Meek Mill’s the kind of rapper who treats life like a battle even when he’s winning—or, as he spun it on the intro to 2012’s u003ciu003eDreams and Nightmaresu003c/iu003e, “I’m the type to count a million cash then grind like I’m broke.” It’s not that his themes—struggle, triumph, repeat—are new, but that he manages to make them personal, retaining the urgency of a street artist even while working the mainstream. Raised in North Philadelphia, Mill (born Robert Rihmeek Williams in 1987) got his start with local group The Bloodhoundz, honing his skills in the city's vicious battle scene and turning out a string of solo mixtapes that eventually caught the interest of T.I.’s label, Grand Hustle. Sidelined by an arrest for gun and drug possession, and a seven-month prison sentence, Mill bounced back by signing to Rick Ross’ Maybach Music Group in 2011 and dropping a couple of high-profile collaborations with his new label boss (“Ima Boss,” “Tupac Back”). Mill continued to release music throughout the 2010s, interrupted by stints in jail and house arrest, often for violating parole stemming from his initial 2007 arrest—a case that drew widespread interest from artists and activists, including an op-ed by JAY-Z in u003ciu003eThe New York Timesu003c/iu003e. In 2018, it was discovered that Mill’s arresting officer might have mishandled the case, freeing Mill from jail and, potentially, bringing to a close a decade-long ordeal. Through it all, Mill has established himself as a kind of throwback—a passionate ambassador of classic rap who pitched street stories with a feverish sense of drama: You knew he meant it not just because he said it, but because he yelled it.