Celebrities Who Successfully Re-Emerged After Serving Jail Time

Inspired by Philadelphia hip-hop legends Will Smith and DJ Jazzy Jeff, Meek Mill began his career as a battle rapper. He collaborated with Rick Ross on “Tupac Back” and “Ima Boss,” and in 2012 released his debut album, “Dreams and Nightmares,” which peaked at No. 2 on Billboard’s Hot Rap Songs chart. Three years later, he topped the chart with his follow-up, “Dreams Worth More Than Money.”

In 2008, Meek was convicted of a drug and firearm charge and sentenced to two years in prison and eight more in probation. In 2018, he was given an additional four years for minor probation violations. After five months in jail, Pennsylvania’s Supreme Court granted him bail.

Meek returned to the studio with a vengeance, releasing the Grammy-nominated “Championships” in 2018. The album’s hit single, “Going Bad,” featuring Drake, spent 37 weeks on Billboard’s Hot 100. In 2023, the rapper made an ambitious resolution to release an album every quarter. Drake, who made a special appearance at Meek’s 2019 Motivation Tour in Los Angeles, praised his friend for having “the best comeback of all time.”