Coolio's first major record deal, in 1989, was with Columbia Records. However, Coolio decided he wanted to start a label of his own, and refused to make his contract with Columbia Records official, and Columbia decided not to renew his contract. His first official record deal after leaving Columbia was with Tommy Boy Records, where he recorded two albums with a budget of $250,000. The second album, Don't Sweat the Technique, was released in 1993. Coolio's second contract was with Tommy Boy, which lasted through 1997. His third official contract was with Sony/Arista Records, where he released the albums WC & The Maad Circle and Curb Servin', in 1995 and 1996 respectively. Coolio's next contract was with Carson/Lilacs Records, where he released the album Freaky Tales in 1997.
He also released More Than Coolio (1996) and Album II: The Gift of Coolio (1997), a collection of his greatest hits. The latter of the two was his last album to receive a Gold certification from the Recording Industry Association of America (RIAA). The More Than Coolio album was certified Platinum by the RIAA for selling 500,000 copies in the United States.
In 1994, Coolio debuted his own production company, Coolio Music. In 1996, he also launched his Cool World clothing line with merchandise that he said would be the first to have a green certification to conform with his environmental beliefs. The line was later picked up by companies like Nike, Adidas and Reebok. In addition, Coolio made a cameo appearance on The Sisterhood of the Traveling Pants as a talking poster, similar to the poster featured on the first season DVD special features of the program.
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