Kenny Chesney plays on a June night during this year’s Trip Around the Sun tour, which grossed nearly $115 million. (Jill Trunnell)

Mark Donovan panicked.

Country superstar Kenny Chesney, as usual, was playing before a packed stadium. On this particular night, about 12 years ago, it was Lincoln Financial Field, home of the Philadelphia Eagles. Midway through the show, Chesney ran to the side of the stage to grab Donovan, a senior executive with...

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