Then: If you were a rapper in the early Nineties and wanted to make a big splash, it was a good idea to get a crazy haircut. Coolio went for the I-Just-Stuck-My-Finger-Into-An-Electrical-Outlet look when he dropped his breakthrough single "Fantastic Voyage" in 1994. The G-funk song became an enormous hit, but the follow-up – unfortunately titled "Mama I'm in Love Wit' a Gangsta" – didn't go anywhere, and it seemed like Coolio would go the way of Nate Dogg. But the following year, Coolio's "Gangsta's Paradise" was featured on the soundtrack to the Michelle Pfieffer-starring film Dangerous Minds. The song became one of the biggest hits of 1995 and was absolutely inescapable. Even people that didn't listen to much rap knew every single word. Coolio's hits continued for a few more years, but he's been largely off the charts since "C U When You Get There" dropped in 1997.
Now: Coolio's music career may be on the rocks, but he's been smart about staying in the spotlight. It seems like there's not a single reality show he's unwilling to appear on, and in 2008 he even tried to pull an Osbournes with the short-lived Coolio's Rules. That didn't work out, but he's been happy to appear on Celebrity Big Brother in England or Rachel vs. Guy: Celebrity Cook-Off here in America. If there's a camera, Coolio is there.