Originally known as D-Bo, he was a member of Dirt Gang, associated with Waka Flocka Flame's Brick Squad Monopoly crew, and frequently collaborated with Slim Dunkin. Following Dunkin's death in 2011, Lenard stopped rapping for a while. He briefly went by the name D Dash before eventually deciding to settle on Derez De'Shon. He caught the attention of Cash Money CEO Birdman, which led to an appearance on Rich Gang's 2016 single "Pull Up." The Pain mixtape, hosted by DJ Drama and featuring appearances from Birdman and Jeremih, was released in 2017. Pain would be the beginning of Lenard's rise to fame, with the songs "Ambition" and "Hardaway" both gaining a lot of local attention, and "Hardaway" breaking through on a national level. The track's video was viewed more than a hundred million times, and a remix featuring Yo Gotti and 2 Chainz showed up soon. This newfound acclaim led to demand for an expanded deluxe edition of Pain, which arrived in 2018, and before the year was out, he returned with the Pain 2 mixtape. The project spoke to Derez De'Shon's growing fame, including guest spots from big-name rappers Lil Durk, Mozzy, Lil Baby, and others. Pain 3 arrived in August 2020 and featured appearances by A Boogie wit da Hoodie, Boosie Badazz, and Ralo. ~ Paul Simpson, Rovi