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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  • superunknown

    how many errors can an article have and still be published?

  • G5TY

    you forgot the the live mtv interview #classic

  • RIP YE

    Ye’ Just lost it last couple years. Everything was normal until “COLD” came out. Son of a bitch, I never thought it was true but I gotta Blame the Kardshians.. No other explanation…..

  • Mosa

    I am trying to figure out why Kanye wants the world to view him like he views himself. Does he not know that it’s okay for other to see him as I do, an egotistical, self-absorbed, “rapper” with a big anger problem and obsession with his fiance. The man seriously lost it after his mother passed and having lost my own mother I can see how. I haven’t been the same since either, the difference is, he is in the spotlight. . he can make a bigger a** of himself in the public eye at his own expense.

    Has it dawned on him that his recent public meltdowns and antics is why no one outside of music is trying to fux with him. Did he even see his fashion line? LOL laughable and the only people who liked it were his fans who couldn’t see how flawed his designs were. Kanye thinks that being rich means he can do whatever and in a sense, yes it does, but there are still some things in life that you have to have actual skill, knowledge, and talent to do such as being the kind of designer that he wanted to be. He wants to be an McQueen or a Versace but without an ounce of training, skill, research. . .money can’t buy you everything Ye!!

    I don’t know if he is scared of being forgotten or what but he needs to chill on the public rants and just enjoy that adorable baby and get married to his fiance and live life. The world is not going to love him. . .I don’t and never have but it’s okay and I wish someone would tell him that. I wish someone would give this man a hug, hug him tight and whisper in his ear that, “It’s okay. . .Donda is very proud of you and always will be”

    • DarkGambi

      “you have to have skill, knowledge, and talent”…You acting like Kanye was born rich lol do your research before you start ranting, everyone knows Kanye’s from the slums of Chitown. He’s the most talented artist in the past 10 years, and a trendsetter. Oh and whats wrong about Kanye being obsessed with the girl of his dreams?

      • MacDre

        Everything he did in the music world has nothing to do with Fashion though. For as long as i’ve known about kanye west his fashion/style was just wearing popular brands like gucci, louis, bape.

      • MacDre

        Everything he did in the music world has nothing to do with Fashion though. For as long as i’ve known about kanye west his fashion/style was just wearing popular brands like gucci, louis, bape.

      • Shay_Knight

        She already acknowledged his abilities as a musician. She was referring to the “skill, knowledge and talent” it takes to make it as a *designer. Just because someone can sellout arenas for a concert doesn’t mean they can sellout clothes from retail stores. Just ask Beyonce and House of Dereon. Quality product is a craft, not a “look at what else I can do” hobby.

      • abel

        Kanye is not really from the slumps he wasn’t rich but either was he poor his mother was a college professor in Atlanta than in Chicago so you should be the one doing the research, and on the girl of his dream well is sad that he dreams so low

        • DarkGambi

          Ya I know, but I exaggerated a little to prove a point. And whats wrong with Kim K? She got her own cash and she’s sexy..what more could a guy ask for!

          • abel

            a girl that’s not a hoe

          • Sloth™

            ummm…. do u even know how she got her entitlement? Shr became famous from a sex tape, cheated on BOTH husbands, and dated SEVERAL guys back to back. how is she not a hoe?

          • abel

            did I said she wasn’t?? I said that’s his dream girl and if he loves her et him love his girl won’t be the first famous dude to love a girl like her

          • abel

            but hey he likes her like that and is his dream girl not mine so there’s really nothing wrong with that

    • abel

      kanye should read this

    • mike

      MOSA has made the most accurate comment on here!

  • Constantine The Emcee

    I’m lost, this sounds like some regular I can vent cause this my homie moment, and Sway was like this is a professional interview this my business don’t embarass us,
    then Ye’ apologized…I’m confused…

  • Cocaine Howie

    Starting to care less and less about Ye each day.