Drebb arrived on the music scene in 2016 with his breakthrough mixtape Unknown, with vibes like Eminem and Mac Miller, he followed up with his debut album Schizodramatic in 2017. After starting his indie record label Bayside Records, Drebb became producing for a number of underground artists before releasing The Purple Album in 2019, an album that defined the style that is Drebb. He continued to release music with Bayside Records releasing 4 more rap albums and 2 pop punk albums. He started 2024 releasing a collaboration EP, Michigan Tea Party with Red Larsen to promote his upcoming album Infamous IV.