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Cockiest Rapper?

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GangstaBoogy:
50 Cent

"I wanna apologize to all the rappers that didnt make any money this year...and I just wanna let u know - its not gonna get any easier"

"dont call me to feature, I dont wanna rap with you"

P Nelson:
Dr Dre... Knocturnal but it doesent sound good.. Jay Z and many others

Bramsterdam (see ya):
imo 50 is pretty cocky..

On The Edge of Insanity:
Big L was hella cocky, but he actually had shit to brag about cause he was actually dope.

And as well as Slick Rick you can't forget Big Daddy Kane, he used to be real cocky, and also Rakim is too, always refering to himself as the god.

Trauma-san:
I still say nobody yall mentioned is close to the Ruler.  50 Cent ain't even close, he's cocky, but Rick was just unbelievably cocky, lol.  

"Even Chandaliers are jealous over Patch Eye's Glitter"

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