Toby Keith – Sailboat for Sale

Toby Keith, the country music king of red Solo cups and summertime anthems, takes a humorous yet relatable turn with “Sailboat for Sale”. This track, found on his 2015 album “35 MPH Town”, tells the tale of a sailor stuck in a frustrating situation, all wrapped up in a catchy, toe-tapping melody.

“Sailboat for Sale” is a story song filled with Keith’s signature wit. The narrator, a self-proclaimed “drunken sailor,” finds himself stuck with a sailboat he clearly despises. The lyrics paint a picture of a frustrating purchase, perhaps fueled by rum-induced spontaneity (“An old pirate sold me on it / G / D / We traded straight across / The boat I thought I wanted / A / For the boat I hate”).

The song’s humor lies in the sailor’s predicament. He’s stuck with a vessel that doesn’t suit his fancy, one that seemingly lacks the necessary “throttle” for a real sailing adventure. “Sailboat for Sale” becomes a lament for a bad deal, with the catchy chorus (“Sailboat for sale / With a drink in my hand and a sailboat for sale”) serving as a hilarious plea to anyone willing to take this unwanted vessel off his hands.

But beneath the surface of the song’s humor lies a relatable theme. We’ve all, at some point, made impulsive purchases that turned out to be less than ideal. “Sailboat for Sale” taps into that feeling of buyer’s remorse, delivered with a healthy dose of self-deprecating humor.

While the song doesn’t delve into the specifics of the “ocean” the sailor can’t seem to reach, it evokes a sense of yearning for something more. Perhaps it’s the open seas and the thrill of adventure, or maybe it’s simply a desire for something different from the monotony of his current situation.

“Sailboat for Sale” is a lighthearted and entertaining song that showcases Toby Keith’s ability to weave humor and relatable themes into a catchy country tune. It’s a perfect addition to any playlist that needs a dose of laughter and a reminder that even the toughest cowboys can make bad decisions sometimes.