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Made it in America: The story behind Kanye West and Jay-Z’s unique relationship

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As fans pray for a reunion between two of the world’s greatest hip-hop stars, Sam Moore delves into a timeline of friendship, fallouts and feuds

My little brother is Kanye [West],” Jay-Z told David Letterman in 2018. Two years ago, he and his one-time protégé had gone through a very public falling out over his decision to skip West’s marriage to Kim Kardashian.

By this point, the duo had known each other for almost two decades. They first met in 2000, after West produced a track for Beanie Sigel, a signee to Jay-Z’s Roc-A-Fella Records. Label boss Damon Dash was impressed with the young Chicagoan’s flair for beat-making. He pencilled him in for Jay’s next project.

These days, it’s hard to imagine Kanye West being nervous about anything. He’s one of the most outlandish stars of his time, brash and overconfident to a fault. Certainly not someone you could accuse of lacking in self-belief. Remember, this is the man who once said his greatest pain was that he would never be able to see himself perform live. The one who has compared himself over the years to Steve Jobs, Michael Jordan, Andy Warhol, Walt Disney, Pablo Picasso and Socrates. But coming face-to-face with Jay-Z in the studio, where they created the beat for “This is the Life”, the 23-year-old was apparently so intimidated that he struggled to say “hello” to the man who would soon become his mentor and label boss. Their early collaboration marked the beginnings of a bond that would not only spawn the opulent collaborative album Watch the Throne, but also “Monster”, “Run This Town”, and many other tracks that have helped shape the last 20 years in hip-hop.

Their early days were marked by all-night studio sessions, where they would play beats and lay down rhymes until exhaustion kicked in. One of their very first big successes came when Jay started to assemble his influential album The Blueprint, which celebrates its 20th anniversary this year. The first beat West played was “Heart of the City (Ain’t No Love)” and the second was “Never Change”, two affecting standouts from a classic album. West recalled the session years later, saying Jay-Z simply took off his baseball cap and said: “Yo, put them joints on CD.”

Along with being widely regarded as the architect of The Blueprint’s sound, West was now quickly developing a reputation as one of the best young producers in the business, thanks to his work with other artists including Foxy Brown, Lil Kim, and Scarface. But he wanted more. A lot more. He wanted to be a rapper.

In the early Noughties, the hip-hop landscape was dominated by hardcore gangster rappers such as Jay-Z, DMX, Eminem, Ja Rule and The LOX: men who spat hard and aggressively about the streets, crime, poverty, and violence. Suffice to say West – the middle-class son of a photojournalist and an English professor, who used to work in Gap and dreamt of being a video-game designer – did not fit in. 

Jay and Damon Dash balked at the idea of West joining the competition. “We all grew up street guys who had to do whatever we had to do to get by. Then there’s Kanye, who to my knowledge has never hustled a day in his life.” Jay-Z said in 2005. Yet West was so determined he was ready to defect; he began courting other labels, including Capitol, who came close to signing him in 2002. “Kanye was never down on himself,” Capitol A&R Joe “3H” Weinberger told MTV in 2009. “He’d be ready to rap on the spot, ready to tell his story on the spot, ready to make a record on the spot. He was probably the hungriest dude I ever saw.”

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West had all-but signed to Capitol when the label’s president was persuaded that his records would never sell, and the deal fell through. By now, Dash had seen just how much West wanted this, and finally signed him to Roc-A-Fella as a rapper. “People were on me like, ‘What you gonna do after this?’ I personally signed Kanye, and I wanna take credit for that because I feel good that I believed in him and I saw his vision,” he told MTV. “What I didn’t see was how big his vision was and how he was going to attack it himself. He’s like me and Jay put into one. He’s a businessman, he’s an artist, he’s a producer.”

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From A version of this story originally appeared in the Aug. 28, 2021, issue of Billboard.

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