The actor pictured with Maggie Gyllenhaal in the previous post on SherryBaby is Danny Trejo, the prolific character actor whose career happened by accident after beating drugs and a stint in prison. Trejo plays Dean, a fellow ex-addict, who becomes a friend, lover, and sounding board for Gyllenhaal's Sherry.
The performance is worth mentioning because Trejo has rarely gotten to play a sympathetic, 3d character as he does here. Trejo gives SherryBaby a much-needed note of warmth. Dean is the one character that Sherry connects with after prison and one of the few men who doesn't want something sexual from her.