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The Monkees may have started out as a pre-packaged pop band in the mid-'60s, relying on session players and pro songwriters, but they gradually took more control of their music. By 1969, when the group appeared on The Johnny Cash Show, the country legend's short-lived variety program, they'd evolved considerably—now contributing to their own writing and playing some of their own backing tracks. But getting a co-sign from Cash was no small feat, proving just how far they'd come.

And they probably didn't hurt their case by leaning into the folkier side of their sound. Even decades later, it's a trip seeing these guys share the stage with acoustic guitars in hand. Cash was right there to open the seven-minute segment, grinning widely as he strummed and belted the opening bars of the band's debut single, "Last Train to Clarksville." He chuckled his way through some comedic bits with his guests (Davy Jones, Michael Nesmith, Micky Dolenz), who halted the performance with the signature wacky energy that propelled their self-titled TV series.