1963 - Born on August 1st in Los Angeles, California. Coolio was one of the first rappers to balance pop accessibility with gritty, street-level subject matter and language.
1980 - At 17, he spent several months in jail for larceny (apparently after trying to cash a money order that had actually been stolen by one of his friends).
1991 - He began making connections in the L.A. hip-hop scene, meeting up with WC and the Maad Circle and guesting on their debut album, Ain't a Damn Thang Changed.
1994 - Accompanied by DJ Brian "Wino" Dobbs, Coolio recorded his debut album, It Takes a Thief, which was released.
1996 - Won a Grammy for Best Solo Rap Performance.
- The triple-platinum Gangsta's Paradise album kept the hits coming: the bright party anthem "1, 2, 3, 4 (Sumpin' New)" hit the Top Ten, and the safe-sex anthem "Too Hot" was fairly popular as well.
1997 - Coolio and seven members of his entourage were arrested for allegedly shoplifting from a German clothing store and assaulting the owner; he was later convicted on accessory charges and fined on November 22nd.
1998 - He was convicted for unlawful possession of firearms on September 15th.
1999 - He played triplets in the film Tyrone, but had to postpone a Crowbar promotional tour after an auto accident. He continued to take a number of small film roles, but his much-delayed fourth album remained only a rumor (though it was confirmed that he had recorded "The Hustler," a rap update of Kenny Rogers' "The Gambler" with Rogers himself on vocals).
2003 - Was featured in a subplot of Daredevil, but his scenes were eventually deleted. However, he still appears in the film's trailers. His scenes were restored in the Director's Cut DVD.