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Bob Dylan wore a Triumph Motorcycle t-shirt on the cover of his iconic 1965 album ‘Highway 61 Revisited’, just over one year later, Dylan crashed his Triumph motorcycle, derailing his career.

Waylon Jennings started his musical touring career as one of Buddy Holly’s backing band, The Crickets.

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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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Majestic Records Gold Eagle Baseball T-Shirt
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