Roy Orbison was the only singer who could make Johnny Cash grin like a schoolboy, and you need to hear these two legendary voices together on their 1969 live duet on “Oh, Pretty Woman”

Johnny Cash knew a legend when he saw one. That much was clear when Roy Orbison stopped by Johnny’s TV show in 1969. The pair sang Roy’s timeless hit “Oh, Pretty Woman” together, and joining his voice with the Texas crooner made The Man in Black smile from ear to ear. It was super heartwarming how much joy it gave Johnny to sing with Roy. Needless to say, hearing those two genre-defining voices together was heaven for fans.

Their voices both have so much character, and it’s fascinating to hear them sing in harmony together. You can’t help but smile watching the moment they share here. The little jokes Johnny adds here and there create such a fun and playful vibe, and Roy is loving it. They are two such titans of their genres, but here they are just two fellas having a ball jamming together. The Music Man has to say we are sure glad that Roy’s team shared this on YouTube for everyone to enjoy all these years later!

When Roy Orbison uploaded his duet with Johnny on YouTube, it hit three million views. Viewers loved to hear the throwback collab and added comments such as “Orbison must have had the best male voice ever recorded. I love seeing Johnny Cash totally enjoying Roy’s voice, almost in awe, but definitely holding his own” and “Johnny Cash seemed like such a good guy. No ego here. He let Roy do his thing and just tried to fit in. Great moment.”

Another classic performance from Roy that can be found on YouTube is “Go! Go! Go! (Down the Line)”. This was issued for the 30th anniversary of his live album Black and White Night Live. Roy’s band for the show featured a star-studded lineup that included Elvis Costello and Bruce Springsteen, both of whom drop solos in the song. Roy played the show on September 30, 1987. He’s in fine form here, and it’s hard to believe that he would die from a heart attack just a little over a year later on December 6, 1988.

Roy Orbison released “Oh, Pretty Woman” in August 1964 as a standalone single. The Texan hitmaker wrote the song with Bill Dees. The single hit number one on both sides of the pond. It subsequently placed at number four and seven on the year-end charts of the US and UK, respectively. The Music Man readers may recall that “Oh, Pretty Woman” has since become Roy’s signature song and a firm fan favorite. It is currently his most-streamed song on Spotify, with 845 million streams.

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