In a region often overlooked by the mainstream, Playtime Milly is making sure Upstate New York has a seat at the table. Born and raised in the heart of Upstate, Milly’s music carries the grit of his surroundings, but also a kind of hope you only find in people used to making something out of nothing.
Milly’s introduction to music wasn’t a product of chasing trends or trying to fit in. It was Travis McCoy—frontman of Gym Class Heroes and a fellow Upstate native—who lit the first spark. “Seeing someone from where I’m from make it big, it made me believe it was possible,” Milly says. That belief turned into late nights writing, recording, and shaping a sound that feels like no one else’s.
What sets Playtime Milly apart isn’t just the beats or the bars—it’s the raw authenticity in everything he does. He’s not interested in playing a part, and it shows. “I peeped all the red flags in them, gave them the shirt off my back now they just keep stabbing it,” he spits—a line that hits hard because you know it’s lived experience, not just clever wordplay.
In an era where everybody’s chasing numbers and viral moments, Milly stands out for something harder to fake: believability. He’s not afraid to let people in on the scars, the setbacks, and the loyalty that sometimes gets you hurt. There’s a vulnerability in his music that’s rare, but it’s always balanced by the confidence of someone who knows exactly who he is.
And if you haven’t heard what he’s been cooking lately, now’s the time. Playtime Milly just dropped four new singles: “762 Freestyle,” “Easy,” “Where I’m Goin,” and “Do a Lot.” Each track is a different side of the same story—gritty, melodic, and full of the kind of lines that stick with you long after the song ends.
Upstate NY might not have the industry’s brightest spotlight, but with artists like Playtime Milly, it doesn’t need one. The music speaks for itself, and the story’s just getting started.