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To Wong Foo, Thanks for Everything! Julie Newmar
1995 · Film · 108 min
Directed by Beeban Kidron
Veteran drag queens Vida Boheme and Noxeema Jackson take novice Chi-Chi Rodriguez under their wing on a madcap road trip across the country to compete in the Drag Queen of America pageant in Los Angeles.
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A bunch of movies off hand that weren't mentioned elsewhere. This doesn't include tv shows, the two I remember off hand are M*A*S*H and The Kids in the Hall.
1999: Hilary Swank won best actress for Boys Don't Cry.
1982: Julie Andrews nominated for Victor/Victoria
1983: Barbara Streisand in Yentl -- before she became the effect.
1996: Robin Williams and Gene Hackman in The Birdcage.
1995: Patrick Swayze in To Wong Foo, Thanks for Everything! Julie Newmar
1994: Mignight in the Garden of Good and Evil directed by Clint Eastwood
1992: The Crying Game
According to Wikipedia [1], comedy TV shows with LGBT characters by decade (which is probably a good proxy). Ellen's "coming out" episode was in 1997.
70s: 12 80s: 11 90s: 28 00s: 45
Willing to wager the trend is similar to movies.
We had (just the ones I can recall off-hand, but had to lookup years):
Paris is Burning ('90) My Own Private Idaho ('91) Fried Green Tomatoes ('91) Philadelphia ('93) To Wong Foo, Thanks for Everything! Julie Newmar ('95) Jeffrey ('95) Birdcage ('96) Bound ('96) In & Out ('97) Boys Don't Cry ('99)
Of course, most of these role were filled by cis people.
[1] https://en.wikipedia.org/wiki/List_of_comedy_television_series_with_LGBT_characters