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In 1975, a not-well-known Willie Nelson performed on the pilot of the now-legendary TV show Austin City Limits.

Gov’t Mule played a three-hour halloween gig largely covering Pink Floyd at Boston’s Orpheum Theatre in 2008, which was released as Dark Side of the Mule six years later in 2014.

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We’re just two lost souls swimming in a fish bowl year after year – Pink Floyd “Wish You Were Here”, 1975
The Rolling Stones’ sax player Bobby Keys, Outlaw Country legend Waylon Jennings, and Rock & Roll originator Buddy Holly all lived in the same neighborhood in Lubbock, Texas & were friends before each was famous. Jennings & Keys both played with Holly’s backing band The Crickets (though Keys did after Holly’s death).
Someone told me there’s a girl out there with love in her eyes and flowers in her hair – Led Zeppelin, “Going to California”, 1971

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