Coolio

In the mid-'90s, several actions were undeniably not cool in hip-hop: lifting obvious R&B samples for your hit singles; regular participation in MTV sporting events; calling yourself Coolio. Artis Leon Ivey Jr. committed all these sins, and had not only his biggest hit but his hairstyle parodied by Weird Al as punishment. And yet without Coolio's trailblazing efforts, Puffy might have never had the gumption to rip off Diana Ross, a reputed MC like Method Man would have never showed up on Rock n Jock to drop an easy pop fly, and Beavis would have had one less weird mantra to obsess over when he OD'd on sugar.

But though you made Coolio's acquaintance on the radio or MTV, don't go reaching for that greatest hits just yet, even if it is the only Coolio disc where you can find his fun contribution to the Nickelodeon network, "Aw Here It Goes (Theme From Kenan & Kel)." The original albums carefully place those party jams in a sometimes desperate urban context, most effectively on Gangsta's Paradise. Once the mood is set by the high gothic tone of the title track, LV's harrowed vocal straining for release as Coolio's slow burn sinks deeper into paranoia, the primarily upbeat remainder of the album sounds less like R&B frivolity and more like a collection of momentary escapes from despair. Coolio's sales slumped with My Soul, but his music remained consistent -- "C U When U Get There" is one of the few hip-hop elegies to rise above maudlin self-pity.

Coolio's visual legacy shouldn't be ignored, either -- and I'm not just talking about the hair. The videos for "Fantastic Voyage" and "1,2,3,4 (Sumpin' New)" document the downside of California dreamin' from a pedestrian's perspective. From Brian Wilson to Dr. Dre, after all, that West Coast fantasy has always rested on the mobility that comes from a sharp ride. But no matter how he got there, Coolio's parties always seemed worth the effort -- way more fun that those Snoop Dogg snoozers where everyone gets comatose on cheap weed and lounges around playing Gameboy while bored strippers give them head. (KEITH HARRIS)

From 2004's The New Rolling Stone Album Guide