Damian Lillard, known as Dame D.O.L.L.A., has successfully balanced a career in the NBA with a thriving music career, releasing independent projects like The Letter O and Big D.O.L.L.A., gaining recognition from notable artists such as Lil Wayne and 2 Chainz. Dame's musical journey began in middle school with freestyle battles, leading to his acclaimed debut freestyle on Sway in the Morning in 2015, which garnered over 10 million views on YouTube. His debut full-length album, The Letter O, debuted at number 119 on the Billboard 200, showcasing collaborations with Lil Wayne and Raphael Saadiq.

His second project, CONFIRMED, featured production from Scott Storch and collaborations with BJ The Chicago Kid, Lil Wayne, and 2 Chainz. Dame's third album, Big D.O.L.L.A., released in August 2019, includes features from Jeremih and Lil Wayne, with production from 808 Mafia's Fuse, OG Parker, and Nonstop Da Hitman, solidifying his presence in both the music and basketball worlds.