Dawson's Creek: Jack McPhee
After a brief fling with Joey (Katie Holmes), Jack (Kerr Smith) accepts his sexuality and comes out to his father and friends on Season 2 of Dawson's Creek. We'll never forget the scene with his father: "Ask me again! Ask me if I'm gay!"
And in case you mistakenly look back on DC as just another teen drama, get this: Jack's Season 3 kiss with his high school crush Ethan (Adam Kaufman) was the first male gay kiss ever aired on American network TV. That's groundbreaking stuff. (Unfortunately, Jack doesn't get the boy.)