1 of 25
1992 — BILLY DOUGLAS (Ryan Phillippe), One Life to Live (ABC)
Network TV's first gay high schooler (played by a teenage Ryan Phillippe), came out to dispel rumors that he was being molested by the town's compassionate pastor — and then, shortly afterward, bolted to attend Yale. ''I would worry, 'What will the people at school think?','' Phillippe admitted 18 years later to Men's Health, ''And they fully shunned me in a lot of ways...but it ended up being an incredible experience and such a time of growth.''
2 of 25
1994 — RICKIE VASQUEZ (Wilson Cruz), My So-Called Life (ABC)
''I still receive emails and messages from people discovering the show,'' says Cruz, who played primetime's first gay teenager on My So-Called Life 17 years ago, ''I have letters that I've kept. Tear-stained letters. It's as if there was this void and, finally, I was able and willing to step into it. I was happy to do it. We never received a negative word [about Rickie]. Rickie was the heart and soul of that show. He was the most spiritual person and he was the person who had the best view on sex. Period.''
3 of 25
1999 — JACK McPHEE (Kerr Smith), Dawson's Creek (The WB)
Initially introduced in season 2 as a love interest for Katie Holmes' Joey Potter, Jack opened up about his sexuality that winter — and a year later engaged in TV's first onscreen romantic male kiss. According to creator Kevin Williamson, Smith had only minimal reservations when he first heard his character was coming out, ''I asked, 'Is this a problem for you?' He said, 'Not if I get a juicy part. My biggest fear is that I'll have this coming out story and then I'll just sort of gradually become the gay character in the background.' I said 'Not with me, you won't.'''
4 of 25
2000 — WILLOW ROSENBERG (Alyson Hannigan) and TARA MacLAY (Amber Benson), Buffy the Vampire Slayer (The WB)
Benson's two-episode arc as Willow's Wicca-loving college friend Tara expanded into a multiseason stint as the girls grew into the series' most functional couple. ''My hope is that people won't be so anxious to put a label on it like she's become a lesbian, or it's just a phase, or she's bisexual,'' Buffy creator Joss Whedon told EW in 2000, ''I didn't want to make it a big issue. As soon as you start to hammer out a definition, it becomes kinda icky. It stops being just about these two people.''
5 of 25
2002 — JESSIE SAMMLER (Evan Rachel Wood), Once and Again (ABC)
After 15-year-old Jessie returned best friend Katie's (Mischa Barton) advances, the pair sealed the deal with not just one lip-lock, but two — marking the first time on primetime that a lesbian couple kissed more than once during a single episode. ''There was one affiliate that didn't air it,'' remembers co-executive producer Winnie Holzman (who also created My So-Called Life), ''but I had a lot of incredible network support. I think people censored themselves and assumed they couldn't do certain things. I did want a gay character and I was thinking about my own teen years when I wrote that.''
6 of 25
2003 — MARCO DEL ROSSI (Adamo Ruggiero), Degrassi (The N)
School valedictorian Marco was the first of eight (and counting) gay major characters on the groundbreaking Canadian teen soap, which was tackling gay plotlines as far back as the 80s and now features a female-to-male transgender teen. Says co-creator Linda Schuyler, ''There are some fundamental teen issues — issues of teen pregnancy, issues of sexuality. I never would have thought about doing a transgender character in the original Degrassi Junior High [the show's earlier incarnation]. When we started there were no gay, lesbian, bisexual clubs in school, now you see them in small towns.''
7 of 25
2005 — ANDREW VAN DE KAMP (Shawn Pyfrom), Desperate Housewives (ABC)
The scheming — and openly homosexual — Andrew defied network stereotyping with his bad-boy antics (running over the neighbor's mother, seducing his own mom's boyfriend) to be the quintessential Desperate Housewives character. ''He's narcissistic, vain, and then gay. I like how it doesn't define him,'' Pyfrom told EW in 2007.
8 of 25
2005 — ASHLEY DAVIES (Mandy Musgrave) and SPENCER CARLIN (Gabrielle Christian), South of Nowhere (The N)
The on-again/off-again couple (''Spashley'' to fans) were a TV milestone: the first gay teen partners to be played by two top-billed series regulars.
9 of 25
2005 — MARISSA COOPER (Mischa Barton), The O.C. (Fox)
Broody Marissa found six episodes of turbulent love with club manager Alex (Olivia Wilde), until her lingering feelings for an ex sent Alex packing — a departure that was, in part, the result of network pressure. ''We were excited about the possibility of keeping her in the mix and keeping the Marissa-Alex story alive,'' remembers executive producer Stephanie Savage, ''Then the combination of Olivia's schedule and network feedback made the case that we had to wrap that up sooner.''
10 of 25
2007 — KENNY (Rami Malek), The War at Home (Fox)
The first openly gay teen on a network family sitcom, neighbor Kenny came out during the Long Island-set comedy's second season, after which his Muslim parents shunned him and the Gold family took him in. Hilarity ensued, seriously, as Fox wrung laughs from his first date, his first boyfriend, and his first dance — and even, sadly, his parents' abandonment.
11 of 25
2007 — CALVIN OWENS (Paul James), Greek (ABC Family)
Out from the series' start — and to his parents before that — frat boy Calvin stood down his frat brother's prejudices to ascend to the presidency of Omega Chi. ''I definitely wanted to be ahead of the curve with Calvin,'' says Greek creator Patrick Sean Smith, ''I wanted to see a gay character who wasn't victimized by his sexual orientation, somebody I wish I had when I was coming out to see that it's a normal process.''
