It would turn out to be a classic teen TV drama moment: Dawson Leery, the eternal idealist of late '90s adolescent sudser "Dawson's Creek," watches as his soul mate embarks on a love affair with his best friend. As she walks away, Dawson's "ugly cry" absorbs his face.
"God, do I remember that moment," recalled James Van Der Beek, the crier in question. "It wasn't scripted for me to cry, it just happened." He had all but forgotten that scene at the end of the show's third season until a few years ago, when it resurfaced on YouTube and Twitter. "All of a sudden, six years of work was boiled down to one seven-second clip on loop," he said. "It became a joke."
A joke that, though he may be the punch line, Van Der Beek is now trying to reframe. When ABC's new comedy "Don't Trust the B- in Apartment 23" premieres Wednesday, Van Der Beek will be joining a growing list of actors - Matt LeBlanc, Larry David, Ricky Gervais - playing meta-versions of themselves. It's the 35-year-old actor's first major comedy series, and it finds him playing a supporting role as the "Oh my God, that's really him" best friend to the mischievous roommate from hell mentioned in the show's title and played by Krysten Ritter.
The heightened version of "The Beek From the Creek," as he is nicknamed in the sitcom, is a smarmy has-been who is trying to hold on to his former glory - whether by seducing fans to the wrenching notes of the "Dawson's Creek" theme song "I Don't Want to Wait," earnestly competing in "Dancing With the Stars" or being the spokesman for his character's fictional brand, the exceptionally snug Beek Jeans. (Its slogan: "Put your cheeks in a Beek.")
Series creator Nahnatchka Khan originally had in mind Lance Bass of boy band 'N Sync to play a version of himself. "When I was writing the script in my pajamas, I was like 'Oh, this would be funny,'" she said. "But when it actually was becoming a real thing, we needed someone to hold their own against Krysten."
Van Der Beek's participation would have been unthinkable when he was in the eye of the teen mania storm: "I took myself way too seriously," he said. But that changed when the tempest subsided and showed no sign of returning.
"The ego certainly is the biggest obstacle as an artist or performer, so any chance you get to destroy that is really healthy," he said.
Seated on the balcony of West Hollywood's Soho House, Van Der Beek still speaks with the mellifluous voice that propelled all that long-winded Dawson dialogue. And his girlish giggle pops up periodically. But his career outlook has matured - because it had to. "You start to realize you're protecting some image of yourself that you think other people have. ... And you think, 'What am I protecting?' It doesn't make any sense."
The struggle was all the thornier given the way his "Dawson's Creek" costars had managed to thrive. Joshua Jackson got a central role in Fox's cult drama "Fringe." Katie Holmes appeared in films before taking on her highest-profile role as Tom Cruise's wife. Michelle Williams became an Oscar-nominated movie star.
"I think I've probably been the slowest starter out of the gate," Van Der Beek said. Exhausted and jaded after the series ended, he recalled a telling moment, while working on an independent film, in which he caught himself wondering how many setups were to be done before he could go home.
"Being at work felt like torture. And it shouldn't feel that way. I just wasn't ready. But once it went from 'Oh my God, I love you' to 'Oh my God, I used to have such a crush on you when I was little' - when that turn happened, that's when I realized I needed to get back to work. Fast."
But Hollywood doesn't wait, and for the Connecticut native that was a strange reality.
"Here I was, a much better actor than I was when I was 20, but Hollywood had already moved on to whoever was the hot, fun, new thing." He said this kicked off a period of reflection. He began practicing kabbalah and, after a failed marriage, remarried and now has two young children.
Professionally, he sought comfort in writing and played bit parts in TV movies and TV series ("How I Met Your Mother," "Ugly Betty") until landing a role on NBC's short-lived medical drama "Mercy" in 2010.
"I always got my fair share of drama offers," Van Der Beek said. "I just wanted to try something different. I had a real awakening on my part to just stop being so precious with my career."
Cue the self-mockery. "As the years wore on and I passed on more stuff, less stuff started getting offered. And I had this realization where I just thought, 'If something sounds fun and I haven't done it before and I get a kick out of it, I'm just going to say yes.'"
That philosophy led him to approach Funny or Die - he asked for a meeting that would lead to a series of self-spoofing spots on the comedy website. He also played himself - killing unicorns with lasers, no less - in Kesha's music video for "Blow."
The comedy offers followed, "Don't Trust the B-" among them.
"We saw the Funny or Die stuff," Khan said. "I knew that he was willing to lampoon himself a little bit and that he could bring it. And he has this easygoing charm. We got really lucky."
Van Der Beek just hopes he can deliver as himself.
"Wouldn't it suck if, after all this, they decide Lance Bass could do a better job as me?"