A Timeline of Lil Wayne and Jay-Z’s Relationship

We wouldn’t call Jay-Z and Lil Wayne frenemies, but they’ve definitely had a journey, one fans were called to remember when Kendrick Lamar was announced as the headlining performer for Super Bowl LIX last weekend. For the last five years, Jay-Z’s Roc Nation has helped the NFL choose the halftime performers for the biggest performance of the year. New Orleans is the host city for this year’s Super Bowl, so when Kendrick was chosen fans quickly came to the defense of Wayne, the greatest rapper to come out of the state of Louisiana.

After the news was announced, you started hearing murmurs from fans that Wayne, who had been actively campaigning to headline the performance, should have been the one chosen. The murmurs became screams by Monday, when Lil Wayne’s Young Money compatriot Nicki Minaj got involved.

In a flurry of tweets she unloaded, Nicki seemed to suggest that Jay-Z was punishing Weezy by not letting him perform at the Super Bowl. While she didn’t get specific, she implied that Jay has some unresolved issues with Drake, and that choosing Kendrick as the Super Bowl headliner over Weezy was a way of punishing the 6ix God. (It’s a theory supported by the punditry class also, with Cam’ron, Mase, and Joe Budden sending out their own theories.)

Hov has yet to make an official comment about Wayne or Drake. (He did, however, have very nice things to say about Kendrick.). But since the convo is at our doorstep again, let’s re-examine the storied connection between Weezy F and his admitted idol, Jay-Z. Their relationship goes back nearly 20 years. It’s not clear when it started, but the first interaction between the two came when Jay randomly called him out of the blue. Wayne said the conversation was brief, he told ex-ESPN anchor Cari Champion, “All he really said is ‘Sup, lil homie. I see you. Just wanted to let you know, I see you.’” From there the two would have a relationship that would take a bunch of twists and turns.

Here is a timeline of their long history.

2002: Lil Wayne shouts out Jay-Z on “Ether” freestyle

True Weezy fans know The Squad Up years was when Lil Wayne went through the scars needed to be the best rapper in the world. On those tapes, you can hear him develop from a child rapper to an adult, embracing more East Coast driven rhyme schemes and punchlines.

The Jay-Z influence is in almost every verse. So it wasn’t surprising when Wayne freestyled over Nas' "Ether," saying "I fucks wit' the homie, man, sorry” during the “fuck Jay-Z" portion of the song.

February 2004: Lil Wayne releases ‘The Prefix,’ a mixtape where he raps over multiple Jay-Z beats

Twenty years ago, Weezy used his mixtape, The Prefix, to show his admiration for Jay-Z in subtle ways. He released The Prefix, a mixtape where he raps over numerous classic Jay-Z cuts, including “Where I’m From,” “Encore,” and “Dirt off Your Shoulder.”

The highlight of the tape is when he wrecks “Moment of Clarity,” spitting lines like, “Change mind sporadically, same time compatibly/Wayne Carter, graduate, bang bang academy” while distancing himself from his old Squad Up click.

The Prefix really is the start of Wayne’s legendary run: he would release Tha Carter just a couple of months later. The rest, as we like to say, is history.

June 2004: Weezy nods to HOV on “Bring It Back”

While Tha Carter II and The Carter III are his most heralded albums, the first Carter was the true beginning of Weezy’s Best Rapper Alive candidacy; it was clear he was an emerging legend, with Wayne’s sly wordplay and increasingly refined mic presence improving tremendously.

He himself appeared to be aware of the moment when he nodded to Jay, who was in the midst of a brief fake retirement. Skittering over "Bring it Back," Weezy declared himself the man on the rap throne: “The best rapper alive/Since the best rapper retired.” He doesn’t say Jay-Z’s name, but it’s clear who he was talking about. Jay famously declared himself the best rapper alive during multiple points of his would-be final album, The Black Album, the year prior. A year later, Wayne would double down on his proclamation, releasing "Best Rapper Alive" on Tha Carter II.

May 2005: Lil Wayne reveals that he considered signing With Jay-Z

Yes, Weezy did, indeed, consider signing to Roc-A-Fella Records years ago. He addressed the topic on “Wayne Explains His Deal,” a skit featured on his legendary May 2005 mixtape, Dedication. According to Wayne, Jay made it known he was available to help with whatever—even if Jay only offered him $175,000 to sign to the Roc, something he revealed in a 2016 interview. He ultimately accepted a deal with Universal after they offered him “millions” of dollars. Jay himself later confirmed he tried to sign Weezy in a 2013 interview with The Breakfast Club.

