There may not be two rappers whose relationship better represents Hip-Hop’s complicated obsession with competition than JAŸ-Z and Lil Wayne. For nearly two decades, the two Carters have bounced between admiration, collaboration, and the occasional subliminal — or not so subliminal — shot, all while making it clear that there has always been a tremendous amount of respect between them.
At the center of much of that tension was one of rap’s biggest questions: Who is the best rapper alive? By the early 2000s, JAŸ-Z had already established himself as one of Hip-Hop’s standard-bearers, and his 2003 retirement briefly made the title feel available for someone else to claim. Wayne was more than willing to volunteer.
On 2005’s Tha Carter II, Wayne famously declared himself the “best rapper alive,” after previously qualifying the claim by saying he held the title only because “the best rapper retired.” But when JAŸ-Z returned to recording, there were suddenly two MCs who could reasonably view themselves as sitting at the top of rap, helping create a competitive dynamic that followed them for years.
What makes their history so interesting, though, is that it never stayed in one place for very long. JAŸ-Z once explored signing Wayne; they traded bars that fans interpreted as shots, appeared on each other’s albums, and eventually developed the type of friendship in which Hov reportedly helped Wayne during one of the most difficult financial periods of his life. Here are the biggest moments in the complicated history between Lil Wayne and JAŸ-Z.
2004-2005: JAŸ-Z Tries To Bring Lil Wayne To Roc-A-Fella
As Wayne began transforming from a former teenage Cash Money star into one of rap’s most formidable MCs, JAŸ-Z apparently saw the potential early. Hov explored bringing Wayne to Roc-A-Fella around 2004-05, but Cash Money remained in the picture and the deal never materialized. Wayne later recalled being offered roughly $175,000 during a meeting with Jay, an amount he said was nowhere near what he expected.
2005-2007: Wayne Comes For The “Best Rapper Alive” Crown
Tha Carter II marked the point when Wayne stopped treating JAŸ-Z’s retirement as a qualifier and simply began calling himself the best rapper alive. During an increasingly dominant mixtape run, Wayne’s confidence only grew, and by 2007 comments about being better than Jay had created enough attention that Wayne publicly apologized for how one particular interview had been presented while still maintaining his belief in his own ability.
2007: JAŸ-Z Appears To Warn Wayne On “Watch What You Say To Me”
JAŸ-Z’s verse on T.I.’s “Watch What You Say To Me” was widely interpreted as a response to Wayne’s increasingly bold comments. Jay referenced someone “baiting” him and reminded the unnamed target of his influence on their music, which immediately fueled speculation that Wayne was the intended recipient. Neither rapper turned the moment into an outright declaration of war.
November 2007: “Hello Brooklyn 2.0” Shows There’s Still Respect
Just when it appeared the two might be moving toward a real battle, Wayne appeared on “Hello Brooklyn 2.0” from JAŸ-Z’s American Gangster. During a performance with Jay that same month, Wayne even pointed toward Hov and called him the “best rapper alive” before referring to himself as the “next rapper alive,” publicly cooling much of the feud talk.
2008: JAŸ-Z Passes The Torch On “Mr. Carter”
The respect became even clearer when JAŸ-Z appeared on “Mr. Carter” from Wayne’s blockbuster Tha Carter III. Jay referred to Wayne as his “heir” while encouraging the younger Carter to go further, turning the record into one of Hip-Hop’s most memorable symbolic torch-passing moments. They would also join Kanye West and T.I. on “Swagga Like Us” later that year.
2011: “Baby Money” Reignited The Tension
Things got considerably less friendly during the Watch The Throne era. On Kanye West and JAŸ-Z’s “H.A.M.,” Jay rapped about someone having “baby money,” a line widely interpreted as a swipe at Cash Money co-founder Birdman after Birdman publicly compared Wayne’s money and status with JAŸ-Z’s.
August 2011: Wayne Fires Back On “It’s Good”
Wayne removed much of the ambiguity on Tha Carter IV track “It’s Good.” Referencing “Baby money,” Wayne followed it with a threat involving JAŸ-Z’s wife, Beyoncé, making it one of the clearest shots either rapper had taken during their entire back-and-forth. Wayne later said music was about perception and indicated that he was not worried about repercussions from the verse.
2013: JAŸ-Z Appears To Answer On “La Familia”
Two years later, JAŸ-Z appeared to revisit Wayne’s “It’s Good” line on Magna Carta Holy Grail. On “La Familia,” Jay referenced someone wanting to kidnap his wife and warned that person they would have to hide their entire family, seemingly providing a delayed response to Wayne’s verse.
2015: Wayne Teams Up With JAŸ-Z During His Cash Money Battle
By the middle of the decade, their relationship had taken another dramatic turn. During Wayne’s bitter dispute with Birdman and Cash Money over Tha Carter V and money he claimed he was owed, Wayne announced a deal with his “idol,” JAŸ-Z, that ultimately involved Tidal, where he released Free Weezy Album. Cash Money later sued Tidal over the release.
2018: Wayne Reveals JAŸ-Z Helped Him Financially
Perhaps the clearest indication that the old competition had evolved into genuine friendship came when Wayne told fans that JAŸ-Z helped him while he was struggling financially. During his I Ain’t Shit Without You Tour, Wayne revealed that Hov helped him deal with a multimillion-dollar tax situation, something he said Jay never wanted him to make public.
2023: The “Best Rapper” Debate Comes Full Circle
Almost two decades after Wayne first started chasing JAŸ-Z’s crown, the debate was still alive. Wayne argued that he should rank above Hov when discussing an all-time rapper list, but that same year he also included JAŸ-Z among his personal five greatest rappers and continued speaking about Jay as one of his biggest influences. Juvenile even revealed that Wayne routinely tells him JAŸ-Z is the GOAT.
That contradiction may actually sum up their relationship better than anything else. Wayne has spent much of his career believing he can out-rap anybody — including one of his heroes — while never hiding how much JAŸ-Z influenced him. What once looked like a fight over Hip-Hop’s throne eventually became something closer to mutual recognition between two rappers who both built legitimate cases for sitting on it.
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