What rappers had the weirdest careers?

Mike Wins

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There's a couple that stand out to me

Slick Rick. Got to be one of the top 5 or 10 most influential hip hop artists. His whole style from the way he tell stories, the flow and English accent, to the image and fashion still among the most unique ever. Career got derailed by the prison sentence, but he did make a successful comeback in 1999. Then never dropped another album. Supposedly he the most sampled rapper of all time, and been sampled on some of the biggest hits of the last 30 years or so. And still got his publishing. So maybe he decided to go out on a good note and live off the royalty checks. But Rick still float on guest spots to this day and his style is timeless, it's crazy he never released an album in this century.

Mase. Dude was a superstar out the gate. He went the most commercial route possible but he could really rap his ass off when he wanted. Could thrive in any lane. Most effortless charisma of any rapper in the wake of Pac and BIG passing. Floor for his career should have been Ludacris run in the 00s. But his second album was dead on arrival with the unexpected retirement and he just disappeared.

Heard everything from getting caught doing some :dame: activities in a Range Rover, to getting run out of NY by some street dudes. But he went to Atlanta so the :dame: aspect should not have been an issue and there's plenty studios down there. He came back and had a couple hits with that clean album, then dipped out again. With nothing since but a couple aborted comebacks. This probably the winner for me.
 

Awesome Wells

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QTip!!!!!

Mos Def!!!

Both of these dudes constantly piss me off, with their careers.

Mos just sits around all day and does nothing. This bum should've been Top 10 by now.

giphy.gif
 

Mike Wins

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Both of these dudes constantly piss me off, with their careers.

Mos just sits around all day and does nothing. This bum should've been Top 10 by now.

giphy.gif

Where Mos get the money to retire at 40 like that? :heh:

I got it when he was gonna be an actor but he don't do that either
 

Awesome Wells

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Where Mos get the money to retire at 40 like that? :heh:

I got it when he was gonna be an actor but he don't do that either

He barely had a crib. LOL!! Dude was living in Africa and on couches for years.

Dodging the child support cases and all that. He said he didn't have any bread.
 
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