OsamaSon broke through in 2023 with the self-released mixtape Osama Season, which quickly found a wide audience through social media and fan-based platforms. The project marked the start of a new wave of rap artists operating outside the traditional music industry and instead building their careers through social media, constant releases and direct contact with fans.

Since his debut release, OsamaSon has been productive with several notable projects, including Flex Musix and his debut album Jump Out, which was released in January 2025. The album reached #151 on the Billboard 200 and was recognized by several leading media outlets, including Pitchfork, who awarded it a “Best New Music” recommendation.

OsamaSon has managed to maintain a consistent stream of releases while moving from the underground to bigger stages.

During 2024 and 2025, he has played sold-out shows in the US and Europe and performed at several festivals.