In 2005, he had a major role in the Academy Award-nominated independent film Transamerica, co-starring Felicity Huffman. Zegers' performance as Toby Osbourne, the street-hustling bisexual son of a trans woman (Huffman) was praised by several critics, and he won the Trophée Chopard for Male Revelation at the 2006 Cannes Film Festival. Director Duncan Tucker said he had to overcome his initial wariness over Zegers' good looks before casting him for the role. Varietys reviewer wrote that "Zegers... finds multiple dimensions in pic's potentially most clichéd character...," and The Hollywood Reporters critic said, "As a boy who considers sex his chief talent, Zegers... conveys Toby's essential sweetness and hunger for real affection, making him much more than just a vain or damaged kid."
