The Late Coolio And Kenny Rogers Were Friends And Collaborated On A Song Together

Although many different genres of music are branches with very similar roots, the mashup of a prolific country artist and trailblazing rapper might seem hard to imagine. But that’s exactly the team that Country Music Hall of Fame inductee Kenny Rogers and Grammy Award winner Coolio created with their surprising friendship and unexpected collaboration.

Coolio, born as Artis Leon Ivey Jr., died on Wednesday, September 28, at the age of just 59. During his career, he achieved mainstream success for himself thanks to albums like Gangsta’s Paradise and My Soul, and solidified hip-hop’s own popularity on the airwaves. But perhaps most unique was his work with and inspired by Rogers, which resulted in “The Hustler.”

Two music giants, Coolio and Kenny Rogers, became friends and worked together

The year was 1978 and Rogers released his signature song, which became his treasured persona, “The Gambler.” The Library of Congress has immortalized the song in the National Recording Registry as a mark of its importance. It has a good beat and life lessons are delivered in a smooth manner, all according to Rogers’ personal creed to treat his fans to a degree of positivity. Along the way of his own musical journey, he ended up crossing paths and working with Coolio, who would have listeners bopping their heads to hits like “Fantastic Voyage” in the ’90s.

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“I enjoy working with people that you wouldn’t expect me to be with,” Rogers revealed in an interview with MTV. “It’s a great opportunity for me to get kinda involved in another form of music.” But his readiness to work with Coolio came from another place as well: “As a friend of Coolio, I’ll do whatever he wants me to do.” This resulted in an update to “The Gambler.”

The Gambler meets The Hustler through Kenny Rogers and Coolio

The final product was 1998’s “The Hustler,” a modern retelling of “The Gambler” for a new time and setting. “The agreement we had is that the message had to be a positive message,” Rogers outlined of his work with Coolio. “Because I don’t wanna hurt myself and the people who follow me, and I don’t wanna hurt him, with the people who follow him.”

“The Hustler” then was given the spirit of “The Gambler,” this time with elements of the ’90s aboard that train bound for nowhere. But it hearkens to its muse in an even more direct way, by having Rogers himself singing between Coolio, delivering famous lines from “The Gambler.” This is just one of the songs by Coolio that make up his legacy that is now being celebrated and mourned following his passing. Give a listen to this unique collaboration between Coolio and Kenny Rogers below.