Straightboy Lessons
1999 · 8m · United States
Directed by Raymond Rea
Genres: documentary, essay film, LGBTQ+
Tones: contemplative, provocative
A celebratory, lesson-plan-structured look at a friendship between a transitioning female-to-male transsexual and a non-transsexual man, giving articulate advice on how to be a straight man.
Picked by Felix
The scouts
A 1999 essay-doc that flips the script on mentorship by having a trans man teach masculinity to a cis man—subversive enough that it probably felt genuinely transgressive at the time, and it still resists easy categorization as either celebration or critique, which is exactly the kind of premise that makes lesser scouts nervous.
Rea's structured use of the lesson-plan form creates a formal rigor that elevates what could be a simple conversation into something closer to a dialectical essay; the restraint in documentary language here—letting intimacy emerge through pedagogical distance—shows real craft awareness of the essay-film tradition.
The genius is in the casting choice or performance decision to let both voices carry equal weight and authority in the frame; there's a specific editorial or tonal choice here that refuses hierarchy, and that single commitment to parity—rather than making one subject the lesson-giver and the other the student—is what makes the whole thing work.