Jermaine Cole left Fayetteville, North Carolina in 2003 to attend college in New York City. He’d go on to graduate magna cum laude, but the aspiring rapper and producer had bigger dreams—ones that compelled him to stalk JAY-Z’s Roc the Mic Studio, his demo CD in hand. It wasn’t J. Cole’s loitering habit that would make him the first artist signed to Hov's brand-new Roc Nation imprint in 2009, though; it was years spent scribbling in notebooks, studying the sampling techniques of Just Blaze and 9th Wonder, and releasing a steady stream of underground mixtapes. “Lights Please,” rich with hip-hop-as-woman symbolism (à la Common’s “I Used to Love H.E.R.”) and a beat that could’ve come from pre-College Dropout Kanye West, was the track that particularly caught JAY-Z's ear. No flash, no gimmicks, just straight-up great rapping.
Though he’d released a couple of acclaimed mixtapes via Roc Nation in the years leading up to his official studio debut, it was 2011’s Cole World: The Sideline Story that positioned the unassuming rapper among a new hip-hop generation’s upper echelons. The handful of radio smashes—including the massive Kanye sample flip of “Work Out” and the steamy Drake collaboration “In the Morning”—were proof Cole had bona fide star power. Mostly, though, Sideline Story felt like backpack rap gently retooled for the big leagues, with candid storytelling (including, on “Lost Ones,” a heavy back-and-forth between a couple deciding whether to keep an unborn child) over largely self-produced beats. Occasionally, Cole sounds a bit awed that the whole thing worked out, which couldn’t be more of an understatement: Sideline Story was one of the biggest hip-hop debuts of the 2010s, setting the foundation for a generational talent in his own lane.