5. Coolio
“Gangsta’s Paradise” rapper Coolio comes in at number five on our list. Since making his debut in 1994, Coolio’s braids seem to now be holding on for dear life. Whoever his stylist is really needs to inform the rapper that a bald head and braids just don’t look good together (and probably never will). Apparently, the ladies have never minded his crazy hairstyle because he has a total of ten children from four different relationships!
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