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A History of Kanye West And Sway’s Relationship


Kanye West and Sway Calloway go way back.

In the earl 2000s, when Kanye was still exclusively behind the boards, it was an MTV special, You Hear It First, that first introduced him to the world. And it was Sway who hosted that special. Since then, the two have talked publicly numerous times—either on MTV or on Sway’s morning radio show—with varying degrees of friendliness. Recently, the two’s relationship has seemingly gotten more irritable, with Kanye going as far as to claim that he bought Sway’s first TV. When it’s all said and done, they’re probably more longtime friends who push each other’s buttons than actual enemies, but it’s sometimes a little hard to tell. XXL decided to put together a timeline of the two’s relationship:


Kanye and Sway on MTV’s You Hear It First (2002)

Following the success of Jay Z’s The Blueprint, which Kanye produced multiple tracks on, MTV decided to pick him for You Hear It First, a show that spotlighted upcoming artists. During the episode, Sway, who was hired by MTV only a year or two before, described Kanye as a “more conscious” rapper than other artists on Roc-A-Fella Records at the time. He also said Kanye was “about to write the next chapter of the Roc-A-Fella dynasty.”


Sway interviews Kanye days before Late Registration is released (2005)

During Sway’s second MTV sit down with Kanye, the pair touched on a variety of heavy topics, including homophobia in hip-hop, his mother and when he was wrongly arrested in his early 20s. As usual, Sway held nothing back and at one point asked ‘Ye a question—whether he was “disloyal” to Jay Z—that actually left him speechless. That’s a pretty tough thing to do.


Kanye revisits the Sway and Tech Show (2009)

‘Ye had been on Sway’s radio show multiple times, but he had never been as famous as he was when he went on it in 2009. As King Tech points out at the beginning of the broadcast, none of the other mega stars—Eminem, Jay Z—who were on the show as youngsters had returned back to it. Only Kanye came back to do the show again, which could have been viewed as a favor to Sway.


Sway ranks Kanye seventh on the “Hottest MCs” list and Kanye gets angry (2013)

Earlier this year, Sway, along with a panel of hip-hop writers and personalities, ranked Kanye number seven on MTV’s “Hottest MCs List.” Kanye did not like this. He called into Angie Martinez’ radio show and described why the list was incorrect. Before he hung up, he added, “I just wanted to tell everyone I gave Sway his first TV. And he needs to remember that.” Sway responded by taking said TV on MTV’s RapFixLive and describing the story of how he got it, which involved him going to Kanye’s house back in 2001 and seeing the TV in a bathroom sink.


Kanye and Sway yell at each other on radio (2013)

Maybe it was buildup from the two’s disagreement earlier this year, but both Kanye and Sway got to yelling during their conversation on Shade45. It started when Kanye began talking about how he’s been shunned from the fashion industry, to which Sway then posed the question, “Why don’t you empower yourself…and do it yourself? ” The question set Kanye off. He began yelling at Sway and telling him that he doesn’t know anything about the topic. Eventually, Sway told Kanye to calm down and that he “ain’t gotta turn up” and that their conversation wasn’t a “fucking show.”

After a few minutes, both guys calmed down and apologized to each other. It’s hard to tell what exactly about Sway’s question irked Kanye so bad, but ‘Ye did seem to hint that he’s lost a lot of money—a $13 million figure was thrown out—on trying to start his own fashion line.

Previously: Kanye West Flips Out On Sway During Radio Interview

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