“Covering the Hits” looks at covers of a randomly-selected #1 hit from the past sixty-odd years.

Christopher Cross’s soft rock classic “Sailing” isn’t quite what it seems to be on its shimmery surface. For one thing, though it was technically related to actual sojourns on the water Cross took in his younger days, it wasn’t strictly about sailing. Back in 1995, in the midst of a manic (understatement) interview on The Howard Stern Show, of all places, he broke it down.

Cross said his standard explanation of the song’s inspiration ’til then was that it was about the transportive power of art. The song’s most famous line,”the canvas can do miracles” referred not to a boat sail, but to an actual painting (I admit that for years I thought he meant a freakin’ sail, don’t tell anyone). But when he thought about it later, he realized it was about combination of escaping a stressful home situation (his father’s alcoholism and subsequent emotional distance) as well as his gratefulness to a particular friend who would take him out sailing and as a result became something of a surrogate dad to Cross.

And so “Sailing” is not just for sailors but is in fact for all of us wistful humans, eloquently expressing musical thanks to everyone’s blessed escape hatches and guardian angels. “Sailing” is in fact a state of mind. I spent a fair amount of time with this thing as well as the album it came from, titled, uh, Christopher Cross, in my sad teenage bedroom back in the day. so I was warmed to hear Cross’s latter-day analysis. And surely I’m not the only living being who has succumbed to its mellow, melancholic charm and still voluntarily listens to it on a semi-regular basis forty-odd years later (yeah, okay, work with me here people).
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