Tabby Wakes likes to troll people. When we meet at one of Lower Manhattan’s busiest intersections in September, the 23-year-old rapper and entrepreneur is wearing a Demi Lovato, DJ Khaled and Kehlani tour tee. “I think it’s hilarious,” she says, in awe of the merch while admitting she hadn’t actually attended the concert. Plans had changed and instead of checking out the music studio she owns and operates in Ridgewood, we decided to meet at her “other office” downtown, which turned out to be a CBD pop-up shop on Canal Street (she and her friends work there). There’s a new Vietnamese café she knows about and on our walk over, Tabby points out plots of pavement where she recalls popular street vendors getting shut down by the police. It’s a moment from our conversation that stands out, not just as anecdotal evidence of Tabby’s experience as a lifelong New Yorker, but as a window into the earnestness behind her “trolling” ways.
“‘Congratulations’ is like a play on society,” Tabby says of the opening track on Over Night, her EP out this year via A-Trak-founded label Fool’s Gold. “People will be like, ‘Congratulations,’ and you’re like, ‘I mean, I guess’”—she shrugs. In person, Tabby exudes the cool nonchalance she expresses on the song, from her skater lingo to the casual mention that when she’s not making music or working on a rebrand of her recording studio, she’s hosting parties at the notorious strip club Sapphire on 60th Street. Spending time in New York City, particularly Manhattan, can be unrelenting, and sometimes, you’re too busy hustling to reflect on the progress you’ve made. Tabby was in middle school when her family moved from Crown Heights to Midtown, and into a very different, fast-paced physical and cultural experience. “I moved back to Brooklyn [recently] and it was just so slow, it made me chill way harder, and I was like, ‘damn, I need to not feel that comfortable,’” she says, touching on her mission to work as hard as she can for as long as she can. 
Tabby is a proud ’90s baby, citing Mariah Carey, Lady Gaga, Mary J. Blige, Alicia Keys, Missy Elliott, Jay-Z and Busta Rhymes as essential to her musical foundation. In college at Stony Brook University in Long Island, Tabby formed a rap group called Holy Tower with two friends and started recording. The collective fizzled out, but, in 2018, she signed to Fool’s Gold and got to work on putting together what would become the melodic, hip-hop/pop hybrid oeuvre that she showcases on Over Night. With the support of her community, she also launched Blahkwork Studios, aiming to create an accessible environment for other local young artists to build a foundation for themselves. “Let’s say you’re an engineer and you don’t have clients, right? I’m trying to make a stepping stone—you start working out of this space and get more and more clients, and then you can start your own studio,” she shares.
Some of Tabby’s songs further reveal her playful side. On “Snakes,” a candy-sweet bop she imagined for kids, and “Lady Gaga,” which she says she “geeked out” making, Tabby’s buoyant energy flows through glistening, auto-tuned vocals and hypnotic, twerk- inducing chanting (“I’ve gotten some videos [sent] to my phone,” she adds). More sobering are the stories she tells with her music. “I feel like when I made it, I didn’t even understand what it meant,” she admits about “Angel,” an ominous-sounding track whose prophetic, intimate lyrics later came true in a personal relationship. Her artistic process is varied, as intuitive and silly as it is earnest and measured. She recorded much of Over Night in Miami, where she locked in with the producer Brenmar, thanks to label head A-Trak. Elsewhere on Over Night, production from New York’s beloved underground hip-hop producer Tony Seltzer cruises below Tabby’s twinkling hooks.
Tabby has a tattoo on one arm that reads “over night.” She explains that the ink and matching EP title are also her poking fun: “Literally nothing happens overnight, no matter what you think— even if you’re talking about viral hits, it’s like, that did not happen in a day.” For Tabby, this chapter is just the beginning. Though she acknowledges that it’s a turning point, she’s feeling “chill” about her debut EP being out in the world, always looking ahead to what’s next. “I’m looking forward to putting together my next project. I kind of want to go to Tokyo or something, just to feel inspiration,” she says, sharing little on those plans other than a gut check. When I instinctively congratulate her on the year she’s had before we part ways, we both laugh as she says—“I knew you’d do that.”