November 2006: Lil Wayne Nods to Jay-Z Again With “Dough is What I Got” Freestyle

By fall 2006, Jay-Z’s self-imposed “retirement” had come to an end with the release of “Show Me What You Got,” a competent single that announced his then-forthcoming album, Kingdom Come.

So, what better way for Weezy to affirm his dominance than jack Jay’s beat for a far superior remix? It comes with the quippy Hova flip, too: “When it comes down to this recording/I must be LeBron James if he's Jordan/No—I won rings with my performance/I'm more Kobe Bryant of an artist/Same coach, same game, been starting/Same Triangle Offense.” It’s not exactly shots fired but, you know...it kinda is.

“Dough is What I Got” is still one of Wayne’s best freestyles. And it definitely got Jay’s attention. In 2020, Wayne appeared on Drink Champs and N.O.R.E shared text messages from Jay, where he talked about the song. “When he rapped on ‘Show Me What You Got,’ I had to take a long walk and look at myself in the mirror,” Jay wrote. “I said, ‘Are you sure you still got this?’”

November 2006: Jay-Z fires shots back at Lil Wayne…maybe?

One of the standouts on Kingdom Come is “Trouble,” a Dr. Dre-produced banger that LeBron James apparently loves. On the third verse Jay takes shots at an unnamed foe, constantly using “lil nigga.”

Here is a sample lyrics:

“Unlike you lil' nigga, I'm a grown ass man/Big shoes to fill nigga, grown ass pants/Probably hustled with your pops, go ask your parents/It's apparent you're staring at a legend who/Put a few lil' niggas in their place before/Trying to eat without saying their grace before/Blasphemous bastard get your faith restored.”

Jay has a history with subs, so don't discount this one.

December 2006: Lil Wayne tells Complex he’s better than Jay-Z

Speaking to Complex for a cover story, Weezy finally, point blank, said he was better than the newly unretired Jay. He apparently didn’t like Hov’s hip-hop savior sentiments: “I’m better than [Jay-Z]. I don’t like what he’s saying about how he had to come back because hip-hop’s dead and we need him. What the fuck do you mean? If anything it’s reborn, so he’s probably having a problem with that. You left on a good note, and all of the artists were saying, ‘Yo, this is Jay’s house. He’s the best.’ Now he comes back and still thinks it’s his house,” Wayne said. “It’s not your house anymore, and I’m better than you.”

April 2007: Weezy apologizes to Jay-Z

Welp, that didn’t last too long. Speaking to XXL for an April 2007 cover story, Weezy walked away from his “Better than Jay-Z” comments, apologizing to HOV in the process.

“I wanna apologize to Jay and his family and friends, because I was asked that question and they put it in there like I was just feeling like, ‘Oh, you know what, nigga? I’m better than Jay!’ They came at me like, “So you say you’re the best. Can you say that you’re better than everybody? Would you say you’re better than Jay?’ I was like, ‘Yeah, nigga, I’m better than everybody!’ But I’d like to throw that apology out there ’cause of whatever trouble I caused, I ain’t want that to happen.”

July 2007: Jay-Z responds to Weezy?

It looks like Weezy’s apology might have fallen on deaf ears. Teaming up with T.I. for his T.I. Vs. T.I.P. cut “Watch What You Say To Me, Jay had some words for a certain artist who had apparently been calling him out: “I hear you baitin' me lately/I been doin' my best just to stay hater-free/Still watch what you say to me/Sooner or later, I take you up on your offer/And put you all in your place like I'm replacing your father/You talkin' to the author, the architect of The Blueprint/My DNA in your music—motherfucker, you stupid?”

Again, the barb doesn’t explicitly name Weezy, but the part about “DNA in your music” and the reference to someone’s father (Birdman?) make this one feel like it’s pointed to Weezy. You be the judge.

November 2007: HOV and Weezy collaborate for the first time

At this point, Weezy was in the middle of one of the greatest guest verse and remix runs of all time. Meanwhile, Jay was brushing off the dust of a mediocre comeback album. In the fall of 2007, he dropped American Gangster, a proverbial return-to-form LP.

