A short stroll from the glitz of San Francisco’s beating heart of tourism, Union Square, lies the Tenderloin, a neighborhood that was once the epicenter of vice, sex, jazz, immigration, and the early days of gay culture. At a time when SF experiences a hyperdrive tech-fueled boom, the Tenderloin remains its gritty, defiant self — true to its roots, for better or worse.

Aunt Charlie’s holds the dubious reputation of being the last gay bar in the Tenderloin, an area once home to the largest concentration of them in San Francisco, preceding even the Castro.

A look behind the curtain at this institution shows that Aunt Charlie’s is much more than its “last” designation — it’s a sacred throwback to San Francisco’s past in a city quickly gentrifying around it. As someone who grew up nearby on Sixth Street, I was always fascinated with the bar, and had my share of hazy nights there. When two other longtime Tenderloin gay bars, the Gangway and Divas, closed in recent years, I reflected on Aunt Charlie’s significance and wanted to document it. Over the span of several months, I dropped by Aunt Charlie’s to enjoy some drinks, chat it up with the girls, and take some photos. The visits provided insight on the bar itself — but even more interesting, on the personal backgrounds of the performers.

Aunt Charlie’s has lived several lives, originally dubbed Mitch’s as it served as a bar for merchant seamen passing through SF. In the 1970s, it transitioned into a gay bar called the Queen Mary, and then Aunt Charlie’s in 1987 when it was purchased by Bill Erkelens, a local who owned other dives in the area. In the late 1990s, as the neighborhood began to change and other gay bars closed, Aunt Charlie’s began hosting drag shows. Erkelens, who identifies as a straight man, moonlights as a crossdresser, and the shows allowed him to not be the only man dressed in women’s clothing in his own bar.

The name Aunt Charlie’s comes from the original manager, Charles (also known as Chuck) who worked with Erkelens for 20 years.

“Back then, there were a lot of hustlers in the area, so Chuck had a lot of ‘nephews.’ He knew a lot of the boys,” said Joe Mattheisen, who’s been the surly bar manager and gatekeeper of libations since 1997.

Every weekend, the Hot Boxxx Girls, adorned in a flurry of over-the-top wigs, jewelry, gowns, and expertly applied and wonderfully tacky makeup, make the audience blush. They put on a show of singalong classics from yesteryear, current Top 40 hits, and some original tunes; and these queens know how to work the room. The crowds are a mixed bag: birthdays, elder gays, bachelorette parties, couples, young queers, and the wayward tourists who somehow ended up here.