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What if Lil Wayne had signed with Jay Z in 2005?

Source: AintNoJigga
Around 2005-2006, Jay Z, as president of Def Jam, made a play to sign Lil Wayne. It never eventuated. Jay's side of the story, told to The Breakfast Club in 2013, places the blame for the failed deal squarely on the table of Birdman, the head of Cash Money Records, the label that discovered and signed Wayne. Jay claims Birdman sent him a letter for "torturous interference", and that was that. Lil Wayne explained in 2016 that he had indeed taken a daytime meeting with Jay at a 40/40 club in the mid-2000s, but the $175k value of the deal wasn't agreeable: "Believe that... I was looking like... two teeth in my mouth is 175. My bottom teeth."

2006 was the beginning of Wayne's run as the greatest rapper on the planet. He ran the genre from 2006 through at least 2008, releasing an unprecedented amount of critically acclaimed music. As Jay said on 2009's "A Star Is Born", "Wayne scorchin', I'll applaud him / If he keep going, pass the torch to him". But Wayne didn't keep going. His 2009 rock album Rebirth fell on deaf ears, and after his 8-month incarceration that began in 2010, he was never able to recapture the alchemy that saw him entirely untouchable during that halcyon run.

How would Wayne's career have been different, had this illustrious period been under the guidance of Jay Z, and either Def Jam Records or Roc-A-Fella?

Free Mixtapes? Unlikely


While Wayne had no choice but to release Dedication 2 (2006) and Da Drought 3 (2007) for free (although D2 did pop up on iTunes at one point), due to his lack of payment for instrumentals already used by other rappers, there was a wealth of original music released for free between 2006 and 2010. Wayne arguably built his buzz off of mixtapes, notably the Squad Up series in the early-2000s, which signified his coming of age as a lyricist and true technician. But it doesn't hide the fact that his three critically acclaimed mixtapes (D2, DD3, No Ceilings) had 20-30 of the hottest verses he would ever spit, all for free.

Jay Z doesn't give things away for free. Even his own critically acclaimed mixtape, the S. Carter Collection, was designed to boost his bank balance. It came packaged with his the sneaker collaboration he'd forged with Reebok, one that attained huge, unrivalled success. Freestyles get recycled and thrown onto album tracks, or used to promote the albums of his own artists (think "Dear Summer" on Memphis Bleek's 534, or his "Grammy Family Freestyle" appearing in full HD with a Chris Martin feature). 

Notice that the majority of Jay's artists don't put out mixtapes. Beanie Sigel didn't release a mixtape until he was under Dame Dash. Bleek waited till 2005, and self-released free music. Young Chris didn't release a mixtape until 2007, post-Roc-A-Fella. Neef Buck released one mixtape while signed to Roc-A-Fella, though under his own label. J. Cole has released 2 mixtapes under the Roc Nation label, the second was released commercially and charted at number 7 on the US albums charts, and the first was re-released in 2013 commercially. 

It's unclear how Jay would have navigated this situation. Likely, he'd urge Wayne to hold some of those incredible verses back, to be used on even more guest spots or for future albums. A large part of Wayne's success during this incredible period was due to his mixtapes, and the fact they were free ensured they spread across the internet like wild-fire. But did Wayne burn too brightly? Did he spread himself too thin? Would he have improved his longevity if he held some of that music back? 

The only time Jay and Wayne have since linked up for a full project (they have collaborated on 3 individual tracks) was the Free Weezy Album in 2015, a record Wayne intended to release for free, but ended up a Tidal streaming exclusive, securing a revenue stream from an album that wouldn't have made any tangible income. 

Quality Control ("Pussy Monster"?!)

"I just make the records, Tez picks the songs." Tez is Cortez Bryant, Wayne's long-time manager and A&R. As Tez said in that interview: "Wayne is like 'I'm a just create it and give it to you and you do what you do with it'". So this means he's accountable for "Pussy Monster" appearing on Wayne's near-classic Tha Carter III, or "Wowzers" on IANAHB2, and relegating "Mirror", Wayne's incredible collaboration with Bruno Mars, to the deluxe edition of Tha Carter IV. 

