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Awkward Moments in Hip-Hop History – XXLMAG.COM

There is no way to escape an awkward moment, no matter who you are. In hip-hop, rappers have been involved in plenty of mortifying experiences that have been caught on camera.

Who can forget Kanye West’s infamous moment in September of 2005, during the live broadcast of the Hurricane Katrina telethon, A Concert for Hurricane Relief? Kanye calling out then-president George W. Bush live on air is undoubtedly one of the most awkward, yet amazing moments in hip-hop history.

There have been plenty of these moments at award shows, too. At the 2020 Oscars Awards ceremony, Eminem’s surprise performance of “Lose Yourself” left some audience members stone-faced except for snoozing film director Martin Scorsese, which became a viral moment. Rapper Lil Mama crashing Jay-Z and Alicia Keys’ performance of “Empire State of Mind” at the 2009 MTV Video Music Awards is also one of the more awkward moments in rap history.

Some rappers have even had interviews that went left, making for a moment that wasn’t planned. Cardi B had one at the 2018 Grammy Awards when she spoke honestly to E! News reporter Giuliana Rancic about her nervousness of being a first-time Grammy nominee. Birdman‘s awkward 2016 interview with The Breakfast Club needs some “respek” on this list, too. And when fellow rapper Tyler, The Creator hit up Hot 97 to freestyle for Funkmaster Flex, the moment featured Tyler spitting wild lines about Flex.

In the end, awkward situations are just another part of life. So XXL highlights some of the Most Awkward Moments in Hip-Hop History.

  • Kanye West Crashes Taylor Swift’s VMAs Speech

    The 2009 MTV Video Music Awards will forever stand out as having one of the most awkward moments in hip-hop history involving Kanye West and Taylor Swift. While the pop singer was accepting her award for Best Female Music Video of the Year, beating out fan-favorite Beyoncé’s “Single Ladies” visual, Kanye quickly hopped on stage to crash her speech.

    As Swift looked on bewildered, West stated, “Yo, Taylor, I’m really happy for you. I’ma let you finish, but Beyoncé had one of the best videos of all time. One of the best videos of all time!” This was super awkward, especially when the camera panned to Bey’s face.

  • Iggy Azalea Spits a Freestyle and Fails Miserably

    A rapper should have the ability to freestyle off the top of the head. Some can do it, but some can’t. Iggy Azalea falls in the latter. On June 13, 2013, the Aussie rapper appeared on Sway in the Morning for a standard interview. Near the end of their discussion, Sway asked Iggy for a “hot 16.” She obliged him with an a cappella freestyle that was less than stellar.

    As one caller puts it, it was straight “trash.” Not only was Iggy’s freestyle moment awkward for Sway and everybody in the room, it also became the funniest meme of 2014.

  • Lil Mama Crashes Jay-Z and Alicia Keys’ VMAs Performance

    In a shockingly awkward moment at the 2009 MTV Video Music Awards, Lil Mama crashed Jay-Z and Alicia Keys’ show-closing performance of their New York City anthem “Empire State of Mind.” Lil Mama was sitting two rows away from the stage and was so inspired by Hov and Keys’ performance that she wanted to join in on the action.

    At the tail end of the performance, Lil Mama walked onstage and stood awkwardly beside Jay and Keys in a B-girl stance as the crowd looked on bewildered. Afterward, she apologized for the stunt. “I did not mean any disrespect,” she said in a statement.

  • Tyler, The Creator’s Wild Funkmaster Flex Freestyle

    On July 25, 2019, veteran Hot 97 personality Funkmaster Flex was on the receiving end of Tyler, The Creator’s trolling during a freestyle session on his radio show.

    Tyler began spitting sexually-charged rhymes (fast forward to the 1:20:21 mark) about anal sex. “Me and Flex looking in the index/For buff net niggas just for some hot butt sex,” he nonchalantly raps.

    Flex’s reaction to the line is hilarious. When Flex stops Tyler and asks, “What made you go with that verse?” the awkward pause between them is so palpable you can feel it.

  • Reactions to Eminem’s Oscar Performance

    Seventeen years after winning an Academy Award for Best Original Song for “Lose Yourself,” Eminem made a surprise appearance at the 2020 Oscar Awards ceremony in February to perform the 8 Mile track.

    You would think Em rocking the mic at the Oscars would excite the actors and everyone else in attendance. Nope. While celebrities like singer Billie Eilish and actress Idina Menzel appeared to be confused by it all, Martin Scorsese’s reaction of him nodding off during Eminem’s performance was priceless. Then, of course, his reaction became a meme. So much for losing yourself at the Oscars.

  • The Game Dumped on Change of Heart

    Before The Game became a chart-topping rapper, he was awkwardly dumped on an episode of a 1990’s dating show called Change of Heart. A then-18-year-old Game was granted an opportunity to date a female contestant named Arana Benson to see if he will have a change of heart or stay with his then-girlfriend, Sadita.

    Although Game had a great date with Arana, he opted to stay with Sadita, but she had a different plan. His former flame had a change of heart and picked her date over Game, much to his chagrin. The look on the rapper’s face after he got dumped said it all. Awkward!

