallops that do outlast his easier gags' rusty aftertaste. The guy can direct his ass off, introducing Bree and her condition with a discomfiting, matter-of-fact economy from the film's opening montage. Her vulnerability overrides her headstrength to no small degree, and Tucker's faith in Huffman allows for a patient and genuinely harrowing reversal of that imbalance along the way.

The internalization was so complete that Huffman, who wore a prosthetic penis named Andy (after the costume supervisor's ex-boyfriend, evidently) throughout production, says she was heartbroken when Tucker set Bree up to expose herself in the middle of her journey. The scene functions as The Un-Twist, in a way; Toby is outraged to discover what the audience has known since virtually the first frame, but that did not make it any easier for Huffman. "For some reason, when Duncan said actually, we're going to show Andy, I actually burst into tears," she told The Reeler. "I think it had been because I had been living with Bree so long that it felt like a travesty. It felt like a betrayal and I didn't want the crew to see it. Who cares? It's rubber! But I don't know. ... It puts you directly into Bree's experience, because the way you feel about her penis in that moment--like, 'Whoa! Oh, God!'--is exactly the way she feels about it. So it's kind of a wonderful piece of theater."

Transamerica's Huffman connection occurred well before she had even shot the pilot for the TV hit Desperate Housewives, for which she won an Emmy award earlier this year. Tucker sent her a script after seeing her perform off-Broadway. "When my producers got the $2.50 together to make the movie," Tucker told me, "they said, 'We can make the movie at this budget, but anybody you've ever heard of, you can't afford.' Luckily they were wrong and they were happy to be wrong. I got all my first choices."

Transamerica writer/director Duncan Tucker busts out his thinking cap (Photo: The Weinstien Company)

And as you would expect, Tucker naturally professes his love for all of them. But in the pair's exhaustive research and preparation for the film, Tucker and Huffman forge a specific authenticity that, however limited, gives something as inconsistent as Transamerica a chance to even out. In a year also boasting Cillian Murphy's memorable transgendered lilt in Breakfast on Pluto, Huffman achieves a different miracle by channeling a dark self-consciousness through Bree. It represents a fearless take on a socially conservative, essentially fearful woman threatened by her own biology--both internally and, in the form of Toby, externally. Huffman almost never acknowledges the dodgy irony Tucker imposes on her, choosing instead to leapfrog the narrative improbabilities that grow in proportion to Bree's own confidence. By the end of the film, Bree seems both encouraged and terrified by the reality of her womanhood. Huffman's resulting breakdown is among the most devastating since Cloris Leachman's own aged, irreversible torment at the end of The Last Picture Show.

Which brings to mind the bizarre problem of films like Monster's Ball, Monster and now Transamerica--original, well-made but nevertheless flawed films whose stunning lead performances illuminate the weaknesses surrounding them. I had to ask Tucker if this insecurity ever crept into his first film; after all, it is a hell of a problem to have. "I don't think so," he replied. "I think Felicity deserves every bit of attention she gets. She's amazing, and the movie is built around her character. It begins and it ends with her character. She's the one we follow. Everything's through her point of view, and that's how the movie was constructed. It gets inside the skin of somebody whom were not used to being inside the skin of. If I've done my job right, within 10 minutes, George Bush would watch this movie and start to feel for Felicity Huffman's character.

"But I'm really proud of all my other actors," Tucker added. "I think they hold their own, and I think that everybody--the scenes with Graham Green, the scenes with Fionnula, the scenes with Elizabeth Peña--these people are all present with Bree. I'm not worried about that." He even mentioned the potential for a TV or movie follow up to see how Bree, Toby and their road movie cohort fare. Which is a great idea, really--a Transamerica trilogy? I would be there in a second. I just hope Huffman does not have to wait through three films to finally get her Oscar.