How Sexyy Red Is Rewriting Rap’s Playbook: ‘People Think I’m Crazy But I’m Just Myself’

Sexyy Red isn’t concerned with chasing hits. “I’m not even trying,” she tells Billboard over Zoom. “You just gotta be yourself and then they gonna f–k with you.” 

She’s living proof: the 25-year-old (born Janae Wherry) is currently enjoying a breakout year thanks to her sexually explicit, Tay Keith-produced “Pound Town.” Since the trap single arrived in January, Sexyy Red has formed bonds with some of R&B and hip-hop’s biggest names, befriending Travis Scott and Drake (the latter has posted a picture with her on Instagram, and Sexyy Red has teased music together), and collaborating with Summer Walker and Nicki Minaj.

Her “Pound Town 2” remix with Minaj dropped in late May and became Sexyy Red’s first entry on the Billboard Hot 100 the following month, debuting at No. 66. Still, she remains blasé toward her A-list interactions. “I already know I’m a cool, f–k-witable person,” she says.

It’s not surprising that the St. Louis native has maintained her nonchalant attitude amid her rise. After all, it’s what helped put her on the map: According to co-manager Caprie Poe — who is also general manager at Miami-based label Rebel Music — Sexyy Red first caught the attention of an A&R rep at the label in 2021 with her 2018 single “Free Smoke.” “[She] was super raw and authentic,” says Poe. “She always says what’s on her mind.” Case in point: the “Pound Town” lyric that has taken the internet by storm (“I’m out of town, thuggin’ with my rounds/My c–chie pink, my booty h–e brown”).

The rapper signed to Rebel Music and released her debut project, Ghetto Superstar, that December to local acclaim. But co-manager and Rebel Music founder/CEO Javier “Jay” Sang says the team was dedicated to growing her national audience: “We treat Sexyy Red as a 24-hour, seven-days-a-week business.”

Their strategy paid off last fall, when they encouraged Sexyy Red to follow up with Tay Keith (who she was acquainted with), leading the Grammy-nominated producer to send her the beat to what became “Pound Town.” Soon after, she was freestyling about a sexcapade with an ex-boyfriend during a Miami studio session. She remembers laughing with her friends throughout — but her team was more earnest. “They was like, ‘You playing on this man’s beat,’” she says. “I’m like, ‘Ain’t nobody trying to be serious all the time.’ Finally, they [said], ‘I understand your vision.’” 

By February, she released a music video inspired by the reality show Cheaters, followed by a Miami spring break edition of the clip in March. The track has also found success on TikTok having been used in over 250,000 clips. There’s even a mashup of the song called “Frontin’ x Pound Town Simmy Mix,” where Chicago native DJ Simmy overlaid Red’s vocals on Pharrell and Jay-Z’s “Frontin’” beat. But the original song needed a final push to become a hit.

Around the same time, industry veteran Larry Jackson launched Gamma — a media company specializing in distribution, creative guidance, marketing and more — and signed Sexyy Red while building a roster that includes Snoop Dogg and Usher. (Sexyy Red also remains signed to Rebel Music.) “She immediately became a priority,” says Sang. “I know Larry for moving mountains and he was like, ‘What do you think about Nicki on the record?’ It was a no-brainer.”

As the song continues to grow, Sexyy Red knows that it’ll “never get old,” but is ready for people to start focusing on her other music. “SkeeYee,” another Tay Keith-produced track — and popular greeting call in St. Louis — on her June mixtape Hood Hottest Princess, has been gaining momentum of late.

This summer has also included a Rolling Loud performance, and soon, a few opening slots for Moneybagg Yo on tour. She’ll eventually embark on her first headlining trek, with dates and locations yet to be announced, but for now, she’s letting her team handle her business affairs. “I’m just the artist and they do what they do to make it happen for me,” she admits. “They ain’t trying to stress me out because I don’t even want to deal with no s–t like that.”

Instead, she’s focusing on what she does best: releasing one salacious, unapologetic song at a time, she says. “People think I’m crazy, but I feel like I’m just myself.”

A version of this story will appear in the Aug. 5, 2023, issue of Billboard.