  • Eminem Gets the Butt of Bruno’s Joke at VMAs

    Eminem rarely attends awards shows. The reason why that might be may have to do with what happened during the 2009 MTV Video Music Awards. While the Detroit rhymer was sitting in the audience enjoying the festivities, comedian Sacha Baron Cohen, as his character Bruno, dressed in white feather wings and a jockstrap, landed upside down in Em’s lap with his butt to his face.

    Eminem stormed out of the venue leaving attendees and viewers at home in shock. Later, Em revealed that it was all a gag. He reportedly went back to his hotel room and laughed for three hours.

  • Kanye West Makes Shocking Statement During Hurricane Relief Benefit

    On Sept. 5, 2005, Kanye West made a statement that shocked television viewers watching celebrities do their part in helping displaced families following the aftermath of Hurricane Katrina in New Orleans. During a live broadcast of A Concert for Hurricane Relief, a celebrity-driven telethon, ’Ye called out then-president George W. Bush, who the rapper felt was doing nothing in a moment of crisis.

    While standing next to funnyman Mike Myers, Kanye deviated from a prepared script on the teleprompter and infamously said, “George Bush doesn’t care about Black people.” The look on Myers’ face is priceless. But Chris Tucker’s deer-in-headlights reaction makes this one of the most awkward moments in hip-hop history.

  • Drake Gets Booed at Camp Flog Gnaw Carnival

    Drake is a top-tier performer. So it’s very rare that he gets booed, if ever. On Nov. 10, 2019, Drizzy faced his toughest crowd yet. While making a surprise appearance at Tyler, The Creator’s Camp Flog Gnaw Carnival, he was met with a scattering of boos from the audience during his performance.

    After realizing the crowd wasn’t feeling him he exited the stage. “It’s been love. I love y’all,” he said before walking off. Afterward, in a Rap Radar interview, Drake acknowledged the audience was booing him. However, he understood that the fans were hoping to see Frank Ocean grace the stage, but instead, they got him. An awkward situation indeed.

  • Nicki Minaj Calls Out Miley Cyrus at VMAs

    Nicki Minaj doesn’t tolerate disrespect. So at the 2015 MTV Video Music Awards, Nicki called out Miley Cyrus for disparaging comments she made about her a few days before the ceremony. Nicki stole the show (and inspired memes and a new catchphrase) with her single verbal jab: “And now back to this bitch that had a lot to say about me the other day in the press. Miley, what’s good?”

    Miley, who was hosting the VMAs that year, played it off, but it did get a little awkward while watching what went down. Luckily, cooler heads prevailed and Miley didn’t get dog-walked by Queen Barbz.

  • Jim Jones Gets Emotional on Hot 97

    In an emotional Feb. 9, 2017 interview with Hot 97 radio personality Funkmaster Flex, Jim Jones talks about his loyalty to Cam’ron during Dipset’s rise in the 2000s. At one point, the Harlem rapper begins crying as he explains a fight at Rucker Park, in which Cam left Jones to defend himself against dozens of people (at the 15-minute mark).

    “There’s never been a time I never back down from a situation, except God,” he stated. “And I’ve been up against 20, 30 deep by myself when niggas left me by myself. And I escaped those situations and still come back and give niggas high-five.” This was a very emotional interview, but also awkward since we’re sure even Flex didn’t expect Jim to let the tears fall.

  • Lil Uzi Vert’s Awkward Interview at 2018 Grammy Awards

    At the 2018 Grammy Awards, Lil Uzi Vert hit the red carpet and did his round of press interviews. In his chit-chat with E! News reporter Guiliana Rancic, the Philadelphia rapper appeared to be shy at first. He would eventually open up to Rancic and that’s when things got awkward. Rancic tried to get a sense of Uzi’s excitement for being at the Grammys but got no emotion from him. When Rancic asked, “What’s next for you?” Uzi replied, “Waking up, eat some Pop Tarts.” Rancic’s puzzled look at his answer was priceless.

  • 50 Cent’s Missed Kiss With Reporter Erin Andrews

    On Feb. 24, 2013, 50 Cent went to the Daytona 500 in Florida and garnered media attention from the appearance due to an awkward moment with reporter Erin Andrews on the pit walk before the race. 50 greeted her and went in for a kiss on the cheek, but she turned her head and dodged his lips. Oops, awkward.

    TMZ eventually caught up with Andrews and she took responsibility for her and Fif’s embarrassing kissing mishap. The former ESPN reporter claimed that she was focusing on getting an interview with racer Danica Patrick and not paying attention to 50.

  • Canibus Breaks Out a Notepad During Rap Battle

    Back in 1997, Canibus engaged in a memorable rap feud with LL Cool J that has now become hip-hop folklore. But decades later, in July of 2012, Canibus created another memorable moment at a Los Angeles rap battle against rapper Dizaster and did the unexpected.

    During the battle, Canibus pulled out a notebook to recite rhymes and the air of excitement quickly left the room. As anyone knows, rappers reading lyrics from a book is frowned upon. “You may have not seen an amazing battle, but you saw something you never expected, and it was 20 times more interesting,” Dizaster told LA Weekly. Canibus never recovered from that awkward moment in rap battle history.

