Penny Glideaway’s story starts in Prince George’s County, Maryland, where he was born before being raised between Nashville, PG County, and Washington, D.C. His environment was always changing, and that carried into his early life—he moved through different schools nearly every year until high school. Despite the constant shifts, he built his identity outside, spending his days and nights skateboarding and playing basketball.
A major part of his upbringing came from the places he spent time in. A local skatepark became his second home, shaping both his lifestyle and creative perspective before it eventually closed. He also spent time at movie theaters, building a deep appreciation for film, and at Six Flags in Maryland, which was a regular destination growing up.
Music became part of his life early. Around the age of 14 or 15, he began experimenting, but it wasn’t until 18 that he started taking it seriously. His inspiration came from a strong foundation of Southern and Midwest hip-hop. Artists like Master P and the No Limit catalog, 8Ball & MJG, Three 6 Mafia, UGK, OutKast, and Do or Die all played a role in shaping his direction. That influence is still present in his sound today.
Penny Glideaway describes his music as rooted in a ‘90s and 2000s lifestyle, driven by samples and a clear sense of nostalgia. His sound reflects the eras that raised him while still feeling current. Recording across PG County, Washington, D.C., and New York City, he continues to pull from each place he’s lived, adding layers to his music and perspective.
His latest release, Tales From Glide Vol. 2, continues his mixtape series and builds on the foundation he’s been developing. With Vol. 3 already in progress, he’s focused on consistency, with more visuals and content on the way.
He also credits those around him as part of his journey. Big Tim the Glider, a close collaborator, appears throughout Tales From the Glide Volumes 1 and 2, with his own project on the horizon. He also acknowledges Frado 180 for his work as a producer and engineer, along with Add’m Fears, a fellow artist and engineer contributing to the movement.
