Photography by JUCO | Retouching by Anna Glen at Wet Noodle

The Moment: September 23, 1984: The first Folsom Street Fair

Hip deep in shooting the second season of HBO's Looking, Jonathan Groff leads four of his cast mates into the Phoenix, a legendary rock 'n' roll hideout in San Francisco's Tenderloin district, for a quick costume change. He makes a beeline for a pair of ass-less chaps, and the others clamber into their own mix of vintage Levi's and leather gear. But Groff can't decide between two accessories from Mr. S, the local kink outfitter. "Can I get the long whip again?" he asks, then changes his mind. "Wait, I like this one better."

He explains later, "Photo shoots can be so awkward, so I just play pretend like I'm a little kid. Growing up, we had a bin of costumes -- an old man or Peter Pan or a princess or whatever -- and to get outside the weirdness I just think, This is like dress-up time."

Groff and his rowdy band of brothers -- from left, Raul Castillo, Murray Bartlett, Frankie J. Alvarez, and Russell Tovey -- taunt and tease and riff off each other like they've been playing dress-up together their entire lives. Without missing a beat, Alvarez dubs Groff's impish attitude "hashtag chapswag," and the nickname sticks. The show's creators and many of the crew are queer, but you'd need a cheat sheet to remember who's not actually gay (Castillo and Alvarez, if you must keep score).

When they're not filming in a Bay Area bubble, Groff says, most of the Looking guys live in New York. "Last year, I saw Frankie and Murray at least once a week," Groff says. He and Castillo sometimes spend all day acting together, then go out to see a movie the same night. On-screen, their sophomore season will be packed with more early-adulthood existential crises and tangled relationships -- but at a more fevered pitch. "The show took its time to set up the characters and story lines last year," Groff says. "This season moves at a faster pace. A lot happens quickly."

*Straight actors Raul Castillo and Frankie J. Alvarez didn't rank among our LGBT-only Out100, but we love them anyway.

Shot at the Phoenix Hotel, San Francisco on September 11, 2014

Styling by Kiersten Stevens. Groomer: Ivan Mendoza, both at Workgroup Ltd. All leather available at Mr. S, San Francisco. Tank top available at Wasteland, SF (Groff). Shirt available at Wasteland, SF (Alvarez)

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