She's a Boy I Knew (2007)

Using interviews, animation, old family footage, and voice mail, Vancouver filmmaker Gwen Haworth documents her male-to-female gender transition partially through the voices of her anxious but loving family, best friend, and wife. Calling for a new era of DIY transgender self-representation, Haworths feature debut is a comic, heartbreaking, and uplifting autobiography that breaks away from the marginalized depictions of transsexuals that populate mainstream media and focuses on the interpersonal relationships of a family who unexpectedly find their bonds strengthening as they overcome their preconceptions of gender and sexuality.

http://www.imdb.com/title/tt1095496/