Transamerica is a 2005 independent comedy-drama film produced by IFC Films and The Weinstein Company. The film tells the story of Bree, a transgender woman (Felicity Huffman), who goes on a road trip with her long-lost son Toby (Kevin Zegers).

The film is marked by an Academy Award–nominated and Golden Globe–winning performance by Huffman, who is also known for her performance in Desperate Housewives.

One of the major themes of the film is the personal journey toward self-discovery, according to interviews with the director and actors. The screenplay was inspired in part by conversations between screenwriter/director Duncan Tucker and his then roommate Katherine Connella.

Plot

One week before her vaginoplasty, a conservative Transgender woman named Sabrina 'Bree' Osbourne (Felicity Huffman) receives an unexpected phone call from a young man named Toby Wilkins (Kevin Zegers), a 17-year-old jailed in New York City. He asks for Stanley Schupak (Bree's birth name), claiming to be Stanley's son.