The Oakland-born Lillard started rhyming while in middle school, and wrote his first verse a few years later for his high school basketball team. Around that time, he was featured on J-Black's "Get It How You Live." After he established his pro career in the NBA -- he won the league's 2013 Rookie of the Year honor and was an all-star for the following two seasons -- he continued to make progress with music. He issued some singles in 2014 and 2015 and released his debut full-length, The Letter O, in 2016. Issued a few days before he began his fifth season with the Portland Trail Blazers, the album featured fellow Bay Area dwellers Danny from Sobrante and Brookfield Duece, as well as Marsha Ambrosius, Lil Wayne, and Jamie Foxx. It debuted at number 119 on the Billboard 200 (and at number seven on the R&B/hip-hop chart). Confirmed followed the next year with another verse from Wayne, plus additional support from 2 Chainz and BJ the Chicago Kid.
Lillard released his third album, Big D.O.L.L.A., in 2019. The guest list boasted Jeremih, Mozzy, Major Myjah, and Derrick Milano, as well as Lil Wayne. In 2020 he teamed with Snoop Dogg and Derrick Milano for the single "Kobe," a tribute to departed NBA superstar Kobe Bryant. The following year, he issues his fourth album, Different on Levels the Lord Allowed, with guest appearances from Q-Tip, Dreebo, Raphael Saadiq, and many others. ~ Andy Kellman, Rovi