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The ‘Sleeping on the Blacktop’ singer-songwriter has always been outspoken against Music City's mainstream country scene.
The ‘I Wanna Love You Forever’ hitmaker released the second instalment of her ‘Nashville Canyon’ project last week.
Kraft is the CEO of the Patriots, with Chesney enjoying a longstanding affinity with the NFL team.
The ‘Tennessee Orange’ singer-songwriter also serenaded the crowd with a stellar rendition of ‘Six Months Later’.
The singer opened up about growing up with music, his granddad Buford’s influence and his Damn Country Music Tour on The Tonight Show.
Over the last 22 weeks, the track has danced around the top of the radio ranking.