Osamason has signed with Wasserman for global representation, because once your third album charts on the Billboard 200 and your festival schedule starts resembling a boarding pass, it’s time to get the touring infrastructure to match.
The South Carolina rapper has quietly built one of the most calculated trajectories out of the underground in recent memory. His breakout singles “Cts-V” and “Troops” started moving numbers online in early 2023, making noise on TikTok, Spotify, and in the group chats that still matter. Since then, he’s dropped three full-lengths in 18 months: Osama Season (July 2023), Flex Musix (December 2023), and Jump Out (January 2025), the last of which became his first Billboard-charting project.
He’s been busy offline, too. Osamason performed at Rolling Loud Miami in 2024, Rolling Loud California earlier this year, and capped his international Wish You Were Here Tour with a finale set at Rolling Loud Thailand—not bad for an artist still straddling the “breakout” label. He’s currently touring across Europe and the UK, where the crowds have caught up to the streaming data.
Speaking of: over 1 million monthly listeners on Spotify, with top markets in Chicago, L.A., NYC, Atlanta, and Dallas—a footprint that says local roots, national base, and international spillover.
Signing with Wasserman doesn’t mark a new beginning. It’s an escalation. The brand is already defined. Now it’s about monetizing the velocity.