While Kris Kristofferson was a struggling songwriter, he worked as a custodian at Columbia Studios in Nashville when Bob Dylan recorded Blonde on Blonde (they didn’t meet). Just seven years later, Kristofferson co-starred with Dylan in the 1973 film Pat Garrett and Billy the Kid.

Folk music legend John Prine was working as a mailman until he was discovered by film critic Roger Ebert, who wandered into a bar Prine was playing and wrote a glowing review in the Chicago Tribune.

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