“The first thing we do when we book: we type in your name, and we write ‘homophobic,’” says nightlife promoter and producer Rayne Baron of finding acts for her annual festival, LadyLand. If nothing incriminating shows up, the artist has “passed the first test.” Next up: Has the musician in question wished fans “happy Pride”; have they collaborated with LGBTQ artists before; have they ever just flat-out said, “I love gay people”?

Sitting in Greenpoint’s quaint McGolrick Park as a light rainstorm hovers above, Baron — better known to New York City music venues and party people as Ladyfag — is telling Billboard how she and her tiny team go about booking acts for her LGBTQ music festival, which debuted in 2018. Baron is laughing, but she’s entirely serious: LadyLand is a very queer and very Brooklyn affair that takes place during Pride Month — a time when the last thing any self-respecting LGBTQ person wants to do is watch a hater, or even a lukewarm ally, onstage.

Over the course of seven years (during which it took a pandemic breather), LadyLand has grown from a 5,000-strong party at Bushwick’s Brooklyn Mirage to one with 10,000 revelers at Greenpoint’s Under the K Bridge Park, the fest’s home since 2023; this year, LadyLand is expected to draw some 20,000 to the official-but-DIY-coded outdoor space on June 27-28, with Cardi B and FKA Twigs headlining.

“It’s not a party with problems,” she muses of the event, which takes her three-person team all year to plan. “It is a problem, and you keep solving them until you have a festival.”

2025 marks her second year working with Bowery Presents on LadyLand, which they co-produce. “It was a struggle from the start to find investors,” she admits. “People said the numbers don’t work, there’s a reason it doesn’t exist.”

But Baron — who by the time LadyLand launched in 2018 was an NYC nightlife legend thanks to seamlessly executed ongoing parties like Holy Mountain and Battle Hymn — was undeterred, intuitively sensing that queer New Yorkers, Brooklyn residents in particular, could use something that was “part party, part concert, part festival, part gay Pride.” LadyLand has been called “gay Coachella,” a label that Baron embraces while noting that it doesn’t quite give the full scope of the experience. (“But that’s fine, because people need something to reference,” she says.)

While Coachella brings to mind influencers snapping selfies in the desert, LadyLand is an inner-city gathering for LGBTQ people whose very identity reshapes culture — not merely reposting or recreating it after it’s made the rounds.

“In Brooklyn, we are still the heart of queer counterculture. We still write the prophecies for fashion, our DJs are playing the tracks with the ripple effect and the slang we use is a solid three years ahead of Hollywood,” says Charlene, a local performer and writer who’s become a mainstay of Brooklyn’s queer scene over the last decade (she recently took over summer Sunday BBQs at long-running gay bar Metropolitan from “Mother of Brooklyn Drag” Merrie Cherry.) “LadyLand is the only festival in New York that happily places our club fixtures and family alongside acts that are frankly too big for the club.”

“What makes LadyLand stand apart is how it celebrates the full spectrum of queer creativity — New York DJs, underground legends, dancers, fashion kids — it’s all there,” says dance music and ball culture legend Kevin Aviance, who made a surprise appearance in 2019 and returns this year. “Ladyfag curates with such intention, and it shows. Unlike circuit parties, this isn’t just about a beat — it’s about art, community and freedom.” As for what to expect from his DJ set, he adds, “Get ready, because I’m bringing the heat. Beats will be served, and the dolls will dance.”

That club-meets-festival vibe means that despite LadyLand’s big headcount, it doesn’t feel like a sprawling, isolating affair. “If it’s 10,000 people, 5,000 of them know the other 5,000; if they don’t know them, they might want to sleep with them. So you have to make it feel more familiar,” Baron says of pulling together the three-stage festival every year. “It’s a really strange concept to explain [to investors].”

Baron says Bowery Presents (which owns and operates many NYC venues) has been an open-minded co-producer. “It’s nice to feel supported,” she says. “They’re concert people, they know.” She also hails 12-year partner Red Bull: “They don’t do bullsh-t. They have never tried to do things that would affect the integrity of LadyLand.” This year, the energy drink brand helped her create a new stage that will bring Paul’s Dolls, a weekly party in Manhattan celebrating trans artistry, to the fest. “It’s a club, and you cannot have a gay club without dolls. We need them they need us. Gay culture is an ecosystem,” Baron explains. “In general, gays to the front. You don’t have to be gay to be here, but it helps.”

Ladyfag took her signature festival (including those giant inflatable green forearms with blazing red nails) from the Brooklyn Mirage to Under the K Bridge in 2023 for a simple reason. “Mirage kicked me out because I didn’t make enough money,” she frankly admits. When she started looking around her own neighborhood of Greenpoint, she was struck by the fact that the freshly built state park (where folks sometimes held illegal raves during the pandemic) reminded her of an electronic music festival in London which takes place in a park under a bridge. “I was always obsessed with Junction 2 Festival — my wife is English,” she says. After connecting with the parks department, she pulled everything together (“shoutout to my little team, Veronica and Carlos”) in just three months, putting on the first big event of any kind at the Under the K Bridge Park: “There was no template.” Since then, the state park has hosted numerous live music events, with the inaugural CBGB Festival set to take place there on Sept. 27.

To appeal to an extremely discerning nightlife crowd (“people can be c-nty,” she sighs) and live music lovers in a city that has no shortage of concerts, Baron goes through a high-wire balancing act every year while booking the lineup. Her team needs to nab headliners who sell tickets, but not book so many A-listers that it turns into a gathering of Stan armies. “I don’t want mega fandom,” she says. “We don’t want people standing in front of stage for 20 minutes waiting for the next performer, ruining the vibe.” She mixes in LGBTQ legends with up-and-coming artists, and spotlights local talent while also bringing in names who rarely make it to NYC. Plus, there are radius clauses with other NYC events and scheduling conflicts — oddly enough, Glastonbury has proved to be some of her biggest competition simply because it often goes down the same weekend and can pay more to performers than her scrappy little fest can.

