Moennig's first major role was in the television series "Young Americans", playing Jake Pratt. She has played multiple lesbian roles: Shane McCutcheon in "The L Word"; Rosie's (Drew Barrymore) partner Jilly in "Everybody's Fine"; Candace, the lesbian lover of Sophia Myles' character, in "Art School Confidential"; and Lena, a press agent who works for Liev Schreiber's character, in "Ray Donovan". She has also pursued transgender roles, auditioning for the part of Brandon Teena in "Boys Don't Cry", and playing Cheryl Avery, a young transgender woman in the "" episode "".