  • Birdman Looks for “Respek” in The Breakfast Club Interview

    Four years ago, Birdman was at the highest level of pisstivity when he made a very brief appearance on Power 105.1’s popular morning radio show The Breakfast Club. The Cash Money head honcho was visibly angry over hosts Charlamagne Tha God, Angela Yee and DJ Envy’s past comments about him and he let it be known.

    “Stop playing with my name,” he warned the trio. Birdman then added, “When y’all saying my name, put some respek on it.” The awkward back-and-forth between Birdman and the hosts became a viral meme and the shortest interview in The Breakfast Club‘s history.

  • Cardi B’s Awkward Red Carpet Interview at 2018 Grammy Awards

    At the 2018 Grammy Awards, Cardi B had a painfully awkward interview with E! News reporter Giuliana Rancic on the red carpet. Bardi, who was nominated for two rap awards for “Bodak Yellow” at the event, expressed her nervousness as a first-time Grammy nominee. When Giuliana asked Bardi how she was doing, Bardi responded, “I’m feeling good. I’m feeling nervous, overwhelmed, everything. Butterflies in my stomach and vagina.”

    The interview got a little weird as Rancic tried to remember a Bardi line in “Motorsport.” Cardi B’s look of being somewhat puzzled at what was being explained to her made it all the more awkward.

  • Vanilla Ice Gets a Cold Reception on The Arsenio Hall Show

    The Arsenio Hall Show had plenty of memorable interviews, but one of the most awkward sit-downs on the show came when Vanilla Ice was a guest on Feb. 15, 1991. The “Ice Ice Baby” rapper, dressed in a metallic jumpsuit, was on the defensive as Hall grilled him about his background and his alleged remarks about MC Hammer.

    When Ice brought out Flavor Flav for an on-camera hug, that’s when Hall snapped. “That’s why you brought him out to show that you have Black supporters?” he asked. Hall’s cantankerous interview with Ice may have backfired because his usual adoring studio audience actually booed him twice.

  • Nicki Minaj Accidentally Exposes Her Breasts on Live TV

    Nicki Minaj had an awkward moment while performing on Good Morning America on Aug. 5, 2011. During the rap star’s performance of “Where Them Girls At,” her left breast fell out of her bra. For the people in the front row (and the East Coast viewers who saw it live), it was a surprising moment, but for Nicki, it was awkwardly embarrassing. In the clip below (fast forward to the 1:17 mark), you can’t see Nicki’s wardrobe malfunction, but you can see her walking away and being mortified by the fact that she was exposed. Despite her embarrassment, Nicki continued to perform like a trooper.

  • Tyler, The Creator Walks Out of Tim Westwood Interview

    Tyler, The Creator doesn’t do many interviews these days, so when he does take part in a Q&A, it’s always a spectacle. On July, 11, 2011, during an interview with legendary U.K. DJ Tim Westwood, Tyler, donning a cast after breaking his foot, appears to be aloof when responding to Tim’s questions.

    At the 4:13-mark, things get weird when Tyler turns the tables and interviews Tim. Suddenly, the DJ does a plank behind Tyler and in a huff, the Goblin rapper takes off his jacket and hops out. Tyler eventually comes back and the interview gets even more awkward and weird.

  • Joe Budden Confronts Consequence at Hot 97

    VH1’s Love & Hip Hop New York is known for drama and sometimes the drama spills outside of the show. On Feb. 5, 2013, after Consequence talked about his perceived beef with Joe Budden and Raqi Thunda in a previous interview, Budden ran up on Cons at Hot 97. In the video above, you can see then-radio personalities Cipha Sounds and K. Foxx sit awkwardly next to Peter Rosenberg who was in the middle of the action. Budden is very calm as he questions Cons about his alleged remarks about him and Raqi. Thankfully, cooler heads prevailed and no punches were thrown.

  • Crowd Boos Dr. Dre and Snoop Dogg

    The Source Awards were held in New York on Aug. 3, 1995, and there was plenty of awkward and controversial moments at the event. One of them was when Dr. Dre accepted his trophy for Producer of the Year. While walking up to the stage, Dre was met with boos from the audience. Snoop Dogg, not liking the reception he and Dre received, grabbed the microphone and yelled, “The East Coast ain’t got no love for Dr. Dre and Snoop Dogg?” As the boos got louder, Snoop responded, “We know where the fuck we at! East Coast in the muthafuckin’ house!” This was an awkward, yet very intense moment at the ceremony.

  • Mike Tyson Calls Eminem the N-Word

    Eminem appeared on Hotboxin with Mike Tyson’s podcast for a 49-minute interview that got a little awkward near the end. Before Tyson wrapped up the interview, the legendary boxer praised Em for his notable accomplishments and he dropped the N-word on him. “Everything you got was, fuckin’, not even given to you,” he said. “You fuckin’ slaved for it, you know what I mean? You’re the only White guy that knows what it’s like to be a nigga.”

    Em nervously responded, “Not sure how to answer that.” At that moment, you could feel the awkwardness in the air between Iron Mike and Slim Shady.

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