Webcomics
Venus Envy
A webcomic by Erin Lindsey that details the adventures of a teenage transsexual girl as she adjusts to her new identity and deals with family and school.
Transe-Generation
A series of stories told in comic form about being transgendered. The sketches contain lots of MTF, FTM, and bigender inside jokes and political commentary.
Music & Performance
Athens Boys Choir -- Fagette
Athens Boys Choir is a spoken-word/queer/pop culture/hip-hop group consisting of a now solo member, Katz. Katz is a transsexual man whose performances deal with issues of gender, politics, love, sex, and everything in between.
http://www.athensboyschoir.com/
Julia Serano -- Cocky
Julia Serano is an Oakland, California-based writer, spoken word performer, trans activist, and biologist. She is a poetry slam champion and is also lyricist-guitarist-vocalist for the pop trio Bitesize. She is also the author of the book Whipping Girl: A Transsexual Woman on Sexism and the Scapegoating of Femininity.
http://www.juliaserano.com/index.html
Le Tigre -- Keep On Livin'
Le Tigre is a feminist electronic pop group consisting of members Kathleen Hanna, Johanna Fateman, and JD Samson. They attempt to integrate their political ideas in their music and make music that radical people can recognize their values in. This video is the official music video for their song, "Keep on Livin'", which deals with issues of coming out.
http://www.letigreworld.com
Other Gender-rockin' artists
Andrea Gibson (spoken word)
www.andreagibson.org
Dana Baitz (rock, soul)
http://danabaitz.com/
Katastrophe (rap)
www.katastropherap.com
Films
Documentaries
A Boy Named Sue
A Girl Like Me: The Gwen Arujo Story
The Aggressives
Call Me Malcolm
The Brandon Teena Story
The Cockettes
Princesa
Sir: Just a Normal Guy
Southern Comfort
Toilet Training
TransGeneration
Venus Boyz
You Don't Know Dick: Courageous Hearts of Transsexual Men
Other
Beautiful Boxer
Boys Don't Cry
The Crying Game
Hedwig and the Angry Inch
Ma Vie En Rose
Normal
Transamerica
Wild Side