With both rappers carrying a lot of momentum, it’s only right they teamed up. And they did for “Hello Brooklyn 2.0.,” a song that sounds a little odd on American Gangster but is still incredible. During a subsequent Hammerstein Ballroom performance of the track later that month, Weezy performed the song with Jay. He then told the crowd that HOV was still the best rapper alive and that Weezy himself was the “next rapper in line.”

June 2008: Jay and Weezy reunite on “Mr. Carter”

Released on Weezy’s seminal album Tha Carter III, “Mr. Carter” is a playful standout that felt a bit more natural than their first track together. It also serves as the moment Jay “passed the torch” to Weezy, whose commercial and critical success made it the only option for the aging MC.

On the track Jay raps: “ I'm so fly I'm on auto/Pilot, while guys just stare at my wardrobe/I see Euros, that's right: plural/I took so much change from this rap game, it's your go.”

June 2008: Jay-Z Hops on Lil Wayne’s “A Milli”

Years before he became a literal billionaire, HOV got into some manifesting with a freestyle over Weezy’s “A Milli,” an extremely, extremely popular track from Tha Carter III. (There were many “A Milii” freestyles during this era.) Here, HOV lets the flexes go in a way that would make Weezy blush. And of course, about 11 years later, he would officially be certified an actual billionaire.

July 2008: Lil Wayne reveals the true extent of his Hov fandom

Speaking with People in July 2008, Weezy showed the world that there are truly levels to rap fandom. He told the publication that he got two Jay-Z’s tattoos on him. Both are paying homage to the In My Lifetime Vol. 1 gem, “Lucky Me.” He got the song title tattooed on his neck and he’s got a verse from the track tatted on his leg. Talk about commitment.

September 2008: HOV and Weezy appear on “Swagga Like Us” Together

“Swagga Like Us” was a track that grouped the world’s four biggest rappers at time on the same damn song. Those artists were T.I., ’Ye (formerly known as Kanye West), Lil Wayne, and Jay-Z. The track was an epic one that only further solidified members of this quartet as the biggest things in all of hip-hop. The song was technically T.I.’s so he got dibs on having the final verse.

The four would famously perform the song with a very pregnant M.I.A. at the 2009 Grammys. The Grammys might not always respect hip-hop, but this one was a no-brainer. The four biggest MCs in the world hit the stage to perform “Swagger Like Us” for a brief show that was basically a microcosm of the late 2000s mainstream rap scene. Sorry about the video quality, but just goes to show you how long ago this was.

October 2008: HOV and Weezy co-headline Power 105.1 concert

Man, these two were really tapped in back then, huh? After appearing on multiple tracks together and hefting praise each other’s way seemingly every few months, the two were chosen to co-headline the Power 105.1 concert 16 years ago. Whether they were sharing the stage or the same song, the connection was clearly pretty damn strong by 2008, preceding sneak disses be damned.

June 2009: Jay shouts out Weezy on haterfest “DOA (Death of Auto-Tune)"

By any account, "DOA (Death of Auto-Tune)" is Jay-Z at his most crotchety. Seriously, telling folks to cut out Auto-Tune felt kind of lame at the time, but now, it’s just down right unacceptable.

Interestingly, though, he made time to show Weezy—a frequent Auto-Tune user—some love on the track, saying that he might send the track to “the mixtape Weezy.” Of course, Weezy would jump on the beat for his No Ceilings mixtape that fall.

October 2009: Birdman says Lil Wayne is richer than Jay-Z

Birdman didn’t take too kindly to MTV naming Jay-Z the hottest MC in the game. Speaking to Tropical TV, Birdman made it clear that he disagreed with the network’s criteria: "I don't think [Jay-Z] is the No. 1 MC in no kind of way. Wayne's the best. He do the most and he make the most money. I don't think no nigga in the business make more money than us. How can you be the best if you don't make the most money? And you don't do the most? Lyrically, come on man, be for real, can't nobody fuck with Wayne...If you number one and you ain't getting no money it don't mean nothing."

November 2009: Jay gives Weezy a shoutout on “A Star Is Born”

For his Blueprint 3 cut “A Star Is Born,” Jay once again gives props to Weezy, rapping, “Wayne’s scorching/I’ll applaud him/If he keeps going/Pass the torch to him.”

Sounds really cool, but question: how many times can he pass the torch? And what’s the status of that?

