Coolio's Struggle Braids

[Deleted member 220895]

Not so cool, Coolio. Very uncool of such a notoriously cool dude.

 

[WaylonMercy5150]

Still not as embarrassing as rocking a Juggalo tattoo. And a misspelled one at that.

 

[SamSchmidt]

Wasn't ...coolio in that Wu-Tang fighting game? That game was the shit. I wish I could remember it

 

[Zer]

View attachment 534743

I loved this as a kid. Not sure how it holds up today its been awhile. I had a huge crush o the chick furthest to the right

Man, Michelle Pfieffer looks like a junkie frontman for a shitty indie band. To think back then she was one of the hottest women on the planet

dat catwoman doe

 

[Plissken]

If he shaved everything off he'd look like Uncle Coolio that works at the garage down the street.

 

[JabToucher]

I bet just because of that one song there's tonnes of eighteen year old flange who'd jump on him. Just to say they did it with that "gangstas paradise" guy.

The harlots!

 

[Losfer Words]

He got wrekt on hot ones

 

[soggyfist]

Is that a tat on top of his head?

That little bit of fuzz was holding on for dear life.

 

[magicmarker]

He made it through another deer season as a solid 12-pointer. Props...

 

[clutchCAT420]

Way ahead of his time...

 

[KONG-D'SNT-TAP]

Come alongggg and ride on a fantastic voyage

 

[WaylonMercy5150]

Come alongggg and ride on a fantastic voyage

Have some of my malt liquor Mr. O

 

[Amerikuracana]

He pretended to be mad at weird al.. Like Amish paradise wasn't "cool."

He fails on every level.

 

[WaylonMercy5150]

He pretended to be mad at weird al.. Like Amish paradise wasn't "cool."

He fails on every level.

Story goes he was going to step to weird al at VMA's so Al wasn't going to do the braids. Other rappers went to Al and demanded he do the braids and if Coolio steps they will crush him. He never stepped.

 

[Amerikuracana]

Story goes he was going to step to weird al at VMA's so Al wasn't going to do the braids. Other rappers went to Al and demanded he do the braids and if Coolio steps they will crush him. He never stepped.

Thank you lol

 

[WaylonMercy5150]

Thank you lol

How much of a fucking cunt do you have to be to want to step to weird al?

 

[Amerikuracana]

How much of a fucking cunt do you have to be to want to step to weird al?

He should have just asked to be in the video with a big fake beard doing some Amish shit. Would have been cool.

 

[MadSquabbles500]

I think he trying to get the powers that be to make Dangerous Minds sequel because he bout to go broke.

 

[WaylonMercy5150]

He should have just asked to be in the video with a big fake beard doing some Amish shit. Would have been cool.

Probably wouldn't be rocking struggle braids right now if he made that choice.

 

[MadSquabbles500]

View attachment 534743

I loved this as a kid. Not sure how it holds up today its been awhile. I had a huge crush o the chick furthest to the right

View attachment 534747

mmmm, that early 90s style, and latino culture.