Someone should have stepped in before Wayne released his 2009 rock album Rebirth. While it wasn't terminally bad, it was an early example of the inconsistency that has now become his most frustrating quality as an artist. He followed up the incredible, million-in-a-week Grammy nominated Tha Carter III with the worst album of his career. 

Jay Z did rock as well. Twice on 2002's The Blueprint 2 he indulged in guitar-based music, on "A Dream" and "Guns & Roses". He also partook in a genre-busting collaboration with Linkin Park for 2004's Collision Course, an EP that shot to number 1, went platinum, and sold 3.5 million copies worldwide, along with widespread critical acclaim. 

Now, imagine if Wayne had saved the two best tracks from Rebirth, "Prom Queen" and "Drop The World", and placed them on his 2010 record I Am Not A Human Being, released to keep his buzz up while he was behind bars. "Prom Queen" hit number 15 on the US Billboard 100, and would have made a brilliant mid-album palate cleanser. Instead, Wayne has a record in his discography that sits at 37/100 on Metacritic. Jay Z would never allow this to happen. 

Leaks (or how Lance Rivera learned to stay away from Kit Kats)

Source: AintNoJigga

Yeah, Jay Z doesn't much like leaks. In 1999 he was arrested and charged with stabbing label CEO Lance "Un" Rivera at the Kit Kat Club. Jay pleaded guilty, and skated with probation. It's believed Jay and his team attributed a month-early leak of his 4th studio album Vol. 3... Life and Times of S. Carter to Rivera, and dealt retribution. 

Although Jay's music would leak again, it would never be on such a scale. Lil Wayne suffered more than almost anyone else from the actions of a bootlegger. The offending party was DJ Empire, who leaked almost the entirety of what was to be Wayne's LP Tha Carter III. Cortez Bryant explained Wayne was hurt, but locked down the studio and created almost an entirely new album, which ended up being some of his best work. 

Overall, 35+ original songs were leaked from these recording sessions. It appeared on the internet as Da Drought Is Over series, but also The C3 Sessions. Wayne would suffer similar leaks before Tha Carter IV, although not to the same extent. While Jay Z's album leaked a month in advance way back in 1999, he wouldn't experience another leak of such magnitude. In 2008 a couple of loosies surfaced, notably "Ain't I", and "Ultra" and "Ghetto Techno" appeared online around this time too. But it's safe to say Jay tightened his circle notably, and that of his artists. Although albums like The College Dropout leaked, no-one on Roc-a-fella lost that amount (more than 35 songs) of high quality original product, ever. 

Who knows what measures Jay Z has in place to combat leaks? But just imagine if Wayne had songs like "Pussy, Money, Weed", "I'm A Beast", "Did It Before", "Kush", "La La La", "Something You Forgot" and "Love Me Or Hate Me" in his arsenal, ready to be deployed any time his career took a slight dip (during his incarceration, for example)

Wayne Would Never Need To Sue

During Cortez's Rap Radar episode it was revealed Cash Money was paying Wayne all the way up until 2014's "Believe Me" dropped. They waited for the money from the label, and it never arrived: "This time when we put it out, the check didn't come." The hugely successful Drake Vs Wayne tour began, then concluded, and Wayne's team wanted to put his next studio album, Tha Carter V, out immediately to capitalise. Still, Cash Money couldn't come up with the cash money.

Roc-A-Fella has been accused of owing former artists money. In 2010 Beanie Sigel went on record saying Dame Dash "owe me some money... My own lawyer found about $11 million that Dame stole from me". Oddly, Oschino, a member of the Roc group State Property, told The Breakfast Club in 2016 it was Beanie who owed them money. And while Dame Dash has been dogged by claims that he "owes everyone", it's incredibly rare to hear anyone level that claim at Jay Z. Beanie and Jay made up at the Tidal B-Sides concert in 2014, and Jay remains on good terms with Young Chris, Memphis Bleek, and just about everyone except Jaz-O. 

