11/11/2008 AT 04:30 PM EST
The CMA Awards aren't until Wednesday, but Kenny Chesney
is already ready to knock fans' cowboy boots off.
As preparation for his upcoming performance
, the singer played a impromptu gig with legendary reggae band The Wailers at Tootsie Orchid Lounge in Nashville Monday night.
Word of the "commando show" had leaked to fans, who flooded the club to watch the award-winning singer run through nearly four hours of his own hits and reggae favorites that The Wailers helped popularize with Bob Marley. At one point, Chesney's friend Kid Rock even joined in for a few songs.
"You know, this is by far the coolest performance I've ever had on an awards show, and to be able to take it to the streets, to let the fans get to experience this with me, this might be one of the best nights of my life," Chesney told the crowd.
Chesney's biggest problem now may be trying to match Monday night's show when he's at the CMA Awards.
"We could hear [fans] making their way down the street on our bus after, and it was awesome," Chesney said. "You know, hardcore country fans singing 'One Love.' Now that's what I call making music universal."
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