12 of 25
2008 — ERIC VAN DER WOODSEN (Connor Paolo), Gossip Girl (The CW)
After being outed at the dinner table, sweet mousy Eric admitted to getting physical with BFF Jenny's boyfriend in true Gossip Girl style. ''The only sensitivity The CW had to Eric's storyline was his age,'' claims executive producer Stephanie Savage (who also worked on The O.C.), ''They felt like a coming-out story was a late high school or college story and Eric was 14. But our impression was kids these days are coming out much sooner.''
13 of 25
2009 — MARSHALL GREGSON (Keir Gilchrist), United States of Tara (Showtime)
Fourteen-year-old film lover Marshall is wholly accepted by his mother (Toni Collette), but not by one of her more gruff multiple personalities.
14 of 25
2009 — KURT HUMMEL (Chris Colfer), Glee (Fox)
Within a year of the show's launch, the season 1 supporting character managed to break out of the ensemble and take center stage with anti-bullying story lines, a new crush, more solos, and a Golden Globe win for the actor. ''It's the first positive portrayal of a gay character, especially of a kid, without him being a punching bag, or a punch line, or an annoying sidekick,'' says Colfer, ''I realized after we filmed the first 13 episodes that the story line is much bigger than me. It's such a powerful, powerful statement.''
15 of 25
2009 — GRIFFIN (Brando Eaton), The Secret Life of the American Teenager (ABC Family)
The teen-sex heavy show's first gay youngster, Griffin is also one of the kids who agreed to a high school chastity pact.
16 of 25
2009 — GRETCHEN BERG (Madeline Zima), Heroes (NBC)
The college frosh started out as as a Claire's (Hayden Panettiere) ally-in-evil-fighting and then evolved into a (highly publicized) love interest for the ex-cheerleader.
17 of 25
2010 — JUSTIN SUAREZ (Mark Indelicato), Ugly Betty (ABC)
Justin's coming out episode was four years in the making, and was topped with a very cute same-sex teen kiss during the show's final season, ''When I signed on to do Ugly Betty, I was 11 years old,'' says Indelicato, ''I don't think they knew at the time what they wanted to do [with Justin]. It started off that he was going to be the funny, flamboyant, kind of questionable kid... I think we were all scared when the time really came. When we did the historic kissing scene, I was very nervous. I didn't know how it would be received.''
18 of 25
2010 — ADRIANNA TATE-DUNCAN (Jessica Lowndes), 90210 (The CW)
Adrianna got over ex-boyfriend Navid by joining a band and exploring her feelings with new best friend Gia (guest star Rumer Willis). ''It didn't feel like she was a lesbian who was covering by being straight. It felt like she could experiment and that there was more sort of fluidity for a teenage girl there,'' says showrunner Rebecca Sinclair, ''I feel like we should have bisexual characters who are genuinely bisexual — we should have people doing all sorts of exploring, every aspect.''
19 of 25
2010 — ALISTAIR (Harvey Guillen), Huge (ABC Family)
My So-Called Life creator Winnie Holzman revisited the complicated lives of teens with Alistair, a fat-camp outcast who was unpopular, overweight, and struggling with his sexuality. Says Huge executive producer (and Holzman's daughter) Savannah Dooley, ''I don't think of Alistair as a gay character, but as someone who's exploring gender identity. We left his character in a pre-transitional state. I thought of him as someone to whom gender is not a concern.''
20 of 25
2010 — EMILY FIELDS (Shay Mitchell), Pretty Little Liars (ABC Family)
A teen soap about hot young, gossipy girls doesn't have to just be about straight ones, as proven by Emily, whose experimentation turned into a real coming-out story. Says Mitchell, ''I think it's so cool how the writers have shown how supportive her friends were and how supportive her father was. [And he's a] military man, who you thought would most likely not take it so well. I think it gives people courage.''
21 of 25
2010 — JESSE (Dane DeHaan), In Treatment (HBO)
The show's third season introduced a 16-year-old therapy patient who was comfortable with his sexuality but not with meeting his birth mother.
22 of 25
2010 — BLAINE (Darren Criss), Glee (Fox)
Kurt's journey to becoming a confident young gay man is being helped along by self-assured crush Blaine. ''Blaine was never going to be Kurt's love interest at all. He was gonna be much more of a mentor character, but they had so much chemistry and there was such an immediate outcry,'' claims co-creator Ryan Murphy. ''We all want to see Kurt happy,'' adds Criss, ''and like all great love stories, if you have two people that can be together you've got to hold it up.''
23 of 25
2010 — TEDDY MONTGOMERY (Trevor Donovan), 90210 (The CW)
Producers originally wrote spoiled tennis-pro Teddy as a dime-a-dozen hunky ladies man, but a year into his story realized that he must be overcompensating for something — like a crush on his former roommate. ''Things start to make sense as you learn his backstory,'' Donovan says of the switch, ''You start to look at the way he lives his life and how he bounces around, never really having a solid girlfriend. It breaks down the stereotype. This is a little more shocking and realistic.''
24 of 25
2010 — TEA MARVELLI (Sofia Black-D'Elia), Skins (MTV)
Sexually active and out to her friends, Tea (a character created for the U.S. version of the British show) has yet to tell her Jewish-Italian family that she's a lesbian and struggles with her feelings after fooling around with a male friend. ''There was some discussion that I had changed a gay male character to a gay female character, that I'd taken the easy option,'' says co-creator Bryan Elsley, who also fears how the gay community will reacted Tea's straight dalliance. ''We're just trying to express how screwy people's lives can be, we're hoping that people in the gay community will recognize something in those stories.''
25 of 25
2010 — IAN GALLAGHER (Cameron Monaghan), Shameless (Showtime)
Already called the ''anti-Kurt Hummel'' by Vanity Fair, tough, streetwise Ian (who is based on a character in the show's original British version) is in the Army ROTC and having an affair with his married male boss at a local grocery store.