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The Story of Lil Wayne and Jay-Z, the Best Rappers Alive

Tracing the complicated, brilliant history of the two Mr. Carters in celebration of '4:44.'
Lil Wayne and Jay-Z perform together in 2007 / Screenshot via YouTube

Day 282: "Dough Is What I Got" – Lil WeezyAna Vol. 1, 2006 / "Hello Brooklyn 2.0" feat. Lil Wayne – Jay-Z, American Gangster, 2007

Rap is full of weirdos now, and you have Lil Wayne to thank for it. That side of his legacy—the part where he's zoned out crooning about drugs—is secure, with Lil Uzi Vert hoverboarding the baton into the sunset. But one thing that is less celebrated though no less important about Lil Wayne is his dedication to craftsmanship, which becomes clear when you write about him every day for a year. That hip-hop head part of Wayne hasn't necessarily found its obvious descendants. But his work ethic has been relentless since he was a pre-teen. So is it any surprise that Wayne's favorite rapper has always been rap's most precise, assured MC, Jay-Z?


I've been thinking about Wayne and Jay's relationship in light of Jay's excellent new album, 4:44, which, among many other things, is a tribute to the idea of rap as a craft. Whether it's in the elegant economy of No I.D.'s beats or Jay's casual ease handling the English language or more specifically in the moments where Jay pokes fun at the disposability and short-sightedness of contemporary buzz rap, aping the cadence of 19-year-olds yelling "skrrt," 4:44 prizes a version of rap as self-evidently being about the pursuit of excellence. This is a rarer vision these days, in a world where careers are made on viral singles, but it used to be an assumption baked into what it meant to be a rapper. Wayne didn't claim that he was the best rapper alive because he was trying to stoke a social media narrative to help market his music (not that he didn't see the marketing value); he said it because he genuinely believed it, and he had the meticulous output to back the claim up. He always wanted to be like Jay (who didn't?) because, like Jay, he always knew he was the most talented person in the room. Why not flex your muscles a bit?

In the early days, Wayne's relationship with Jay was open admiration. When he freestyled over Nas's "Ether," he was insistent he was cool with Jay-Z, and he seemed to back it up by rapping over Jay's beats over the years. He even made a mixtape, The Prefix, that basically functioned as a Jay tribute. When he claimed, on "Bring It Back," that he was the "best rapper alive since the best rapper retired," it was a bold claim but it was also a respectful one because, after all, Jay was officially out of the game. Jay was so impressed that he tried to sign Wayne to Roc-a-Fella after the release of Tha Carter, and he did successfully recruit Wayne for the Destiny's Child "Soldier" remix that same year. Things got more complicated, however, when Jay started wading back into the game, particularly given that his return, Kingdom Come, was the weakest he'd ever sounded, and it came at the height of Lil Wayne's momentum-building run.


Jay-Z's comeback single, "Show Me What You Got," was, frankly, lame. So when Lil Wayne came along and torched it, like he was doing with every beat that year, it prompted obvious comparisons between the Carters. Furthermore, Wayne threw a gauntlet of sorts, laying out a "public service announcement" that he was the best rapper alive. "I must be LeBron James if he's Jordan," he raps. "No, I won rings with my performance / I'm more Kobe Bryant of an artist." (It's here, too, where he lays out the famous mantra "we are not the same I am a Martian," which would inspire a whole wave of his persona.) Naturally, people read this as a Jay-Z diss, and it soon became clear that there was tension between the two. Obviously there couldn't be two best rappers now that Jay was back, and obviously Wayne was out-rapping his competitor. But his competitor was Jay-Z. It was indeed a bit like Lebron versus Jordan: Sure, Lebron would win one-on-one these days, but who the fuck is anyone to say he was the better player?

This cold war continued in various starts and stops from around 2006 through at least 2009. On one hand, the writing was on the wall, and Jay wisely saw the importance of embracing Wayne. He brought the young Carter onto his 2007 album American Gangster, mysteriously choosing Wayne for "Hello Brooklyn 2.0" out of all the tracks, when he could have gotten literally anyone from Brooklyn instead. And in 2008, on Tha Carter III, Jay named Wayne his "heir." Still, the two didn't exactly stick to each other.


Not long after "Mr. Carter" was released, Jay was once again intimating that he and Wayne would never be in the same league exactly, recording an "A Milli" freestyle called "A Billi." For those keeping track, though, Wayne had lapped Jay on the one metric Jay has always been able to hold over everyone else, commercial success: Tha Carter III went platinum in its first week, and it netted Wayne a number one single before Jay had one (Jay would only reach that height later with "Empire State of Mind." Later that fall, Jay-Z released "D.O.A. (Death of Auto-Tune)," which naturally scanned as more shots against Wayne, who had emerged as the most enthusiastic proponent of the technology. Wayne fired back in a way—and to be clear, this was a cold war more than anything—by freestyling over "D.O.A." in Auto-Tune. Presumably eventually everyone got kind of bored with the whole thing and went back to being two separate rich dudes, since there wasn't much talk either way in later years. Most recently, though, Wayne has been shouting out the Roc and intimating he's part of Roc Nation, suggesting that after all these years he might have finally ended up on the same team as his idol/rival.

None of this history particularly matters in the scheme of art, other than the fact that Wayne is one of the few rappers who doesn't feel the brunt of Jay's wrath on 4:44. But it does provide a lens through which to view the appeal of each as Jay reasserts his claims to rap dominance with his new album. They are craftsmen, aficionados of rap for the sake of rap, guys who above all want to make the coolest rap music they can (we can safely say this about Jay again, finally). And in that light, too, it's clearer in hindsight that the beef we all saw brewing over "Show Me What You Got" was never as serious as it might have seemed to idle speculators. Of course Wayne was being competitive. Jay would have been disappointed in anything less.


There's a clip of Jay bringing Wayne out to perform in New York around 2007, after the release of American Gangster, when "Duffle Bag Boy" was Wayne's de facto hit. They do "Hello Brooklyn 2.0" with Wayne wearing a Biggie shirt, and when Wayne hits the line about his girl throwing up the Roc the crowd goes nuts. Jay is flawless, obviously, but Wayne is equally sharp, at home performing on that stage with a live band in a way that, if we're being frank, would press almost every current rapper under the age of 25 to the absolute limits of their talent. He owns the stage. You see two stars, totally comfortable. At the end, Wayne shouts out Jay and himself, respectively: "The best rapper alive. And the next rapper in line."

Who is trying to be next in that lineage? It's hard to say. From where I'm sitting, nobody is competing in the same way. Jay knows that, which is part of why 4:44 is so good. All I want now is to see Wayne, the only guy who can give Jay a run for his money, rise to the occasion.

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