The most unwittingly funny boasts in hip hop history

Written by Nathan Jolly on 29th June, 2018
The most unwittingly funny boasts in hip hop history

This morning while heading to work, we were listening to Notorious B.I.G’s Greatest Hits and laughing at one of his less-than-successful boasts, which you’ll read about below. This started a conversation about how a lot of the posturing on hip hop tracks comes across as unwittingly hilarious.

Below are the funniest ones I could recall off the top of my head, because deep research is for suckers.

Enjoy, and feel free to add to the list in the comments; like our list of the least rock ‘n’ roll words used in rock songs, this is a living document and the good work is never done.

Juicy – Notorious B.I.G. 


“Phone bill about two G’s flat

No need to worry, my accountant handles that.”

Translation: I signed a prohibitively expensive phone contract, and you better believe I am making long-distance calls, returning calls after being paged (often at 5:46am), and copping excessive roaming charges for my brick mobile phone. Car phone? You better believe it. #ThugLife. I am paying for this, but my accountant settles the bill, despite letting me know passive-aggressively that perhaps I should reconsider my phone habits.

Forgot About Dre – Dr Dre and Eminem


Hated on by most these niggas with no cheese, no deals and no G’s

No wheels and no keys, no boats, no snowmobiles, and no skis

Translation: Why would I pay attention to negative energy from someone who is so unsuccessful that they don’t even own a snowmobile, nor a pair of skis to shred the white powder after said snowmobile has gotten me to the top of whatever ski run I happen to be holidaying at ‘cos I’m from the streets of C-C-Compton.

Gin and Juice – Snoop Dogg(y Dogg)


Two in the mornin and the party’s still jumpin

cause my momma ain’t home

Translation: I still live with my mum, and believe that a party that stretches until the modest hour of 2am is somehow a wild, “jumpin” occurrence. That’s some gangsta shit!


Fuck Wit Dre Day – Dr Dre


Gap teeth in ya mouth so my dick’s gots to fit

Translation: Guess who’s back? Back again. I am either fucking someone who is so toothless that I can insert my dick between the sizable gap, or I have a micropenis that can fit between a single gap between two front teeth. Either way, I need to rethink this boast/insult.

The Motto – Drake and Lil Wayne


Seven, grams in the blunt

Almost drowned in her pussy so I swam to her butt

Translation: Much like Dre above, I need a tighter gap in which to place my appendage. A vagina simply wasn’t doing the job. I was drowning in it, as stated.

Insane In The Brain – Cypress Hill


Bro, I got ta’ maintain

‘Cause a nigga like me is goin’ insane

Insane in the membrane

Insane in the brain!

TRANSLATION: If you mess with me, I am going to go loco, and this particular insanity will be located in the membrane, which is a pliable, sheet-like structure which acts as a boundary/lining in an organism. In other words, I have a nasty skin rash. You got me fired me, and now I am flushed.

What’s Love – Fat Joe, Ashanti, Ja Rule


Woo! Yeah, slow down baby

Let you know from the gate I don’t go down lady

TRANSLATION: I may be morbidly obese, unattractive, and fiercely misogynistic, but at least I won’t pleasure you, orally. I promise.

The article was originally published on The Industry Observer

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