Outlaw Country Cruise 2020: 10 Best Things We Saw

After midnight, the Norwegian Pearl’s casino becomes the epicenter of the boat, with artists and cruisers mingling, gambling, and drinking. And the late-night DJ sets provide the ideal soundtrack. This year’s stop in Falmouth, Jamaica, allowed guest DJ Jesse Malin to lean hard into a theme of reggae and punk, a combo that was all but perfected by the Clash. Shooter Jennings, meanwhile, dug into an eclectic, inspired mix of country and experimental music, making the case that the Grammy-winning producer’s natural state may be in front of the laptop.

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