January 2010: Jay-Z responds to Birdman

Speaking with Hot 97’s Angie Martinez, Jay responded to Birdman’s quips. He didn’t get into the “better lyricist” claims too much, but when it came to the money, well…he just kept it real. "Being lyrical is just a matter of opinion. It's who you like," Hov said. "As far as money, that's a little more factual,” he added before suggesting that Weezy’s bank account probably wasn’t on his level. It’s a playful, respectful response, but things could’ve gone very left, and the somewhat hard-earned peace between Jay and Weezy could have been put in jeopardy.

March 2010: Weezy jumps onstage to perform alongside Jeezy at the Blueprint 3 tour Stop at Madison Square Garden

The 2010s were a turbulent time for Lil Wayne. At the end of 2009 he pleaded guilty to attempted criminal possession of a weapon in New York City, which meant he had to serve a year in jail. He was supposed to start his stint at the top of 2010 but the sentence was delayed.

Weezy used his borrowed time to rap alongside Jay-Z during the Madison Square Garden stop of his Blueprint 3 tour. For good measure, Drake and Nicki Minaj pulled up, too.

June 2010: Jay admits Weezy motivates him

Speaking with Rolling Stone in 2010, Jay admitted that Lil Wayne’s level of rapping gave him an incentive to make an album like The Blueprint 3.

“One of the reasons I wanted to make Blueprint 3 was because of the challenge,” Jay said. “We've seen people like LL [Cool J] have longevity, and we respect the heritage of what he's done, but it's not like, right now, he's competing on the same level as Lil Wayne. So for me to still be able to compete at that level at my age, that's rarefied air. It's never been done.”

June 2010: Weezy gives props to Jay-Z’s “Light Up” verse

Speaking to Mack Maine in a prison phone call, Weezy gave it up to Jay-Z for delivering a stellar verse on “Light Up,” a standout from Drake’s debut album, Thank Me Later. “Ain't nobody talking about what your boy talking about,” Weezy said at the time. “ That nigga is stupid [with his rhymes]! I said, 'Oooh, look at that.'

January 2011: Jay-Z gives Weezy the Subway Treatment on “H.A.M.”

Hov didn’t let being on relatively good terms with Weezy stop him from getting off an apparent Lil Wayne sub. For the record, Jay seemingly alludes to Lil Wayne’s record label, Young Money, while appearing to nod at Birdman’s comment about Wayne being richer. Mind you, Birdman’s comments were over a year old at this point. Jay raps, “Really, half a billi,' nigga, really? You got baby money/Keep it real with niggas, niggas ain't got my lady money.” So…if you hadn’t guessed, this is where the real war started.

March 2011: Lil Wayne responds to Jay in interview

At first, Wayne offered up a surprisingly humble response to Hov’s barb. At this point, Jay was essentially the richest rapper around and, as big as Weezy was, it wasn’t a competition—at least when it came to money.

“I wouldn't make it a competition, because actually, the subject that he's talking about in that line, I can't box with the god. I'd be the first one to tell you that, given my wit, and the type of person that I am, I'd capitalize and I'd play off of it,” Wayne said at the time.

August 2011: Lil Wayne claps back at Jay with “It’s Good”

Naturally, Weezy it was only a matter of time before Weezy responded to Jay wax, and he did so with “It’s Good,” a fiery Jadakiss and Drake-assisted track that sees Weezy get a little reckless, letting the beat drop and everything. Wayne rapped: "Talkin' 'bout baby money, I got your baby money / Kidnap your bitch, Get that ‘how much you love your lady?' money/I know you fake nigga/Press your brakes nigga."

Now, it became a blood sport.

February 2012: Weezy subs Jay in pre-Grammy freestyle

Months after Jay and ’Ye teamed up for their epic Watch the Throne joint album, Wayne used a pre-Grammys freestyle to throw some darts at HOV: “I met a bad red bone, I took the bitch home/ I asked her what she want to watch, she said surely not The Throne,” he rapped. Clearly Hov’s line still bothered Weezy a little more than he wanted to admit.

July 2013: Jay-Z responds to Weezy’s “It’s Good” diss two years later

Interestingly, Jay-Z actually recorded some of Magna Carter: Holy Grail around the time he worked on Watch The Throne with ’Ye. So then, it’s not all that surprising to hear that Jay responded to Weezy’s “It’s Good” verse on the album. For the track “La Familia,” Jay let loose in a verse that sounded a bit dated by the time it was released. On the song he rapped, “Wanna kidnap wifey? Good luck with that bruh/You must gonna hide your whole family, what you think we wearing black for?”

