When Lanny Swerdlow opened Portland's only all-ages gay nightclub back in the late '70s, he figured he was doing the city a favor. The only place for young gay people to congregate at the time was the cruising spot on the corner of Southwest 3rd and Yamhill. After Swerdlow established his club, the cruising spot cleared out practically overnight.

Instead of receiving a medal of commendation, Swerdlow was vilified. He was accused of indoctrinating teens into the homosexual lifestyle and hounded by church groups. The worst thing he did, though, was undercut the Police Bureau's ability to bust kids for curfew violations.

"That began the war between me and the cops," Swerdlow says.

The conflict would play out over the next two decades, in several different locations and iterations and it would culminate in a protest march to City Hall. In 1989, Swerdlow moved the club, by then called the City, into a warehouse in the pre-Pearl District, and began drawing crowds of 2,000 on weekends. Swerdlow enjoyed antagonizing the authorities: He ran TV ads boasting of "violating traditional family values" and sold shirts declaring "I Had Sex in the Bathroom of the City Nightclub." But for regulars, the club wasn't just a staging area for wild nights out. It's where they learned to feel comfortable in their own skin.

"I longed for the weekends so I could escape to the city, to see and meet more fun, young, alive people, gay youth my own age," says Kevin Cook, known in the Portland drag community as Poison Waters. "I craved it: the dark club, the pulsing beat of the music, the stench of clove cigarettes—all of it. The club represented my rebirth."

At its height of popularity, the City was the focus of constant police scrutiny, under the pretext of pervasive drug use on the property. In 1996, the city attempted to use its drug-house ordinance to shut down the club. On March 18, nearly 500 supporters marched from the club to City Hall, waving signs and chanting, "Save the City!" Even MTV covered the protest.

By year's end, though, Swerdlow was too exhausted, financially and mentally. He closed the City and later moved to Palm Springs. Today, the club has faded as an icon of Old Portland. But for those who were empowered by those nights on its dance floor, and politicized by the battle to keep the doors open, the club's legacy is part of them.

“I can’t imagine my life without the experiences of the City nightclub,” Cook says. “My life is exciting and plentiful, and I doubt it would be such had I not walked into that club almost 30 years ago.”

From the Archives:

"In the City", August 27, 2014: A ten-year retrospective on the City Nightclub closing