• This is a reworking of Stevie Wonder's 1976 song "Pastime Paradise." It wasn't Coolio's idea to use Wonder's song; a singer named Larry Sanders - who goes by the stage name L.V. (Large Variety) - started working on it and sent a demo to Collio, who was looking for a song to record for the 1995 movie Dangerous Minds. Starring Michelle Pfeiffer, the film is about a troubled school and the challenges faced by the students and the idealistic teacher played by Pfeiffer. Coolio wrote a lyric to express the feelings of despair and abandonment felt by the kids at the school, putting it to the track Sanders created. Along with the song's producer David Rasheed, Coolio and Sanders crafted the song, with Sanders singing the hook. They still had to clear the sample from Stevie Wonder, and this proved difficult, as he rejected the first version of "Gangsta's Paradise" because it contained swearing. After Coolio rewrote the lyric, Wonder gave his approval.
• Having grown up in Compton, California, Coolio could certainly relate to the gangsta lifestyle (so could the song's co-writer Larry Sanders, who survived a shooting), but he says that the song is not about him, but about the kids portrayed in Dangerous Minds who feel they don't have control of their lives.
• This won the Grammy in 1995 for Best Rap Solo Performance.
• Coolio's first hit came a year earlier with "Fantastic Voyage," a party jam that made #3 in the US. His record company, MCA, was hoping he would stay in that groove and release more upbeat songs - when they heard the brooding "Gangsta's Paradise" they were afraid it would alienate his fans.
• Weird Al Yankovic recorded a popular parody of this called "Amish Paradise." Coolio did not give him permission to use it and claimed Al "desecrated" his song. They eventually made peace and appeared together at the 1996 American Music Awards.
• Weird Al wasn't the only one to parody the song: "Shepherd's Paradise" is the parody version performed by ApologetiX, while "Algore Paradise" is a parody by Paul Shanklin satirizing Al Gore and Bill Clinton.
• The first line of this song comes from the bible, Psalm 23:4: "Yea, though I walk through the valley of the shadow of death, I will fear no evil: for thou art with me." While King David praises God's protection like a shepherd to his flock, Coolio realizes that he walks alone in his valley - a volatile "gangsta's paradise."
• Joined by the New York Boys Choir, Stevie Wonder performed this song with Coolio and L.V. at the 1995 Billboard Music Awards, where it won for Single Of The Year. A new arrangement was need to extend the song so Wonder would have room to sing, so Coolio joined Stevie at his studio to work it up before the performance. Wonder came on stage about halfway through the song to a rousing ovation. Later in the performance, he sang the "living in a gangsta's paradise" line while L.V. acknowledged the original by singing "living in a pastime paradise."
• For 22 years, this held the record for the longest running #1 single in Australia since the first ever ARIA Chart was listed on July 10, 1983. It sat on the throne for 13 weeks, beating the likes of Eminem's "Lose Yourself," which stayed at the summit for 12 weeks. Coolio's tune was eventually usurped by Ed Sheeran's "Shape Of You," which spent 15 consecutive weeks atop the listing in 2017.
• This was the first hard-core rap song to hit #1 in the UK. It was also the best selling rap single in the UK until Puff Daddy's "I'll Be Missing You" displaced it two years later.
• Fourteen years after this song first appeared on the UK charts, it returned to the British Top 40 as a result of Coolio featuring in the 2009 series of Celebrity Big Brother.

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