I never saw Waterloo Road or She’s The Man.
The first documentary I saw was You Don't Know Dick: Courageous Hearts of Transsexual Men (1997).
I remember seeing the film Boys Don't Cry (1999), a dramatization of the real-life rape and murder of Brandon Teena. The film came out a year after I transitioned. I remember watching it at home, probably on VHS, maybe a few years after it came out. That may have been the first in-depth narrative portrayal of a trans guy I saw on screen.
After that, it never occurred to me that there could be any other portrayal: a trans guy who survives long enough to transition or just to be recognized in his gender, is more or less accepted and socially integrated, is more or less happy, and (just maybe, as a bonus) is into guys.
Didn't see it until a few years ago, when I was about 40, in the character of Theo Putnam in the Chilling Adventures of Sabrina. Wasn't expecting it. Pleasant surprise.