We’re partial to songs that can really put us in a different mental space than where we actually are. When the weather is rough, songwriters who write about sailing can transport us out on the water in an instant.
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These four songs take different approaches to the topic. And, in one case, the word “sailor” is used in a somewhat sarcastic fashion in a song about heartbreak. Nonetheless, we’d set a course for these tracks any day.
“Sail On, Sailor” by The Beach Boys
The Beach Boys were in a state of chaos when they recorded the album Holland, released in 1973. They recorded the bulk of the album in the titular location. Longtime member Bruce Johnston had quit the group at that stage, and Brian Wilson wasn’t involved much at all. Meanwhile, new members Blondie Chaplin and Ricky Fataar joined up for the record. “Sail On Sailor” speaks to some of the wildness of the project. Five writers are credited on the track, including Brian Wilson and his old Smile buddy Van Dyke Parks. Nonetheless, the song is a charmer right from the opening moments. Much of that can be credited to Chaplin, who gives a standout performance on lead vocals.
“Come Sail Away” by Styx
Styx had made quite a large leap from relative obscurity to a solid touring outfit by the mid-70s. But they were still a bit shy of the top tier of rock bands, at least from a commercial standpoint, when they released their 1977 album The Grand Illusion. That’s partly why “Come Sail Away” comes draped in aspirational lyrics. Keyboardist Dennis DeYoung, who wrote the song and sings lead on it, wanted his group to make that next step. Those desires bled into the words to the song. The interesting part of “Come Sail Away” is that the quiet piano opening certainly sounds like we’re out on the waters. But the thrilling synthesizer section and some of the later lyrics suggest we’re sailing to the Milky Way here.
“Sailing” by Christopher Cross
Let’s just stop for a second to appreciate what Christopher Cross pulled off with his self-titled album in 1979. The guy managed a sweep of the Big 4 Grammy Awards. And “Sailing”, which went to No. 1 on the pop charts, provided the impetus for a lot of that success. That’s a lot of accomplishments for a song that mostly sings the praises of a restful day out on the waters. Cross was recalling sailing trips that he took as a teenager, trips that took him away from the tumult in his life at the time. The timing of the song certainly helped, as it landed right in the midst of the soft-rock boom. But Cross also deserves credit for understanding that there was something to be said for the restrained approach to writing, singing, and recording.
“O Sailor” by Fiona Apple
This is the one song on this list that holds only a tangential relationship to sailing as an activity (although the video makes the connection). The consensus is that much of the material on Fiona Apple’s 2005 album Extraordinary Machine emanated from her breakup with filmmaker Paul Thomas Anderson. “O Sailor” is one of the songs on the record that certainly seems aimed at an ex. The narrator explains how her own reticence to move forward in a relationship paid off in this case, as some of her worst fears were realized. Still, she expresses disappointment about how things transpired. The use of “Sailor” plays up that angle. She thought she had someone who would join her on life’s voyage, only to be disabused of that notion.
Photo by Michael Ochs Archives/Getty Images
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