Some gigs go by in the blink of an eye. At midnight on June 14, a drag queen parted the crowd at Produce Row and took the floor, running around screaming before dropping into a split. By the time her act was over, I assumed I’d somehow missed part of it. “That’s all I’m doing tonight,” she told me after. “I got paid to show up for an hour just to be in drag and say ‘DRINK!’” The queen noted my camera and turned to a stranger. “He’s writing an exposé,” she said. “I’ve got to be on my best behavior.” Moments later, the queen and the stranger were making out.

Silhouette, a 26-year-old drag performer from Clackamas, is not an alumnus of RuPaul’s Drag Race. She carries her wigs in a tiny toy suitcase. Her signature mustache—as much a calling card as it is a self-imposed obstacle—boosts her out-of-drag masculinity and slices through the illusion of in-drag femininity. Her makeup glimmers with sweat on a hot night, threatening to reveal the true jawline underneath. “I wish I was better at my nails,” she said after another show the following week, a tiny electric fan working overtime to keep her beat in place. “This is how a real woman’s hands look,” she went on, holding up her non-manicure. “A real working woman.”

Work she does. It was June after all, the hustle month for drag queens—and anyone who makes their living doing something explicitly queer. Though not without its benefits, the aggressive seasonal allyship of Pride month puts the queer entertainment scene in a vacuum. For many, Pride is the only time of year large-scale or straight-owned businesses invest in queer art or entertainment; as such, there’s a pressure to pack a year’s worth of entertainment, art, and income into a single month.

But it’s getting harder to predict in Portland. Since 2023, when Portland’s official Pride festival and parade shifted to late July for logistical reasons, June has been in a state of limbo. All the more reason to push for what you’re worth, says Silhouette, who often books two gigs per night during Pride. She has no qualms with making a business of her drag. And she’s laying a path for others to do the same.

A self-titled “girl’s girl,” Silhouette is a people’s drag queen. She talks with just about everyone she sees in an evening. While you may not look at her and immediately scream “MOTHER!!!!” you get the sense she’s at least a cool aunt. She’d let you hit her vape pen and not tell your mom. And she’s thus become a community pillar, both a performer and event producer helping to grow the local scene through this nebulous, transitional time. “I have my place,” she says, “not just as a drag queen, but as a community member.”

“They’re just a real breath of fresh air,” says Katya Butler, a queer nightlife stalwart whose production company Klip Klop specializes in drag-focused dance parties. “They do a lot of work making sure people get gigs, get well-paid gigs, and get treated fairly at the gigs—just consistently thinking about the artists.” Drag shows around Portland can involve everything from comedy to hosting bingo, burlesque to lip-syncing Sabrina Carpenter—as Silhouette did at a recent show at the Triple Nickel Pub. Pride doesn’t necessarily mean performers are getting paid more, but it does widen the scope of opportunities, bringing drag to venues across the city for the season. At least historically.

This June was particularly tough. Organizers waffled over whether to celebrate Pride alongside the rest of the world or hold out for July. A summer equinox party Silhouette helped produce started strong, but the crowd dropped off around 1am; they were expected to rage through 4am. “The vibe was never not fun!” Silhouette said. But it didn’t feel like Pride. The third anniversary of Trans-UHH-Licious, a trans and nonbinary drag event at CC Slaughters, was also poorly attended. “That was disappointing on a community level,” Silhouette says. And June attendance of her own monthly brunch show at Sad Valley didn’t see a spike.

Performing at a Goose Hollow mansion for a real estate firm’s Pride party was a different story. Silhouette gets more corporate gigs like this during Pride month, when organizations otherwise disengaged from queer life make their annual attempts at allyship. But these events present their own set of issues. “You don’t know how everyone’s gonna feel about a drag queen,” Silhouette says. “Sometimes, the one queer person in the room booked the drag queen and it’s just a bunch of straight people being, like, ‘Yay…? I guess?’” That wasn’t the case here. Silhouette and her two fellow queens brought home $300 in tips.

In a more direct approach to bringing corporate money into the community, Silhouette is co-producing Dollapalooza 3000 with Butler, a weekend-long bender of a drag-a-thon. Butler’s connections helped score a major sponsorship from ad agency Wieden+Kennedy, which helped book Drag Race alumni Anetra, Mirage, Olivia Lux, and Willam. They’re selling tickets on a sliding scale ($25–50) in an effort to maximize profits while preventing the party from exclusively catering to wealthy queers, a common pitfall of events with high-profile headliners. This also helped raise rates for the 60 queens performing to $150 per number, in line with Silhouette’s own rate, double what she calls “Portland’s minimum wage for drag performance.”

“Talking to people is part of the gig,” Silhouette says. Finding new ways to fund events, including navigating corporate structures, is part of what makes her successful in a community-based art form. She talks with that same radiant confidence she projects on stage. Much of which seems borne out of not fitting the stereotypical drag queen mold, a struggle that she and her mustache constantly face, but more so during Pride, when seasonal audiences bring their clichéd expectations to shows. “Polished drag queens are a dime a dozen with the YouTube generation,” she says. “You have to be more than that.” For Silhouette, “more” clearly stretches past the stage. “They’re at your show. They are yelling. They are tipping,” says Butler of Silhouette. “If you need help, all of a sudden, they’re there.”