Booking Coolio

To book Coolio for your next event, please fill in the form to the right. One of our booking agents will reply within 24 hours.

The staff of Headline Booking Group will work with you to produce a memorable event. Get started now by filling out our no-obligation Artist Request Form and we will work with you to book Coolio or another artist for your event.




Coolio was one of the first rappers to balance pop accessibility with gritty, street-level subject matter and language. Yet despite his nods to hardcore, his music was clearly more happy-go-lucky at heart.

After high school he began taking his high school interest in rap to the stage and took his performing name from a dozen contests in which someone called him ‘Coolio Iglesias.’ He became a regular on Los Angeles rap radio station KDAY and cut one of the earlier SoCal rap singles, ‘Watcha Gonna Do.’


Coolio cut another single and wound up landing a deal with Tommy Boy. Accompanied by DJ Brian ‘Wino’ Dobbs, Coolio recorded his debut album, It Takes a Thief, which was released in 1994. The lead single, ‘County Line,’ was a humorous recounting of the indignities of welfare, but the record really took off when ‘Fantastic Voyage,’ a rap remake of the funk classic by Lakeside, was released as a single. Accompanied by a typically playful video, ‘Fantastic Voyage’ rocketed to number three on the pop charts, pushing It Takes a Thief into the Top Ten and past the platinum sales mark.

Following up his breakthrough success, Coolio teamed up with gospel-trained singer L.V. on a tune based on Stevie Wonder’s Songs in the Key of Life cut ‘Pastime Paradise.’ ‘Gangsta’s Paradise’ was a social statement about ghetto life, and the music was dark, haunting, and spellbindingly atmospheric, placing it on the soundtrack to the film Dangerous Minds, which starred Michelle Pfeiffer as a tough inner-city teacher. Released as a single, ‘Gangsta’s Paradise’ was a staggeringly huge hit; it became Coolio’s first number one pop single and also the first ghetto-centric rap song to hit number one in the U.K. Its chart longevity was such that, even with the Mariah Carey/Boyz II Men duet ‘One Sweet Day’ setting a new record for most weeks at number one that year, ‘Gangsta’s Paradise’ still managed to beat it out as the number one single of 1995. It later 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 in 1996, and the safe-sex anthem ‘Too Hot’ was fairly popular as well. Meanwhile, Coolio toured the world, contributed the theme song to the Nickelodeon comedy series Kenan and Kel, and began pursuing an acting career, making his screen debut with a cameo in the 1996 comedy Phat Beach; he would also land a small role in the following year’s Batman and Robin.

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