Coolio

Even though his greatest hit had the word "gangsta" in the title, Coolio wasn't really a gangsta rapper. Instead he was the accessible face of West Coast rap, a street-tough yet positive personality with a sense of humor and a social conscience, and a reassuring figure in the era of N.W.A. and 2 Live Crew. Like N.W.A., Coolio (born Artis Leon Ivey, Jr, and taking his name from a spin on Julio Iglesias) came straight outta Compton. He attended college and worked as a security guard, and did fall briefly into the gang lifestyle as a teen: He ran with the Crips but never became a member; he was briefly addicted to crack and served jail time for cashing a stolen money order.

After the regional success of his first single "Watcha Gonna Do" he entered rehab and stayed straight thereafter, but his second single "You're Gonna Miss Me" didn't catch on. His debut album for Tommy Boy, It Takes a Thief was his breakthrough, drawing lyrically from the shadier parts of his past in a humorous, generally nonviolent way. The single "Fantastic Voyage," based on the Lakeside hit of the same name, was a smash, hitting Number Three in the Billboard hot 100. And it didn't hurt that the tune had a clever beach-party-themed video while MTV was still friendly to rap.

The next single "Gangsta's Paradise" again threw a socially aware spin on gangsta themes, and again drew from a familiar song (in this case, Stevie Wonder's "Pastime Paradise"). It was an even bigger hit, making Number One, and earning the honor of a Weird Al Yankovic parody ("Amish Paradise"). During 1995-96 Coolio was everywhere, scoring two soundtrack hits ("It's All the Way I Live (Now)" from "Eddie" (1995) and "Hit 'em High" from "Space Jam" (1996)) and collaborating with everyone from his former group WC and the Maad Circle to old-school funkers Kool & the Gang (whose singer JT Taylor sang on the Coolio hit "Too Hot").

He even did a theme for the hit series "Kenan & Kel" (Nickelodeon (1996-2000). This however was the peak of Coolio's fame. His third album My Soul yielded another hit with "CU When I Get There" (also based on an earlier hit-in this case a much earlier one, Pachelbel's "Canon in D"), but sales dropped off after that. 2006's Return of the Gangsta was only a modest hit despite a Snoop Dogg guest shot, and he stopped releasing albums after 2009's unsuccessful From the Bottom 2 the Top.

He did however become a fixture on TV playing on his '90s celebrity, appearing on "Celebrity Wife Swap" (ABC 2012-15) and "Celebrity Cook-Off" (Food 2012-14). Coolio briefly made headlines after an arrest in September 2016: While travelling to Dallas to guest at a Vanilla Ice show, he was arrested at LAX for possessing a stolen gun, which was found when his carry-on bag was screened. Though he faced a three-year sentence, he got off with probation and community service. Coolio died on September 28, 2022 at the age of 59.