An early fan of the Kentucky native was actor Bill Murray, who showed to a tour stop in Charleston, South Carolina. "He's an enthusiastic music lover, so he really elevated the crowd," Stapleton told Rolling Stone Country. "He's a bit of a hype man. We hung out after the show, and it was very interesting."

Stapleton's former band, the SteelDrivers, actually appeared on the soundtrack to 2010's Get Low with Murray, but the conversation wasn't limited to their past on-screen time together.

"We went to the place next door and stayed till it closed," Stapleton recalled. "I was drinking bourbon, I think he was drinking wine. The conversation ran the gamut -- it was the kind of thing that could take a turn at any moment. He has a lot of interesting philosophies."

"If you can imagine a conversation with a compilation of all of those characters he's played -- from Caddyshack to Lost in Translation -- then you can imagine a conversation with him," he explains. "I wasn't gonna ask him for Caddyshack stories, though."