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Lamest brags in a rap song

Lunkhead

...and rise again!
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There's a lot of cringey lyrics in rap. One of the gayest lines I ever heard was a Nas lyric in the Mobb Deep song "It's Mine":

Silk shirts on my chest show what a flirt
Halle Berry blew a kiss at the Barbara Streisand concert

Why are you at a Barbara Streisand concert, you homo?

There's a line in House of Pain's "I'm a Swing It" where Everlast says

'Cause I can feel it in the air tonight
But yo I'm not Phil Collins
I'm more like Henry Rollins
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Why would you pick an even bigger faggot than Phil Collins to compare yourself to?
 
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