He originally got the name "Coolio" from his friends in Compton when he was younger, who compared his musical talent to that of Julio Iglesias but since he rapped instead of sang, and had a fresh cool mellow feel, he was given the name Coolio Iglesias.
Despite his much-troubled childhood, he learned how to read from the Pelton Power Program for Kids at age 12, founded by Texas jazz musician Aaron Pelton. He began performing after graduating high school. He was part of the hip-hop group WC and the Maad Circle, appearing on their 1991 debut Ain't a Damn Thang Changed, but he left shortly thereafter to pursue a solo career. After releasing one single, "Watcha Gonna Do", an addiction to crack cocaine derailed his career. After working as an airport security guard for a brief period, Coolio was able to kick his habit and then returned to performing and recorded his debut album. It Takes a Thief was released in 1994. The signature track was "Fantastic Voyage", which sampled the Lakeside song of the same name and became a massive nationwide hit.
In 1995, "Gangsta's Paradise", a track written to the tune of Stevie Wonder's "Pastime Paradise" from Songs in the Key of Life, was placed on the soundtrack to Dangerous Minds because executives at Tommy Boy Records felt it would not sell. It ended up being a Grammy-winning #1 pop hit in the US, and became the first rap single to sell over a million copies in the UK, while becoming the first gangsta-rap single to top the UK charts. The video, which featured Minds star Michelle Pfeiffer and was directed by Antoine Fuqua, received heavy airplay on MTV.
"Weird Al" Yankovic parodied the song with "Amish Paradise", from his 1996 album Bad Hair Day, which mocked the rapper's distinctive hairstyle on the cover as well. Coolio claimed that he was unaware that Weird Al's record label had gotten permission from Tommy Boy Records for Al to do a parody of the song. During his Grammy acceptance speech, Coolio made no secret of his discontent, which led to discord between the singer and the record company.
A series of photos taken at the XM Satellite Radio booth at the 2006 Consumer Electronics Show suggests that Al and Coolio may have made amends.
After his 1995 hit album Gangsta's Paradise, Coolio continued touring and started acting. He contributed another Lakeside-sampled single, It's All the Way Live (the band even appeared in the video), to the soundtrack of the 1996 Whoopi Goldberg film Eddie, which flopped in theaters. His third album, 1997's My Soul, sold poorly despite the success of the single C U When U Get There, whose melody lines are based on Pachelbel's Canon. It was featured on the soundtrack to the 1997 Martin Lawrence film Nothing To Lose, and landed Coolio a spot on The Tonight Show. After leaving Tommy Boy, he appeared in a few films and set up his own record label, Crowbar Records.