New York’s cultural scene has had an exciting week. After Monday’s Met Gala, Frieze New York launched yesterday at The Shed, featuring around 65 top galleries from over 20 countries. While that’s impressive, it’s the hidden gems that truly stand out.

One such gem is Midtown by New York legend Tabboo!—a multitalented artist known for his work in the gay community. The piece, part of Karma gallery’s showcase at Frieze, belongs to his Cityscape series, capturing New York skylines in dreamy shades of blue. “People like blue paintings,” Tabboo! (born Stephen Tashjian) remarked in a phone call before the fair, his voice carrying a hint of melancholy. “They can live with blue.”

Though he was referring to interior design, Tabboo! has always had a gift for distilling collective emotions into simple truths. Life can be chaotic, and feeling blue is inevitable—but we learn to live with it, just as he has.

Tabboo! adopted his stage name when he entered the drag scene in the ’80s. While he’s now celebrated for his evocative cityscapes that capture New York in all its seasons, his earlier work—illustrations for magazines like Interview and album covers for artists like Deee-Lite—made him a queer icon. His performances as a go-go boy and drag artist at legendary spots like Palladium and Pyramid Club further cemented his status.

Earlier this year, while visiting friends in Hudson, New York (a growing gay enclave), we watched Wigstock: The Movie, a 1995 documentary about the iconic drag festival. The film features performances by RuPaul, Deee-Lite, Debbie Harry, and Tabboo!, among others. For many in our group, it was a first-time viewing—a glimpse into the joys and struggles of queer life in the ’80s and ’90s, when AIDS devastated the community. Today, with PrEP and greater visibility, the urgency of that era feels distant, even as our rights face new threats.

Days after watching the film, I found myself at Karma gallery in the East Village, standing before a Wigstock backdrop from 1990. Tabboo! was there, ready to guide me through Early Works, an exhibition of his pre-fame art. When I asked about the documentary, he laughed: “I heard Hollywood was coming, and I thought they’d take our underground drag scene global. I performed ‘Natural’ because I figured they wouldn’t get all these men in dresses. And now, years later, it’s all ended up in a New York gallery!”

The show highlights his illustrations and paintings from before his current success. “Not that it’s not about my art,” Tabboo! said, “but this show is really about…” [text cuts off]”That whole culture doesn’t really exist anymore,” he says. “And it might not come back for another 20 years—especially with the whole Trump era. I’m glad this show opened before he became president.”

Tabboo!’s stories and Early Works made two things clear to me: First, we live in a completely different world—and a very different New York—from the one Tabboo! first made his mark in. Second, my generation should do more to protect our community and learn about those who came before us.

One of Tabboo!’s first friends in New York was Jean-Michel Basquiat, who appeared in his work alongside other icons like Keith Haring and RuPaul. Tabboo! moved to the city about 40 years ago and has lived in the East Village ever since. He’s been a muse to Nan Goldin and Peter Hujar. Simply put, he’s a vital part of the queer New York that people my age often romanticize—yet he isn’t as widely recognized today as the other names mentioned here.

A born performer, Tabboo! started creating puppet shows as a teenager. When he arrived in New York, the art scene was thriving but still divided. “I could be myself in gay clubs and in drag,” he says. “It paid, and back then, it was the easiest way to get on stage.”

The reason Tabboo! isn’t as synonymous with gay culture today as, say, RuPaul, might be because he’s lived many lives over the past four decades. He no longer does drag, having shifted his focus to painting—something he’s done quietly since the ’80s. The only remnant of his performance career is his name: “I was told I needed a drag name because ‘Stephen’ wouldn’t cut it on stage. Being gay was taboo, and my aunt’s stage name was ‘Boo,’ so I combined them and added an exclamation mark—very showbiz at the time.”

Much of Tabboo!’s art follows the same logic—a mix of instinct and necessity, fueled by raw creativity. Those legendary hand-drawn posters for his performances? “We needed posters,” he shrugs. His later paintings, featuring everything from soup cans to doll heads to Jayne Mansfield cutouts, were simply “what was in front of me and what I had.” Yet his visual style became a defining snapshot of his era—a grittier New York where people like Tabboo! could not just survive, but thrive. His posters captured gay life then: Barbra Streisand lip-syncs, makeshift drag outfits, and my favorite—a muscular man as “body” and a cartoonish drag figure as “soul.”

“I always drew hairy chests and Adam’s apples,” Tabboo! laughs. “Back then, everyone was trying to look real and fierce, but I drew it in this exaggerated, comic way. Now people might call it transphobic, but it was an inside joke—our joke.”

Language was simpler then, less nuanced. Today, we have more ways to express ourselves and define our identities—which Tabboo! and I agree is a good thing. But he wonders if younger generations realize any of this history existed. “I know you all watch Drag Race…”He mentions the popular reality show Drag Race, then asks, “But do your friends know about this New York?” I tell him they do, in theory, though not all of them know the gritty details. He brings up shows like Pose, which captured the Ballroom scene of the ’80s and ’90s, as the kind of media we need more of—aware of how younger generations learn through entertainment.

Tabboo!, after decades in the scene, is finally gaining mainstream recognition (and financial success) with his paintings. They’ve always been part of his work, but now they’re what people mention first. He’s enjoying the wider appreciation and the stability it brings. Fashion has always been a passion, and now he can afford it—when we met, he was wearing Bottega Veneta and Dries Van Noten. Back in 2016, Marc Jacobs collaborated with him, and it wouldn’t be surprising if another brand reached out soon.

A week before our talk at Karma, actress Hunter Schafer went viral after posting about her passport listing her gender as male, criticizing the new U.S. administration’s narrow view on gender. (Schafer is trans.) She later appeared as a guest judge on Drag Race while the internet debated her identity. “All the things we fought against,” Tabboo! says, as if summoning the people in his art, “are coming back, don’t you think?” I agree—it certainly feels that way. “But your generation isn’t as rebellious, is it?” he presses. Sometimes, I say. I’d like to think we are, but we’re also products of the internet, of Instagram activism. Still, there’s plenty to protest now. “Maybe this will wake people up,” Tabboo! says, hopeful. “Maybe it’ll bring that New York back.”

When AIDS comes up—as it often does in conversations between gay generations—Tabboo! reminds me, “This was during the worst of it, when people said gay men should die. But those still alive kept going, building communities through Voguing, Wigstock, everything.” He asks if my generation truly understands how bad it was. Sort of, I say. We have PrEP now, and queerness is more visible, but the internet struggles with history and nuance. “They should know,” he adds. “When I was young, nothing was out in the open—we had to dig for it. So many are gone, but I’m still here.”