Kanye West Almost Signed With Cash Money

at 1:15 pm | By

kanye west lil wayne 2008 grammys

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Let’s be honest — in the mid to late 2000s hip-hop was dominated by two rappers: Kanye West and Lil Wayne. The two each had built their legacies around this time, whether it was Kanye West’s consistent successful efforts of pushing the sonic boundaries of rap music with each album or Lil Wayne rapping on every single popular instrumental and outmanning the original verse, both emcees defined a generation of fans and inspired some of today’s biggest stars (Kendrick Lamar, Drake, Big Sean, and J. Cole.)

Kanye West made it cool to be yourself and opened the door for non-street rappers to succeed in hip-hop. His sonic influence is still apparent in today’s hip-hop, and let’s not even get into his impact on the fashion tip. Lil Wayne, who we should probably address as mixtape Weezy, changed the way emcees would release music straight to their fans without label approval.

What made their dominance even cooler was instead of acting as rivals, both served as frequent collaborators. Who remembers when Kanye West first experimented with autotune on Lil Wayne’s “Lollipop” remix? How about when the two dropped infamous verses on T.I.’s posse cut “Swagger Like Us.” Don’t forget their “Barry Bonds” collaboration on Yeezy’s Graduation album and the addicting “Let The Beat Build” instrumental West produced for Weezy’s Tha Carter 3 album.


As a hip-hop fan who grew up as a teenager in the midst of the Kanye West and Lil Wayne era, hearing that ‘Ye almost signed with Cash Money back in the day, I can’t help but imagine how different the landscape of hip-hop would be if that ever happened.

Kanye West onstage during the 2015 MTV Video Music Awards at Microsoft Theater on August 30, 2015 in Los Angeles, California

Credit: Kevork Djansezian/ Getty Images

According to Mikkey Halsted, a Chicago rapper who was once signed to Kanye West, ‘Ye had a chance to sign with Birdman. Cash Money came through to Chi-town one time when Yeezy was blowing up and offered him a deal that would sign both him and his artists. Ultimately, Kanye West declined the deal because he felt CM was “too street.” He would go on to sign with Roc-A-Fella instead and the rest is history.

In the interview, Mikkey Halsted also revealed Kanye West addressed the situation on his classic “Last Call” outro on The College Dropout.

“One of my homies that was one of my artists, he got signed. But it was supposed to really go through my production company, but he ended up going straight with the company. So like, I’m just straight holding the phone, getting the bad news that dude was trying to leave my company.”


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