Whenever independent movies have nothing much on their mind, they usually hit the road, where the purposefulness of narrative can give way to something less defined, an aimless drift sprinkled with quirky encounters and occasional revelations. On these back roads, characters find themselves, though Felicity Huffman, the pre-op male-to-female transsexual at the center of Transamerica, already knows herself pretty well. A prim, composed woman in the mold of a '50s housewife, complete with drag-queen makeup and a wardrobe clogged with colorful dress suits, Huffman has her identity almost entirely worked out. There are only two nagging problems: She still has a penis, and she's just learned that she's a father. She's scheduled for the last and most decisive of a series of surgeries, but the fatherhood issue takes some painfully earnest soul-searching, stretched out along the quaint country roads leading from one coast to another. It turns out to be an awfully long trip.
A week before the operation, Huffman gets a phone call from a young delinquent looking for his father. Though she tries to retreat from her responsibilities, her psychiatrist (Elizabeth Peña) refuses to sign a consent form for the surgery until Huffman confronts the situation. Flying from Los Angeles to New York, Huffman pretends to be a Christian missionary when she bails her teenage son (Kevin Zegers) out of jail on shoplifting charges. After witnessing Zegers' squalid living conditions, paid for by his dangerous life as a street hustler, Huffman offers the troubled kid a ride to the West Coast, where he can pursue his dream career as an adult-film star. The road leads them through a botched reconciliation with Zegers' stepfather, campouts under the stars, and encounters with a peyote-toking hitchhiker and an Indian cowboy (Graham Greene) with a half-blind eye for Huffman.
Best known for her reliably sharp turns on TV shows like Sports Night and Desperate Housewives, Huffman intermittently rescues Transamerica from bathos with her brusque wit, swatting away the victimization elements that figure into most films about transsexuals. As a woman playing a man becoming a woman, Huffman leaves the overacting to the makeup job, which suggests mannishness by way of Bela Lugosi. Her dignity and composure are real, but everything else in the film rings false, from Zegers' baby-faced midnight cowboy to the kitschy grotesquerie of roadside wigwams and Huffman's childhood home in Arizona. Without Huffman, it's hard to imagine Transmerica gaining much traction outside the most obscure Sundance satellite festivals. But with her… an Oscar?