Before Jermaine Lamarr Cole went toe-to-toe with rap greats, he was a 20-year-old college student with nothing more than a dollar and a dream, perched outside of New York City’s Baseline Studio in the rain, hoping to hand his demo to idol JAY-Z. He wouldn’t end up meeting JAY-Z that day, and wouldn’t for nearly five years. But this crucial in-between period—defined by sleepless nights, undying hope and untold hours spent perfecting his skills—would end up fueling Cole’s 2011 major label debut, Cole World: The Sideline Story. It’s an album that doubles as a blueprint for how to successfully break into the game—the kind of record the North Carolina MC could have used when he was younger. As he says himself: “I wish somebody made guidelines/On how to get up off the sidelines.” Sonically, The Sideline Story introduced the mainstream market to Cole’s signature sound: warm, triumphant and nostalgic. It’s a style that had been forged on early mixtapes like Friday Night Lights and The Warm Up, both of which are represented here by a handful of tracks. And while previously unheard deep cuts like “Rise and Shine” give the feeling of watching your favourite sports team’s homecoming, the delicate pianos of “Sideline Story”—which are sprinkled all over the album—invite vulnerability and introspection. That kind of duality can be found throughout The Sideline Story, which is sometimes split between “radio” Cole and “conscious” Cole. The more commercial moments here would introduce already die-hard fans to a more light-hearted side of Cole, on such songs as “Who Dat” and “Can’t Get Enough”. But deep cuts like “Lost Ones” and “Breakdown” examine topics like abortion and abandonment with the utmost care and grace. Still, the rapper’s ongoing battle between right and wrong remains the lyrical centre of the album. You can hear that inner conflict most clearly on “Lights Please”, the track that had found its way to label-head JAY-Z, eventually earning Cole a deal with Jay’s new company, Roc Nation. The Sideline Story, which debuted at the top of the US album charts, would mark a monumental moment for both men: It proved JAY-Z could still nurture and introduce new talent, and demonstrated that Cole’s mixtape infamy could be translated into big-time fame.