“Sideways” turns inside out in “Transamerica.” Laugh-out-loud funny, tartly off-color and ultimately touching, this road movie involving the cross-country adventures of a persnickety transsexual, and the runaway street hustler son whose existence is news to her, reps a triumphantly genre-bending big-screen bow for writer-director Duncan Tucker. An adventurous U.S. distrib willing to put marketing muscle behind an outspoken comedy, one that feels like vintage John Waters scripted by Alexander Payne and Jim Taylor, could reap controversy of the former’s works and approach kudos-driven B.O. of the latters.’ Internationally, it should travel well beyond niche fests to develop crossover appeal in theatrical and homevid.
On the verge of qualifying for the surgery that will complete her transformation from Stanley to Sabrina Claire Osborne, primly wry Bree (Felicity Huffman) is given one last hurdle by therapist Margaret (Elizabeth Pena): She must spring Toby (Kevin Zegers), a previously unknown son from a long-ago hetero encounter, from detention on charges ranging from street-hustling to “shoplifting a frog.”
Sullen Toby believes Bree to be a Christian missionary, and has no clue that she’s a he, or that he’s her/his son. On these terms, they head from New York to Los Angeles by car, Bree to have her operation and Toby to pursue stardom in the porn industry.
Thinking she’ll ditch the boy with a stepfather in Kentucky, Bree is shocked to learn that Toby’s reason for escaping involved parental abuse. In Dallas, the pair stumble upon a cozy suburban coffee klatsch of the “gender gifted” in various stages of transformation. When their car is stolen in New Mexico by an open-minded but larcenous hitchhiker, they thumb a ride with affable Calvin Two Goats (Graham Greene). On the way to Phoenix, the courtly cowboy becomes quietly smitten with the increasingly disheveled Bree.
Pic kicks into high gear at about the hour mark, as Bree reluctantly knocks on the door of her disapproving upscale parents Elizabeth and Murray (Fionnula Flanagan, Burt Young), and rehabbing younger sister Sydney (Carrie Preston). “We all look much happier than we are,” Sydney announces to shocked restaurant patrons as the supremely dysfunctional family ventures out to dine. By the end, however, they’ve made peace with each other as both relatives and individuals.
The principal keys to Tucker’s success are casting and tone. Thesps by and large play it straight, allowing humanity to survive the shock value of an episodic script inspired by helmer’s experience with transsexuals and runaways. This is typified by the most eye-opening sequence, in which Toby glimpses Bree relieving herself by the side of the road and realizes what’s going on.
As with “The Crying Game” and “Boogie Nights,” any resulting controversy will be for all the wrong reasons. In a bizarre resume twist, this is the second film, after P.T. Anderson’s “Boogie,” to involve both a prosthetic male member and William H. Macy, who serves as exec producer here and is married to Huffman.
In a far cry from her current gig on tube hit “Desperate Housewives,” Huffman is spectacular as the complex Bree, at once proud and terrified of how she is, who she wants to be, and what she must endure to get there. Zegers, from recent “Dawn of the Dead” remake, finds multiple dimensions in pic’s potentially most clichéd character, while Flanagan steals her scenes as a flustered red-stater whose maternal instinct finally trumps her blind prejudice.
Discreetly strong tech contributions are led by Mark White’s spot-on production design, which conveys the cluttered conservative charm of mid-America on a series of locations in New York State and Arizona. David Mansfield’s fine score is supplemented by a clutch of diverse tunes ranging from Chopin to The Nitty Gritty Dirt Band.