The most awkward moment in hip hop history is definitely...

thesandman

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when lil' mama crashed jay and alicia keys performance a few years back..

Jay's look said it all
 

GETTINIT23

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the 50 cent performance at the bet awards when he advertised viatmin water after a terrible performance was pretty akward
 

Uncle_Ruckus

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when wayne kissed baby on rap city the basement.

Original%20Footage%20Of%20Lil%20Wayne%20&%20Baby%20Kissing%20On%20Rap%20City%20Circa%202002.jpg
 

Grifter

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The look Mannie gives to Birdman calling dudes up to stage for an ass shaking moment.
 

Pop123

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nas performing 2pac's song in front of that crowd, hahahaha. nas never remembers his own lyrics, how the f*ck he gonna be able to perform somebody elses song? even with a teleprompter this n!gga was f*ckin up, hard to watch for a Nas stan like myself. i think 2pacs sister said she was offended because nas didnt know the song, lol, what did you expect? his brain is f*cked up
 

Daniel

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Jim Jones coming out on RapCity with 50 Cent. Was pretty akward too.
 

Pop123

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Jim Jones coming out on RapCity with 50 Cent. Was pretty akward too.

i was hopin 50 was gonna mash him out, just right there in front of the cameras. dipset and g-unit got a lot of liaisons in the street but still, just to send message to cam i was hopin 50 broke his neck on camera
 
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