What do you do with a drunken sailor?
You put him in a longboat 'til he's sober. Duh. You won't find that song on my boating playlist because it reminds me of standing in the back of my middle school choir and silently mouthing "watermelon pits" because I didn't know the words to whatever song we were supposed to be singing that day. But what you will find on my playlist is 16 jams guaranteed to rock the boat.
- Pearl Jam – "Drifting": It's hard to believe but the grunge gods from Seattle are now officially classified as classic rock. This is the rare song in their catalog that is mellow but not desperately depressing.
- The Beach Boys - "Sloop John B.": The best song on this list. Mmmmm, maybe.
- Lyle Lovett – "If I Had a Boat": For some reason if Lyle Lovett had a boat he'd ride a pony on it. No one really knows why, and I've found it's best not to dwell on these things. But whatever, the guy bagged Julia Roberts, he must be doing something right.
- Styx - "I'm Sailing Away": Tell me about it bro, I want to sail away too sometimes.
- Bob Dylan and Eric Clapton – "The Water is Wide": Dylan and Clapton could sing the phone book and I'd listen to them.
- Crosby, Stills and Nash – "Southern Cross": My buddy Slash swears up and down no woman can resist this song. It's his go-to. Like if it wasn't for this song he might be 30 years old still wondering what it feels like to kiss a girl.
- Jimmy Buffett – "Boats, Beaches, Bars and Ballads": What you really thought Buffet wasn't going to make an appearance? Pfft.
- Harry Belafonte – "The Banana Boat Song": Isn't it bad luck to load crates of bananas onto a boat? (Shrug). Good song either way.
- Billy Joel – "The Downeaster Alexa" You'd think writing songs this sad would drive a man to drink. Oh wait.
- Gordon Lightfoot – "The Wreck of the Edmund Fitzgerald": Gordon Lightfoot loves him some boat music. Believe that.
- The Lemonheads – "Rudderless": Something tells me this song isn't about boats. Whatever, Lemonheads, you put the word "rudder" in a song this good it's making my boat playlist 8 days a week. Deal with it.
- Otis Redding – "Sittin’ on the Dock of the Bay": Not even joking I CRUSH this song in karaoke, even the whistle solo. Especially the whistle solo.
- Cat Stevens – "Longer Boats": Before Cat Stevens lost his mind and got all terrorist-y, he used to sing a pretty good tune.
- Split Enz – "Six Months in Leaky Boat": Dude fix your boat, it's sinking.
- The Waterboys – "Fisherman’s Blues": Great song, no idea what it's about, still though, good one.
- Jimmy Buffett – "A Pirate Looks at 40": What? Jimmy Buffet ain't no one-hit wonder! Can't hold that guy down. We're talkin' 'bout boat songs here, hows Buffett not gonna make that list twice?