Sep 242021

“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).

Sean Duncan – Sailing (Christopher Cross cover)

In terms of covers, the overwhelming approach to “Sailing” has been smooth and faithful. When I say smooth, I mean smooth jazz. After listening to what felt like hundreds of covers, it started to feel as if every recording session of an intrepid interpreter started with the declaration, “Oh you call that ‘on hold’ music? I’ll show you what an ‘on hold’ song sounds like, mofo.” It was rare for anyone to color outside the lines… which is supremely disappointing because “Sailing” is a ginormous and open-hearted soft rock bull with undeniably strong melodic bones. You can push “Sailing” around and it will still remain upright, the song can take it, we all can.

With that, meet singer-songwriter-multi-band member Sean Duncan. His 2016 cover is a devil, full of riff-age and volume. Built on a bedrock of power drums (baby), proggy synth, and sporadically chugging guitar, Duncan turns the song into a gloriously sloppy stadium anthem. If you want to bang your head, this is the “Sailing” for you.

Rumer – Sailing (Christopher Cross cover)

It was back in 2010 that British singer-songwriter Rumer exploded politely onto the scene with her still-sublime debut album Seasons Of My Soul. Since then she has released another album of originals and three cover albums, as well as a handful of EPs. She has proven herself to be a masterful interpreter with exceptional and downright eclectic taste, covering tunes by cult heroes like Jimmy Webb, Townes Van Zandt, and Tim Hardin to name a (very cool) few. Within that, she’s also proven to be a dab hand at ’70s-’80s AM radio pop (her cover of “Sara Smile” is honey on top of honey).

Case in point: her take on “Sailing,” as featured on her B Sides and Rarities collection. A delicate piano line leads the way and is quickly complimented by a swath of lush strings and seductively fulsome drums, the latter bringing to mind Russ Kunkel’s classic brushes on “Fire And Rain.” Then there’s Rumer’s vocal, which is of course simultaneously beautiful and handsome. This is the “Sailing” to listen to while actually sailing.

P.J. Pacifico – Sailing (Christopher Cross cover)

P.J. Pacifico’s 2012 cover of “Sailing” has something most of the existing versions don’t, namely a thumbs up from Christopher Cross himself. In an interview with Songfacts in 2013, Cross said he thought Pacifico’s take was “very cool” adding “it’s kind of different, and somebody who interprets it differently is more interesting to me.”

And it is different. Pacifico flips the commonly employed smooth jazz vibe on its ass and instead shapes “Sailing” into a shuffling windblown pop song that lands somewhere between Duncan Sheik and America (think “Ventura Highway” or “Sister Golden Hair”). It is also blessed with a video so true to the song’s wistful-wishful sentiments that it is practically a documentary. It is the anthesis of glossy neon glamour, with nary a sailboat or ocean in sight. All we see is lonely P.J. existing, breathing, commuting, communing with aquatic nature under overcast skies. Use this “Sailing” to soundtrack solo city wanderings as you embrace your inner sad sack and descend to paradise.

Lesley Gore – Sailing (Christopher Cross cover)

If you only know Lesley Gore from her still-perfect anthem of joyful despair “It’s My Party” (more on that here) or classic defiant declaration “You Don’t Own Me,” then this cover may come as a surprise. Gore’s version of “Sailing” was the centerpiece of her 1982 album The Canvas Can Do Miracles which is, yup, named for the song’s seminal signature line. It hews so close to the original in terms of production and overall sound that you might think what’s the point…until Gore starts singing, that is. Her vocal performance is exquisite. Subtle, convincing and unspeakably warm. That is the point. This is your “Sailing” for staring out rain-speckled windows.

Ely Bruna – Sailing (Christopher Cross cover)

There are roughly ten trillion smooth jazz style covers of “Sailing,” and most are pretty interchangeable. But amongst the multitudes, singer Ely Bruna’s 2015 take is a standout. It is basically a celebration of the song, as opposed to a sensitive interpretation of its sentiment. This thing is positively exuberant. Bruna and her band scrub away the songs innate somberness and kick up the tempo, swathing it in lush harmony as well as some exceptionally ostentatious “sexy” clarinet. The arrangement is pretty imaginative, with enough space for Bruna to do some pretty sweet belting as the song progresses. And the overall sound is very reminiscent of groovy underrated retro popsters Swing Out Sister (always a good thing). There’s some groovy ad-libbing in the chorus, a nice high note in the coda, and a corny but sincere Cross namecheck at the end.

It took a few listens for this one to sink in, but there’s no question it’s got that wonderfully ineffable something. Meet the “Sailing” for cruising down the highway and leaving your troubles behind.

Bonus Cut: I know what you’re thinking. Why didn’t she mention Yacht Rock??? Isn’t “Sailing” the genre’s definitive theme song??? Okay, here’s the deal, and apologies in advance because I’m about to have a personal, wtf, get off my lawn moment.

Yacht Rock is a made-up genre (circa 2005) that subjectively corrals songs and artists from the actual genres of Soft Rock and West Coast (aka the smooth pop sounds that were filling the Top 40 and Adult Contemporary charts from roughly 1975-1984). It was created primarily for comedic purposes and is always spoken of with irony, all of its subjects served up and meant to be enjoyed as “guilty pleasures.”

Anyway, I have some issues with both Yacht Rock and “guilty pleasures.” I’m not crazy about about the judgmental underbelly living in each thing, the suggestion that you can only like certain songs or artists ironically, that some aren’t worthy of full-blown unabashed out in the open love. Also, a lot of the songs categorized as Yacht Rock were favorites of mine as a young one, and I feel irrationally protective of them (or rather, how seriously I took them as a kid).

Not too long ago I did what nerds do in these situations and wrote angsty breakdowns (mental and information-wise), about both the Yacht (read here) and the guilt (read here). Please come spit in the wind with me (and, added bonus, read about one of the finest, most rockin’, for arguments sake, “Yacht Rock” albums ever).

“Just a dream and the wind to carry me and soon I will be free….”

Cover Me is now on Patreon! If you love cover songs, we hope you will consider supporting us there with a small monthly subscription. There are a bunch of exclusive perks only for patrons: playlists, newsletters, downloads, discussions, polls - hell, tell us what song you would like to hear covered and we will make it happen. Learn more at Patreon.

  2 Responses to “Covering The Hits: “Sailing” (Christopher Cross)”

Comments (2)
  1. Yay, go, Hope!! Love your impassioned rant, which I heartily endorse. The songs? Less so, but hey.

 Leave a Reply

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <s> <strike> <strong>