A rapper and actor who secured a recording contract before a driver's license, Diggy Simmons landed a major-label deal with Atlantic on the strength of his debut mixtape, The First Flight (2009). Within two years, he had his first charting single with "Copy, Paste" and considerable media notice via placement in XXL's Freshman Class, which led to the Top 15 debut album Unexpected Arrival. An assortment of singles and acting gigs, including a role on Grown-ish, preceded the release of his follow-up project, the independent Lighten Up (2018).

The son of Joseph Rev Run Simmons from the legendary Run-D.M.C., Daniel Diggy Simmons -- born in the New York City borough of Queens, like his father -- first came to the public's attention in 2005, when he appeared with his family on the reality television show Run's House. Four years later, he staked his claim with The First Flight, a mixtape hosted by DJ SpinKing. Early in 2010, a freestyle he recorded over the instrumental version of Nas' "Made You Look" became a viral hit, and it didn't take long for Atlantic Records to come calling, contract in hand. Then only 15 years old, Simmons signed and celebrated with the release of Airborne, a mixtape that included "Great Expectations," which was featured in a national ad campaign for a major American cell phone service. In 2011, he released the Pop Oak-produced single "Copy, Paste" -- which peaked at number 24 on Billboard's R&B/Hip-Hop Singles chart -- and was featured on Mindless Behavior's Top Ten R&B/hip-hop hit "Mrs. Right." After appearing on Jacob Latimore's "Like 'Em All," charting with the Jeremih collaboration "Do It Like You," and being selected for XXL magazine's annual Freshman Class, Simmons completed his debut album. Unexpected Arrival, on which he worked with the likes of D'Mile, Pop Oak, and Soundz, among other producers, was released in March 2012 and debuted on the Billboard 200 at number 13. A mix of acting roles and occasional singles followed during the next few years. In November 2018, after he appeared in multiple episodes in the first season of Black-ish spin-off Grown-ish, he returned to music with the brief independent set Lighten Up. ~ David Jeffries & Andy Kellman, Rovi