Country artists didn't used to sing about sailing and wiling away their time on big boats and being pirates bound for tropical paradises very often -- perhaps because, once upon a time, their audiences couldn't afford such a life of leisure -- but they sure do now. Or at least Kenny Chesney does, with weekend seafarers like Little Big Town, Zac Brown and Craig Morgan (the economically confusing "Redneck Yacht Club") chiming in now and then. Back in the day, the boat-song task was, unsurprisingly, more the province of yacht-rockers like Christopher Cross and Blues Image, with The Beach Boys occasionally trading in surfboards for more opulent vessels. And of course parrot papa Jimmy Buffett -- who until the mid-'80s had more success on the pop chart than the country chart -- logged more nautical miles than anybody.
So for your oceangoing pleasure, here's a mix that pulls together some old rock and newer country sailors devoted to this manly pursuit: "Manly" because, as Looking Glass and Buffett himself make clear in "Brandy" and "Fins," respectively, the only women in most of these songs are ones being circled by shark-like drunken seamen in dockside taverns. Or as Jay Ferguson puts it in "Shakedown Cruise": "The captain laughs, he says, 'You boys want some sex? You can squeeze the sails, you can lick the decks.'" And then there's the aptly named The Lonely Island (rappers, sort of, but what the heck), navigating their "big blue watery road" and telling Poseidon what they did with some mermaid. Probably it was really just a manatee, but that's no reason to abandon ship. As one great mariner said, "If the wind is right you can sail away and find serenity."