Lil Skies: SoundCloud Rap Gets Its Small-Town Success Story

Lil Skies: SoundCloud Rap Gets Its Small-Town Success Story

Nicholas Jandora

The streaming sensation putting Waynesboro, Pennsylvania on the hip-hop map

The streaming sensation putting Waynesboro, Pennsylvania on the hip-hop map

"There was no rappers," 19-year-old Lil Skies says about growing up Waynesboro, Pennsylvania, a small town tucked away near the state's southern border with Maryland. "People listen to rap some, but it's a lot of country and shit. They're more in tune now."

Lil Skies has amassed an impressive following on SoundCloud despite growing up in such an unlikely hip-hop locale. Last week, his songs "Red Roses," "Nowadays" and "Creeping" were three of the Top 20 most-streamed songs on the platform. His songs are repetitive, punchy and melodic, mixing a teen's me-against-the-world angst with hip-hop bravado, the lo-fi rants of SoundCloud rap with smooth singing. In turn both "Red Roses" and "Nowadays" hit the Hot 100, and Lil Skies eventually inked a deal with Atlantic Records, 2017's top label in terms of overall chart performance.


Due to his recent success, the rapper has been ping-ponging around the county, promoting his own work and opening shows for Lil Uzi Vert. On a cold night in February before he made an appearance at New York Fashion Week, Skies sat in a hotel room near midtown Manhattan in a shiny blue Adidas sweat suit, toying with one of his thin red braids as re-runs of The Office played on the television. "I can come here, but I wouldn't live here," he said of New York. "It's too congested; everybody on top of each other. I like back roads and shit." L.A. doesn't do it for him either. "Cali just be so nice all the time; I hate that shit," he declared. "How you wake up every day and it's just nice? I can't experience no moods."

Though there's no musical infrastructure in Waynesboro, Skies had an example of aspiring rapper-dom close to home: His father had tried his hand at a career in hip-hop. As a result, Skies says, "I've been in the studio environment since I was young, so I know what to expect." He was selling his own mixtapes around school at age 10. "I was very hands on – put the cover in the CD case, sign 'em," he remembers. "I made like 50 copies. I sold 'em all in the first day or two."

Jeff Vaughn, the A&R who signed Lil Skies to Atlantic, believes the rapper's Waynesboro background is an important part of his appeal. "I loved the fact that he was from Pennsylvania, and not from a Pennsylvania that you and I had ever heard of," Vaughn says. "I think people are identifying with the fact that he's a small-town kid, with that story of coming from where there's not a lot to do and all you have is your imagination, your music."

Lil Skies was also savvy about using the internet to neutralize any geographical disadvantages he faced, migrating to SoundCloud and connecting with influential figures on YouTube. Watching a vlog from YouTube crew Cufboys – their channel has over 700,000 subscribers – Lil Skies happened to hear the group's Landon Cube playing one of his songs. He reached out and befriended Cube and the other Cufboys, including booster Cameron Haller.

"[Haller] was putting me in his vlogs – he had a nice platform, and he was like, 'Go fuck with the kid,'" Lil Skies explains. Cube sang on both "Red Roses" and "Nowadays," adding winning melodies that might entice listeners outside of the world of SoundCloud. And through Cube, Lil Skies also met the director Cole Bennett, who has helmed popular clips for SoundCloud stars like Lil Xan and Lil Pump. Bennett subsequently directed the videos for Lil Skies' two hits.

Now that his 2017 mixtape Life of a Dark Rose is a success, the rapper will head out on his own headlining tour. He's already developed a reputation as a live-wire performer: Vaughn says the charisma Lil Skies exhibited during a Baltimore show helped convince him to sign the rapper. "I'm trying to get a week or two before this tour to just chill, get right, be 100%," Lil Skies says. So he headed back to Waynesboro. He adds, "I just be needing that peace of mind."