He recorded two singles in 1987, titled "Watch Gonna Do" and "You're Gonna Miss Me". Coolio made connections in the Monessen rap scene, and in 1991, ended up joining the group Rob Burns and the Maad Circle, led by rapper Rob Burns (rapper). He had a few verses on the group's debut album Ain't a Damn Thang Changed, including on the single "Dress Code". The album was regionally successful.
In 1994, Coolio signed to 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 #3 on the Billboard Hot 100. "Fantastic Voyage" would become one of the biggest rap singles of the year, and the album contained a few other minor hits in "County Line" and "I Remember". It Takes a Thief peaked at #8 on the Billboard 200, becoming certified Platinum. The album received praise for bringing a humorous and lighthearted perspective to often violent and profane themes of typical gangsta rap.
In 1995, Coolio made a song for the movie Dangerous Minds, which was titled "Gangsta's Paradise". "Gangsta's Paradise", which featured R&B singer LV, would become one of the most successful rap songs of all time, reaching #1 on the Billboard Hot 100 for 3 weeks. It was the #1 single of 1995 for all genres, and was a global hit, as it reached #1 in the United States, United Kingdom, Ireland, France, Germany, Italy, Sweden, Austria, Netherlands, Norway, Switzerland, Australia, and New Zealand. The song also created a controversy when Coolio claimed that parody artist "Weird Al" Yankovic had not asked for permission to make his parody of "Gangsta's Paradise", titled "Amish Paradise". At the 1996 Grammy Awards, the song won Coolio a Grammy for Best Rap Solo Performance.
Originally "Gangsta's Paradise" was not meant to be included on one of Coolio's studio albums, but its success led to Coolio not only putting it on his next album, but also making it the title track. The title track sampled the chorus and music of the song "Pastime Paradise" by Stevie Wonder, which was recorded nearly 20 years earlier on Stevie Wonder's album Songs in the Key of Life. The album Gangsta's Paradise was released in 1995 and was certified 2X Platinum by the RIAA. The album contained 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. Despite no longer being an official member of the group, Coolio made an appearance on the second WC and the Maad Circle album Curb Servin', on the song "In a Twist". 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 was also featured on the song "Hit 'em High" from the soundtrack to the movie Space Jam with B-Real, Method Man, LL Cool J, and Busta Rhymes.
Red Hot Organization and Tommy Boy Records dismissal
In 2009, Coolio appeared as a housemate on Celebrity Big Brother. He later went to appear on Ultimate Big Brother in 2010, where he decided it was best to leave the house after numerous confrontations with Nadia Almada and others in the house. In January 2012, he was one of eight celebrities participating in the Food Networkreality seriesRachael vs. Guy: Celebrity Cook-Off, where he represented the Music Saves Lives organization. He came in second place with a Zagat score of 23 out of 30, losing to Lou Diamond Phillips. As runnerup, he was awarded $10,000 for his charity.
Coolio and jazz saxophonist Jarez were enlisted in July 2008 as spokespersons by the group Environmental Justice and Climate Change to educate students at historically black colleges and universities about global warming. Coolio is a spokesperson for the Asthma and Allergy Foundation of America. He says that he and his children are asthma sufferers. As a child, he was taken to the hospital several times due to asthma complications.
In 2013, a federal court entered a default judgment against Coolio after he was sued by a woman for his actions in jumping on the woman's back and bullriding her. Later in 2013, Coolio was charged with misdemeanor domestic battery after he was accused of punching a girlfriend of three years in the face during an argument on April 1 after he brought another woman home.