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Jay-Z and Lil Wayne, photographed during their “Swagga Like Us” performance at the 51st Annual Grammy Awards at the Staples Center in Los Angeles on February 8, 2009. That evening Hov had been nominated six times and won the gramophone for “Best Rap Performance by a Duo or a Group” for “Swagga Like Us” alongside Wayne, T.I. and Kanye West. Weezy also performed twice during the broadcast. He had received the most nominations with eight, eventually taking home four trophies. 

While there is of course a history of “sporting” beef in their relationship, the foundation of said relationship has always been one of mutual respect and admiration for each other’s craft.

In February 2004 Wayne dropped his mixtape The Prefix, which featured him rapping over eight beats from The Black Album and “Where I’m From.” Later that year on his fourth studio album Tha Carter, Wayne borrowed Hov’s “best rapper alive” title on “Bring It Back,” respectfully rhyming: “I’m the best rapper alive since the best rapper retired.” Later that year, on suggestion from Jigga himself, Destiny’s Child featured the NOLA rapper on their hit single “Soldier” and helped push him into pop stardom.

Predicting the career trajectory of the younger Carter and wanting to support his ascent to the top of the rap game, in December 2004 Jay-Z, in his role as the Def Jam Recordings President and CEO, tried to recruit Wayne to his Roc-A-Fella Records subsidiary during his free agency. In a daytime meeting at The 40/40 Club attended by Denzel Washington and Derek Jeter, Jay tried to explain to Wayne the freedoms and support he could offer him at Def Jam, telling him “Dude, whenever you get out of your situation, I’m here. Whatever you need, I’m always here.” President Carter reportedly offered the younger Carter $175,000 cash on the spot, with more to follow when they finished the meeting in Jay’s office. A few days later Wayne received a call from the higher ups at Universal Music Group, in which the words “millions” and “your own label” were intentionally dropped multiple times to convince him to stay. As we know, Wayne would re-sign with Cash Money in February 2005 and launched Young Money Entertainment later that year. 

In a 2013 interview with Power 105.1′s “The Breakfast Club” JAY Z would, for the first time ever, reveal the truth of why his plan to sign and support Lil Wayne didn’t come to fruition. “The truth is, I had a meeting with Wayne. I had a relationship with Baby—I used to go to New Orleans and I’d hang out with him. He had me in the purple [Plymouth ‘Prowler’] going down the street, no top, people trying to jump in the car. So I felt it was only right to call him,” Hov explained, noting how he and Birdman were once friends and he wanted to show respect. “So I called him out of respect, like, ‘Oh, I was talking to Wayne [about a deal], just letting you know.’ After that Def Jam received a letter at our office for ‘Torturous Interference.’ I was like ‘Oh, wow!’ And it just all went from there. [But] I would rather lose that situation and do the right thing than do the opposite. I could’ve signed him and then told him after, but I did the right thing. I’m cool with that decision.” 

However Jay wouldn’t hold Wayne’s UMG decision—or his 2006 run of subliminal and direct shots on wax and interviews—against him, recruiting Tunichi for their first ever collaboration on “Hello Brooklyn 2.0” in 2007 and later returning the feature favor on “Mr. Carter” in 2008. “Swagga Like Us” would mark the third time they worked together. In a July 2008 interview with People magazine Weezy F. Baby told the publication that Jay’s 1997 cut “Lucky Me” is his “favorite song of all time. Period. I actually have ‘Lucky Me’ tattooed on my neck. And I have a verse of that song tattooed on my leg.“

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