J. Cole w/ Trippie Redd @ Summerfest

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J. Cole is one of the quintessential modern rap success stories. After making a name for himself on the mixtape circuit, the New York upstart signed to Jay-Z’s Roc Nation label, which released his 2011 debut album, Cole Wold: The Sideline Story, to tremendous commercial success. But rather than leaning into his pop instincts, Cole backed away from them on subsequent albums, which cut back on the guest features expected from big-budget rap albums to create a more introspective vibe. His fifth and latest album KOD is a heady exploration of addiction and depression. Like the four albums before it, it debuted at number one on the Billboard charts.