As for the Topic of the Day... I'm not really sure which ones were my "firsts", but these are the ones that stick with me...
TV: "Doing Time On Maple Drive"
"Punky Brewster"

"The Fifth of July" - via PBS's "American Playhouse", thus TV. I know it's not a gay-themed play, but seeing this a few years before I came out, well...
"An Early Frost"
"Tales of the City"
Books: "The Lord Won't Mind" - and the rest of that trilogy by Gordon Merrick.
"The Front Runner"
"Family Dancing", "The Lost Language of Cranes" - I still prefer David Leavitt's earlier writings.
"The Best Little Boy in the World"
"On Being Gay"
-And stacks of other books that I bought and browsed at Lambda Rising in DC.
Plays: "Quisbies" - The Kennedy Center had a "San Franciso Festival" many years ago. Theatre Rhinoceros was invited to be a part of the festival, and they presented "Quisbies". -It also coincided with one of the last displays of the full AIDS Quilt on the Mall in DC.
"Torch Song Trilogy"
"Take Me Out"
Movies: "Making Love" - I never saw the movie until years after it's initial release, but, boy, did the commercials and "buzz" for the movie pique my interest.
"Maurice"
"My Beautiful Laundrette"
"Longtime Companion" - I remember watching this with some friends when it originally came out. Sadly, most of those friends were basically watching their lives on screen. I still watch this movie every now and then, and I still miss those friends.
*Coincidentally, my "anniversary" is coming up in a few days... 23 years... WOW!