In the late 1980s and early 1990s, Coolio seemed to be living in the shadows. A product of Southern California, the MC born Artis Leon Ivey, Jr. made some of his first noise alongside WC, DJ Crazy Toones and the collective known as WC & The Maad Circle.

As the group recorded their sophomore album, 1995’s Curb Servin’, Coolio stepped out of Dub’s perceived shadow and inked a solo deal with Tommy Boy Records. There, 1994’s debut It Takes A Thief surprised anybody and everybody. With limited support, and no ties to established West Coast mainstream guard (Death Row, Ruthless), Coolio made a platinum album. Huge on sampling, and utilizing scaled back PG-13 lyrics in the “Ain’t No Fun” era, Coolio became the other SoCal MC with elaborate braids, memorable wardrobe, lowriders in his video, and a true showmanship for the MTV camera. “Fantastic Voyage” literally brought Lakeside back to the charts with it, as Coolio’s imagery of moving from the trunk to the sunshine seemingly symbolized his career surge. A Top 10 album, Coolio suddenly joined Naughty By Nature as a flagship label act, and one of Hip-Hop’s crossover sensations. Even for Snoop (who shouted out Coolio on “Doggy Dogg World”), the rapper was not perceived as a gimmick, but as a low-profile MC with dues paid.

For his 1995 follow-up, Coolio aimed to make a statement. It Takes A Thief reached the mainstream as a street-certified party album. Gangsta’s Paradise aimed for substance. Moreover, as was popular at the time, Coolio attached his product to a soundtrack. The Michelle Pfeiffer-starring Dangerous Minds film was among a growing movie trend highlighting difficult classrooms, and teachers shutting down the nonsense.

The resulting song used Coolio’s skill-set. On August 8, 1995, Coolio released “Gangsta’s Paradise” (months before the album of the same name would follow). The MC was able to capture a grim reality, without being particularly graphic or profane. Instead, teaming with South Central Cartel’s L.V., Coolio made a grandiose record about an attitude that people either related to, or wanted to better understand.

In a Rolling Stone retrospective, Coolio, L.V., and producer Doug Rasheed recall the Grammy Award-winning hit 20 years later. L.V. reveals that the song was presented to South Central Cartel, whose member Prodeje suggested Coolio. Upon hearing the beat, Coolio freestyled the famed opening bars to the song. “You know, I like to believe that it was divine intervention. ‘Gangsta’s Paradise’ wanted to be born; it wanted to come to life, and it chose me as the vessel,” he explains today. It is added that Tommy Boy’s unnamed A&R at the time, thought it would be “a good album cut.” The label brass would take the finished song and initially try to license it to Bad Boys soundtrack. After that offer was bested, the team sold the film rights track to Disney/MCA Records for a reported $100,000. Additionally, Coolio’s original lyrics were too harsh (including allusions to sodomy), holding back Stevie Wonder from clearing the “Pastime Paradise” sample. Coolio made the requested changes, before Antoine Fuqua (Training Day, Southpaw) shot the music video (which Michelle Pfeiffer starred in, 12 years after Scarface).

“Gangsta’s Paradise” represents a pinnacle in Coolio’s career. The MC would return for WC & The Maad Circle’s sophomore album that same year. He would grab a Grammy, a multi-platinum album of the same name (and anchor a multi-platinum soundtrack). 1997’s My Soul would keep Coolio in the mainstream conversation, and charts-and-plaques pageantry. However, the early collaborator to E-40, Ras Kass and J-Ro would fade from the spotlight by the end of the 1990s. Hardly a one-hit wonder, Coolio seemingly is emblematic of a transitional time in Hip-Hop. Like 50 Cent or Eminem, he is a testament to patience and persistence. Like MC Hammer, Sir Mix-A-Lot, or Young MC, he may have been too popular for his own endurance later on. However, the numbers and history prove that Coolio is not a one-hit wonder. His greatest contribution, from a national scale, remains relevant in its sound and messaging 20 years later.

Read: Rolling Stone‘s Oral History of “Gangstas Paradise” by Coolio & L.V.

 Related: WC Explains Why He Avoided The Westside Connection & Cypress Hill Beef (Video)