“We are a small festival, as far as fests go,” she acknowledges. “Agents’ jobs are to make their artists money and there have been a lot of kindnesses shown my way.” Her long history in NYC nightlife has helped in that area, too — including for this year’s day-one headliner. Prior to Cardi B’s meteoric rise, when she was just another reality star (Love & Hip Hop) trying to break into music, Ladyfag booked her to play her monthly party Holy Mountain in February 2017. “She got very excited about being with the gays,” Baron recalls, her lips curving and eyes twinkling. “She was only supposed to do a few songs, but she wouldn’t stop. Within a few months, she became one of the biggest stars in the world — and she always remembered it.”

With that shared history, Baron was able to get the hip-hop superstar for less than what Cardi B would get from Madison Square Garden. “Was it free? F–k no,” she laughs. “Was it $4,000 that she put in her bra back in the day? No, we have all evolved from that.” This year’s day-two headliner, FKA Twigs, is someone Baron knows “outside of her agent,” too. LadyLand’s 2018 headliner Eve came from a similar situation (“We met at a party”) and she notes that while the inaugural edition “didn’t make any money, we didn’t lose money.” The following year, her nightlife background helped her nab Pabllo Vittar to pinch hit at LadyLand when headliner Gossip dropped out the last minute.

“We jumped in blind not really knowing what to expect, but I was completely blown away,” says the Brazilian drag juggernaut, who returns to play the fest this year. “It was amazing! The community, the energy, the artists, the vibe. I am so honored she asked me to play again this year officially, it feels very full circle with her.”

Despite that extensive Rolodex, LadyLand now books dozens of acts each year — meaning long gone are the days when everyone on the bill is a pal or acquaintance.

To fill out the lineup — and bring in artists outside the NYC nightlife realm — Baron and her team spend months sending each other clips of singers, DJs and rappers, debating their musical merits and keeping an eye on who’s buzzing on queer socials. Oftentimes, that means she can book rising artists before they become big names and demand higher price tags. One such case was 070 Shake, who blew up after signing on for the inaugural LadyLand but before the festival made its bow; this year, she sees 19-year-old rapper Cortisa Star in that vein.

But intuition without dollars only goes so far. With palpable remorse, she talks about the year where she almost booked a pre-fame Megan Thee Stallion but wasn’t able to afford the private plane that would have been required to take the rapper from point A to point B. Miley Cyrus has been a white whale for LadyLand; she says they’ve tried to get Ethel Cain every year; Grace Jones is on her wish list; and once she almost had Charli xcx locked, but her stage setup was too large for LadyLand’s then-home at Brooklyn Mirage. “Those are the things that happen that people don’t understand,” Baron says ruefully. But with each passing year, she checks another name off her wish list. For 2025, that “bucket list” booking was New York dance legend Danny Tenaglia, who plays Friday, the same day as Cobrah and Sukihana.

Plus, there are leftfield surprises that seem to fall into her lap thanks to LadyLand’s reputation as an experience that is queerer, edgier and more communal than most Pride Month events. “I appreciate those people who don’t need me and did it anyways. Madonna doesn’t need me, she had just done Brazil — the biggest concert she’d ever done — and then she came to my festival,” Baron shares of the 2024 edition, where the Queen of Pop popped by to help judge a ball. “She wanted to make a moment for gay people, and she did.”

Her careful, intuitive curation has brought everyone from SOPHIE to Honey Dijon to Pussy Riot to Christina Aguilera to the LadyLand lineup. “For a lot of people, it was the only time they ever got to see SOPHIE,” Baron says. One of those in attendance at the late electronic pioneer’s 2018 set was indie singer-songwriter Liam Benzvi, who is on this year’s bill. “The BQE is an institution of noise, and I’m proud to call it a friend and a bandmate,” says Benzvi of delivering his synth-pop gems at a state park that is literally under the Brooklyn-Queens Expressway. “Being from Brooklyn, I expect to see quality live music while surrounded by cool people, and cool is usually LGBTQ, so it’s a win-win for me.”

Bringing thousands of people to a state park entails “so much more work,” Baron chuckles as the raincloud above us finally burst open, forcing us to move the interview indoors to her apartment. “It’s a neighborhood. People live here — I live here — and you can’t have people partying after until 7 a.m. We need to make sure there’s enough bathrooms so that people aren’t pissing everywhere…. These are things that people don’t think about, nor should they have to.”

Plus, there’s “boring festival stuff with agents and managers, arguing about the run of the show, the size of the name on the poster.” To ensure each day’s lineup has an organic flow and isn’t solely based on least-to-most Instagram followers, there’s oftentimes an extended back-and-forth with artist reps, who care less about sonic juxtaposition and more about optics. “Sometimes agents do win and it’s a pisser,” she says. “I’m usually right on vibes.”

As anyone who has spent a moment at LadyLand (or any of her ongoing parties) can attest, Ladyfag does indeed know vibes — arguably, she’s become the premier connoisseur of queer nightlife vibes in NYC over the last decade. And in doing so, she’s not only spotlighting queer culture, but changing it.

“Ladyfag has created the pinnacle opportunity for us to show off the cultural engine we are,” Charlene says, “and in doing so has reshaped my relationship to the word ‘Pride.’”

“It feels like church for the children, honey,” says Aviance. “A safe, fierce space where you’re seen, heard and celebrated. I’ve been to a lot of parties in my time, but LadyLand is truly one of the best.”