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Top 10 Hip-Hop Grammy Moments

It’s that time of year again and award season is upon us. On Sunday (Feb. 13), fans, artists, industry execs and everyone in between will convene at the Staples Center in Los Angeles, to celebrate the industries top hitmakers on music’s biggest night. With the Grammys around the corner, we here at The BoomBox picked out some of our top hip-hop Grammy moments. From the performances, to the acceptance speeches to the awkward moments on the red carpet, we’re counting down the 10 most newsworthy moments.

Tupac Shakur
Christopher Polk, Getty Images

10. 2Pac Presents Grammy With Kiss

Who says rappers don’t clean up well? Tupac Shakur presented at the 1996 Grammys decked out in a Versace suit alongside legendary rock band Kiss. Although it seemed like an odd pairing, Pac couldn’t look more comfortable with the face-paint-wearing, six-inch-heels-rocking group. In an eerie coincidence, presenting at the Grammys would mark one of his last public appearances before dying tragically later that year.
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Lil Wayne

9. Lil Wayne Pays Tribute to New Orleans

Four years after his hometown was left in ruins by Hurricane Katrina, Lil Wayne took the 2009 Grammy audience back to the catastrophic event, with a performance of his song ‘Tie My Hands.’ Images of the storm’s aftermath played on widescreen as Weezy represented for New Orleans, poignantly spitting a message of hope with the assistance of singer Robin Thicke.
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Jamie McCarthy, Getty Images

8. Kanye Gets Cut Off

Fresh off his fire-breathing, glow-in-the-dark performance of ‘Stronger,’ featuring Daft Punk, Kanye West won the award for Best Rap Album at the 2008 Grammys. But when the “wrap it up” music came on to nudge Yeezy’s speech along, the Chi-town native didn’t take too kindly to being rushed. “Come on, you’re going to play music on me?” West scolded before acknowledging his mother, who died a few months prior, all while warning producers not to cue the music. Even though his mini-freakout made for a bunch of headlines the next day, at least he stood his ground. We salute you Mr. West.
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Kevin Winter, Getty Images

7. Drake, Lil Wayne, Eminem Perform ‘Forever’

Drake may have been a rookie at the 2010 Grammys, but you wouldn’t know it by the way he held his own alongside Eminem and Lil Wayne. Drizzy popped up during the second half of Weezy’s performance to spit a swift 16 from the collaborative track ‘Forever.’ The Toronto native hit the stage and rocked the entire crowd like a seasoned pro. The rapper is set to take the stage again this and he’s nominated for a few awards, as well.
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estelle kanye
Kevin Winter, Getty Images

6. Kanye, Estelle Blast Grammys While on the Air

You didn’t think we’d get through this countdown without showcasing another Kanye moment, did you? The Louis Vuitton Don pulled double duty at the 2009 Grammys, both performing and presenting the award for Best New Artist with Estelle. True to form, West took the opportunity to take a shot at the Recording Academy for failing to include him in the list of past Best New Artist nominees. We’ve gotta give it to Kanye: When it comes to his award show etiquette, at least he’s consistent.
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Christopher Polk, Getty Images

5. Nas and Kelis Make a Fashion Statement

Nas and Kelis popped up at the 2008 Grammys rocking some choice threads on the red carpet. The then-couple both donned the n-word on their clothes in promotion of Nas’ album, which was released that year. While Nas talked up his album’s concept, the real fun was watching interviewers try not to slip up and actually read the words printed on their clothes. Kelis seemed happy to support her hubby, but it wasn’t enough to keep things together, and the couple split the next year.
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50 Cent
Getty Images

4. 50 Cent Interrupts Amy Lee

Long before Kanye became hip-hop’s most outspoken sore loser, 50 Cent took a shot at snagging the title. When 50 lost the Best New Artist award to alternative group Evanescence at the 2004 Grammys, the Queens, N.Y. emcee made sure to get some face time. Just as lead singer Amy Lee started her list of thank-yous, 50 walked past the stage and in front of the camera. Smooth move, 50.
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Ben Gabbe, Getty Images

3. Jay-Z, T.I. Bring ‘Swagga’ to the Grammys

Hip-hop’s biggest stars brought the Grammys “swagga” up a few notches with their performance at the 2009 show. JayZ, Lil Wayne, Kanye West and T.I. hit the stage to perform their track ‘Swagger Like Us.’ Dressed in black tuxedos, the “rap pack” were outshone only by M.I.A., who, being nine months pregnant, was bouncing around in a polka-dot ladybug-inspired getup with her baby bump on full display.
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2. Eminem and Elton John Mend Fences

Eminem attempted to quiet the critics who blasted his lyrics as homophobic by performing with openly gay music icon Elton John at the 2001 Grammy awards. Em and John stood in solidarity performing the song ‘Stan,’ off the Detroit native’s second album, ‘The Marshall Mathers LP.’ To this day, the two remain close friends.
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Ol' Dirty Bastard
Evan Agostini, Getty Images

1. ODB Delivers Muffled Rant

Ol’ Dirty Bastard had something to say at the Grammy Awards in 1998 and he wasn’t gonna stop until he was heard, even if it was at the most awkward moment possible. The late, great ODB took hold of the mic while singer Shawn Colvin attempted to accept her Song of the Year award, and he went off on a hilarious rant. Aside from announcing that his outfit was brand-new, ODB noted that he and the rest of the members of the Wu-Tang Clan should’ve won the Best Rap Album award, which they lost to Puff Daddy.
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