There are no parallels between what Birdman is currently doing to Lil Wayne, and what Jay Z has done to any of his artists, ever. Doubtless, if Wayne had signed with Jay in the mid-2000s, his bank balance would truly reflect his sales and standing in the industry. 

Young Money

Young Money Entertainment was formed in 2005, believed to be a sweetener to help convince Wayne to re-sign with Cash Money Records for an extended period of time. The label has 11 number 1 albums in their discography, and two of the biggest artists in the world, Nicki Minaj and Drake, are currently signed to the label. 

If Wayne expressed a desire to create his own label while signed to Jay Z, things would have taken a similar path. On 2011's "Why I Love You" Jay rapped "I tried to teach n***s how to be kings / And all they ever wanted to be was soldiers", with regards to artists like Beanie Sigel who didn't share Jay's entrepreneurial mindset. He allowed Memphis Bleek to create Get Low Records during the late 90s, Kanye West formed G.O.O.D. Music, and J. Cole has Dreamville Records. 

It's hard to say if anything would have been different. Young Money is wildly successful, but they may have been able to hang on to Tyga if YM was a part of Roc Nation or Def Jam, because he'd actually have been getting paid. 

Lil Wayne's Legacy

On Jay's 1999 track "Pop 4 Roc" he made the bold claim "You are about to witness a Dynasty like no other". Under Jay's watchful eye, at least 2 legends have been made. Both Kanye West and Just Blaze were relative unknowns before they began their Roc-A-Fella careers. In 2017, Kanye is at the absolute pinnacle of both hip-hop and fashion, and Just Blaze is considered a legendary producer. Jay also signed a 16 year old Rihanna, and gave guidance and opportunity to Ne-Yo and J. Cole, not to mention signing Rick Ross to Def Jam.  

Lil Wayne, in terms of ability and potential, was quite possibly on-par with Kanye West and Rihanna, and has proven himself to be an all-time great. Alas, Wayne fell off. His fall seems harder than most becauseit came and went so quickly; he arrived in 2006 and ran with it until 2010, but with the ability he had, he should still be sitting on top of the world. 

Would this have happened under Jay Z's guidance? How many rappers or artists have actually fallen off on Jay's watch? He managed to bounce back himself from the poorly received 2006 record Kingdom Come. Foxy Brown left Jay's orbit in 1997 to work with Nas and AZ, and fell off in the early-2000s far removed from Roc-A-Fella. Memphis Bleek was always "one hit away". Beanie Sigel went to prison. Kanye West never fell off, Just Blaze never fell off, J. Cole hasn't fallen off, Rihanna hasn't fallen off. There's a reason why everyone is signing management deals with Roc Nation: The label doesn't lose. Artists don't flop when they're signed to Roc Nation. Albums like IANAHB2 don't exist in their discography. mixtapes like No Ceilings 2 just don't happen on Jay Z's watch. 

I will make a bold claim. Lil Wayne would be comfortably in most people's top 5 if Jay Z had been in charge of his career since 2006. Rebirth would never have been a full project, "Wowzers" would be in a hard-drive somewhere buried deep underground. Wayne would never have attempted to rap over "My Name Is", or if he did, it would have been destroyed before anyone outside the studio heard it. Jay Z doesn't flop, he never has. Even Kingdom Come went number 1 and sold 680k first week. It has a Metacritic score of 67, 37 higher than Rebirth and higher than IANAHB2, Tha Carter IV, S4TW, D4, and S4TW2. Wayne's average career score is 60, Jay's is 73. As Jay said:
I've been winning so long it's like alchemy 
Wayne deserves to be in your top 5. It's just a pity it might now be too late to salvage his full legacy (he will still retire as a true GOAT, and maybe, in a few decades time, be recognised for the technician and superstar he is). Hopefully, he manages to secure his bank balance and curb his drug use. Jay Z can help, he always does. 


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