May 2014: Weezy gives D’usse a big shoutout via song title

Leading up to what was supposed to be the release date for Tha Carter V, Lil Wayne dropped a track called “D’usse,” a title that invokes the liquor brand Hov had a stake in at the time. Speaking with MTV News, Wayne explained that he had been sipping on it a lot at the time and that he never had a problem giving it up to Big Jay. So, at this point it seemed like there was no bad blood between the MCs. But would that really be the end of their problems?

June 2015: Weezy links with tidal

Months after complaining about his label situation and announcing a $51 million lawsuit against Cash Money Records, Wayne came to Death Row—err, Tidal, Jay-Z’s then-newly-acquired streaming platform that promised artists more profit for their music.

Later that summer—and amid label issues—Wayne dropped The Free Weezy Album through Tidal. It was yet another stop gap between The Carter V, which still wouldn’t be released for over three years.

November 2016: Wayne calls himself a Roc-A-Fella millionaire

It’s still unclear what, exactly, Weezy meant here, but during his set at Tyler, the Creator’s 2016 Camp Flog Gnaw Carnival, he called himself a “Roc-A-Fella millionaire.” It could mean that he had arranged a new partnership with himself and Roc Nation Management or the Roc Nation label division which he appeared to confirm months later…

April 2017: Weezy declares himself part of Roc Nation

During a Pennsylvania concert, Weezy officially declared himself a member of the Roc Nation squad, though, it was still totally clear what that meant. He sure seemed excited, though. "Is it cool if I just say it?” Wayne said before throwing up the Roc sign. “It’s the Roc. You know I'm a member of that team now. We’ll talk about that later, though,” he said.

December 2018: Wayne says Jay-Z helped him with $14 million tax debt

During a stop of his I Ain’t Shit Without You Tour in 2018, Weezy took a moment to give props to other rappers who helped him along the way. Among them was HOV, whom Weezy said helped him out of some serious tax problems.

"There's people like Jay-Z. He helped me out when I was really, really, really down. Really, really, really down. There's people like Swizz Beatz who's gonna send me every single beat he make and wants me to rap on every single one until I got my situation straight," the rapper told the crowd. "Jay don't want me to tell nobody. That man helped me with my taxes. He's a real friend, y'all."

May 2019: Weezy calls Jay the greatest rapper of all time

While doing some promo for Bumbu Rum in 2019, Weezy listed Jay as the greatest rapper of all time. "1 yr later...@originalbumbu🐐 Who’s the GOAT to you? I got Jay! Drop names in my komments⚰️,” he wrote in a social media post.

September 2024: Nicki Minaj goes off on whoever chose Kendrick Lamar to headline the 2025 Super Bowl over Weezy

If we’re being honest, you can always count on Nicki Minaj being more than a little messy, and she lived up to that reputation with a series of tweets she posted after Kendrick Lamar and Jay-Z announced K-Dot as the headlining performer at the 2025 Super Bowl.

"One nigga took a knee The other nigga took the bag. He gon get you “niggers” in line every fkng time" Nicki tweeted in one part of a barrage of vicious tweets. "Got everything in the world. Still spiteful & evil. Disgusting. Be happy Abeg. Go be fang happy nigga!!!!! In rap business. In women business. When you got the politicians & the police you good tho. Plus dat ugly laugh taffy alien."

For his part, Birdman also spoke on the matter through social media, posting, “These niggaz Pussi @NICKIMINAJ @Drake @LilTunechi YMCMB. I’m make these niggaz respek us on Gladys,” onto X Monday.

Speaking on his sports talk show It Is What It Is, Cam’ron, who’s had his own issues with Jay, made his own weighty assertion: “It’s one person who’s stopping this. It’s not really a secret,” he continued, albeit without naming names. “Lil Wayne had a problem with somebody before who’s kinda part of the organization running it. This is payback. Who’s Lil Wayne’s artist? Drake. This is crazy, bro. It’s ridiculous.”

On the latest episode of his podcast, Joe Budden also insinuated this was a calculated Jay move, hinting that it was get back at Wayne’s mentee Drake.

Whatever is going on, don’t expect the back and forth between Jay and Wayne to end anytime soon.