Remember When: Dave Chappelle Joined Forces With John Mayer & Questlove for the Most Unlikely Waylon Jennings Cover Ever

Performing for over 50 years, Waylon Jennings helped push the outlaw movement in country music into the mainstream. Releasing hit songs like “I’ve Always Been Crazy”, “Riders in the Sky”, and “Highwayman”, the country singer collaborated with stars like Willie Nelson, Jessi Colter, and even Johnny Cash. Landing a spot in the Country Music Hall of Fame, the singer passed away back in 2002. But while gone, Jennings’ music continues to inspire as comedian Dave Chappelle once performed his famous song “Theme from The Dukes of Hazzard (Good Ol’ Boys)”. 

Videos by American Songwriter

Over the last year, country music has seen a drastic shift as singers like Post Malone and Beyonce showed interest in the genre. For Beyonce, she broke into the genre thanks to her popular album Cowboy Carter. And for Malone, fans anxiously await his country album to drop. But for Chappelle, he isn’t looking for a career in music as he covered the iconic theme song. It seemed the comedian wanted nothing more than to have a little fun with Questlove and John Mayer.

[RELATED: 3 Songs You Didn’t Know Featured Dave Chappelle]

Fans Can’t Get Enough Of Dave Chappelle Singing

Always willing to share his thoughts on current events and the state of the world, Chappelle’s cover of the iconic song was part of a skit for his famous Chappelle Show. And fans seemed to love the video as comments included, “I loved that Dave Chappelle brought us all together by pointing out all of our stereotypes and making us laugh at ourselves TOGETHER.” Another person added, “Imagine you’re walking in the early 2000’s down the road and you see John Mayer playing the electronic guitar with Dave Chappelle.” And one person insisted, “To this day Dave and John are still best of friends, John even showed up to Dave’s 50th Birthday show at Madison Square Garden and shared Jokes just like this skit!”

As for Jennings, songwriter Lee Thomas Miller once discussed the legacy that surrounded the country icon and how many didn’t know the man behind the mic. “Waylon’s kind of a mystery. I don’t think people really know how dark he was and just how intense he was. I mean, he was so politically incorrect, and he lashed out at the [Country Music Association (CMA)]. But I feel like culturally, Waylon and Willie [Nelson] are almost mythical, Marvel characters…”

(Photo by Charley Gallay/Getty Images for AT&T and DIRECTV )

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