Stanley (Felicity Huffman), soon to be Sabrina, is a 30-something pre-operative transsexual who has, a week before her surgery, issues that she will have to come to terms with. What she doesn’t count on is something that may not take care of itself as organically, the existence of a previously-unknown, delinquent teenaged son. At once, she is faced with juggling two roles that she has never played before: being a parent and being a woman. And so begins a story that is sketched on that most glorious and familiar of canvases: the open road. 

There are always indications that the bond that Sabrina is hoping to forge with her son Toby (Kevin Zegers) will be established eventually, albeit on its own sometimes-poignant, mostly-quirky terms. This dichotomy probably defines the tone of the movie itself: with a subject as delicate as this, I had expected a gingerly sort of approach that would use not-too-obvious sympathy to get a reaction. The script, though, understands that using humour to draw attention to human idiosyncrasies, and insecurities, works, and makes sure that the characters and the situations are peppered with it. Sabrina plays the unlikely heroine (hero?) perfectly, unsure of her actions, and quite expressively so, and yet always making sure that, outwardly, she is the embodiment of grace and dignity even as things around her start to unravel. In a telling opening scene, set to upbeat Latin vocals, as she’s dressing up and getting ready to leave her house, the conversation between her and the psychiatrist she is on her way to visit starts to be heard in the background. At first, it is mostly unintelligible due to the music. But as she walks to her bus stop, seemingly confidently, the "voices", a series of questions that her psychiatrist asks her about her sexual identity and her answers to them, grow increasingly louder as the music is slowly drowned out.  

Kevin Zegers is brilliant as the son, Toby, just bailed out of prison for prostitution, playing the self-involved post-adolescent that seventeen year olds, and especially troubled ones that find themselves in startlingly new situations, are capable of being. He reminded me so much of a younger Johnny Depp, and I found myself thinking that this is the kind of role that a 21 Jump Street Depp would’ve loved.  

It is this show, then, that is taken on the road. Quite literally. This classic backdrop with its infinite possibilities for inducing a sense of adventure and freedom never fails to work. Transamerica uses it not just as scenery but thrives on it and everything that comes along with it, adding to the sunset-tinged romance of it all. There’s the beat-up old car that’s done 230,000 miles but yet chugs along faithfully. There’re the panning shots set to perky country and bluegrass tunes, music that is quintessentially American. There are big bearded ZZ Top like Texans watching our adventurers at gas stations. There is the strange television-induced romance of the 24-hour diner, populated, invariably, by ogling truckers and men in cowboy hats with far-out twangs. It is in this ever-changing landscape that we see the relationship between Sabrina and Toby beginning to take shape. Sabrina’s valiant, hilarious attempts at establishing a bond are often met not with resistance but with a strange form of acceptance. Acceptance that makes her wonder if her son is even bothered with reading the situation at all. 

The avenues for comedic exploration (and that’s what this movie is, more than anything else - a comedy) are enhanced greatly by the introduction of extremely colourful fringe characters throughout the story. And these are people that are on the fringes of society: On their way, they stop by at a meeting of the Gender Pride Caribbean Cruise Planning Committee - a mish-mash of transgenders where there’s only one "GG" - short for Genuine (pronounced "Gin-u-wine") Girl. There is the hilarious episode of the hitchhiker (a hippie who calls himself a "Peyote Shaman") who drives away with their car while they’re all skinny dipping in a lake. And a lonely Native American guitar-strumming trucker who gives them a ride and is quite smitten by Sabrina at the end of it. It is at these times, when its boundaries are loose and its direction is meandering, that Transamerica is at its finest. 

What follows though, is a classic trap, and one that many movies fall prey to. In an attempt to provide resolution and tie up many of the wonderfully dangling loose ends that have been created, the movie takes a slightly forced turn. We meet the family, who, unlike the carefully brought-out quirks of nature we have met so far, hyperextend themselves into farce - an overtone that this movie is certainly above. But this is relatively minor, and again, Felicity Huffman’s presence manages to shine the light back to where it was, and where it should have always been.  

There are poignant moments, such as when Sabrina, for the first time in front of her family, dresses up (as a woman) for an evening out, and Toby is the only one not doing a double take when he sees her: "You look good."  

This is decidedly not a movie about transsexuals, but there is a subtle message asking for acceptance.