Coolio recorded his first single in 1987, titled “Whatcha Gonna Do?”.^[1] In 1988, he recorded “What Makes You Dance (Force Groove)” with Nu-Skool. Coolio made connections in the L.A. rap scene, and in 1991, joined the group WC and the Maad Circle, led by rapper WC. He is a credited co-contributor on the group’s debut album Ain’t a Damn Thang Changed, including on the single “Dress Code”.^[12]

In 1994, Coolio signed a recording contract with Tommy Boy Records and released his debut solo album It Takes a Thief. The lead single “Fantastic Voyage” received heavy rotation on MTV and peaked at No. 3 on the Billboard Hot 100, becoming one of the biggest rap singles of the year. Other minor hits from the album include “County Line” and “I Remember”. It Takes a Thief peaked at No. 8 on the Billboard 200,^[13] becoming certified Platinum.^[14] The album received praise for bringing a humorous and lighthearted perspective to the often violent and profane themes of typical gangsta rap.^[10]

In 1995, for the film Dangerous Minds, Coolio released “Gangsta’s Paradise“, featuring R&B singer L.V.. It became one of the most successful rap songs of all time, topping the Billboard Hot 100 for three weeks. It was the No. 1 single of 1995 in the United States for all genres and was a global hit topping the United Kingdom, Ireland, France, Germany, Italy, Sweden, Austria, Netherlands, Norway, Switzerland, Australia, and New Zealand charts. “Gangsta’s Paradise” was the second-best-selling single of 1995 in the U.K. The song also created a controversy when Coolio claimed that comedy musician “Weird Al” Yankovic had not asked for permission to make his parody of “Gangsta’s Paradise”, titled “Amish Paradise“.^[15] At the 1996 Grammy Awards, the song won Coolio a Grammy Award for Best Rap Solo Performance.^[16]

Originally “Gangsta’s Paradise” was not meant to be included in one of Coolio’s studio albums, but due to its success, Coolio included it on the album, making it the title track. It interpolates the chorus and music of the song “Pastime Paradise” by Stevie Wonder, which was recorded nearly 20 years earlier on Wonder’s album Songs in the Key of Life. The album Gangsta’s Paradise was released in 1995 and was certified two-times Platinum by the RIAA, selling more than two million copies in the US alone.^[17]

The album contains two other major hits in “1, 2, 3, 4 (Sumpin’ New)” and “Too Hot” with J. T. Taylor of Kool & the Gang doing the chorus.^[18] Despite no longer being an official member of the group, Coolio appears on the second WC and the Maad Circle album Curb Servin’ on the song “In a Twist”.^[19] In 1996, Coolio had another top 40 hit with the song “It’s All the Way Live (Now)” from the soundtrack to the movie Eddie. He is also featured on the song “Hit ’em High” from the soundtrack to the 1996 film Space Jam with B-Real, Method Man, LL Cool J, and Busta Rhymes.^[20]

In 2014, the band Falling in Reverse did a cover of “Gangsta’s Paradise” for Punk Goes 90s Vol. 2, with Coolio making a cameo in the music video.^[21]

In 1996, Coolio appeared on the Red Hot Organization‘s compilation CD America Is Dying Slowly, alongside Biz Markie, Wu-Tang Clan, and Fat Joe, among many other prominent hip-hop artists. The CD meant to raise awareness of the AIDS epidemic among African-American men.^[22] That same year, he recorded the music video “Aw, Here It Goes!” for the opening sequence of the Nickelodeon television series Kenan & Kel, which ran for four seasons.^[23]

Coolio’s third solo album, My Soul, came out in 1997. Although it contains the major hit “C U When U Get There” and the album went platinum, it failed to reach the success of his previous two albums. Coolio was subsequently dropped from the Tommy Boy Records label. Since then, 2001’s Coolio.com, 2003’s El Cool Magnifico, 2006’s The Return of the Gangsta, and 2008’s Steal Hear, 2009’s From the Bottom 2 the Top, and 2017’s Long Live the Thief have not charted on any Billboard chart. He did have a minor hit in the UK in 2006 with “Gangsta Walk” (featuring Snoop Dogg).^[24]

While touring with hip-hop duo Insane Clown Posse, Coolio received a tattoo as a homage to the group’s fanbase, reading “Jugalo Cool” [sic]. He stated that the misspelling was intentional. Coolio performed at the Gathering of the Juggalos.^[25]

Coolio is featured on an international collaboration track called “Fuck the DJ” by UK rapper Blacklisted MC, also featuring Bizarre of D12, Adil Omar (from Pakistan), and Uzimon (from Bermuda). The song premiered on music website Noisey from Vice in October 2014.^[26]