This tranquil classic evokes sailing on the open sea, leaving any troubles on the shore. In a Songfacts interview with Christopher Cross, he told the story of the song:
"I was just at home sitting in this cheap apartment, sitting at the table. I remember coming up with the verse and chorus, and the lyrics to the first verse of the chorus all came out. These tunings, like Joni [Mitchell] used to say, they get you in this sort of trance, so all that came out at once: 'It's not far down to paradise...' The chorus just sort of came out.
So I got up and wandered around the apartment just thinking, 'Wow, that's pretty f--kin' great.' I just thought, 'That's really cool.' So then I sat down and had to try to come up with other stuff to make the rest of the song, but I thought I had something there.
Then it took about two years before I had a bridge to that song, because the modality of the modal tuning thing, it gets pretty linear, and you've got to be careful. There are writers - I won't mention who - whose songs can get kind of boring because everything's this modality. So I knew I needed to lift the song out of that modality in the bridge and make key changes.
It took about two years before I came up with the bridge that changes all the keys to where it lifts, but it was a pretty special moment."
Cross wrote this song about his memories sailing every summer with a friend in Texas. It became the paragon of "Yacht Rock," a term used to define a form of easy listening music favored by the rich. And what defines yacht music better than a song about sailing?
Eventually, Yacht Rock caught on with the proletariat, and even spawned a cover band, the Yacht Rock Revue, made up of seven members who do it as a full-time job. "Sailing" is pretty much their "Free Bird," and it has a powerful impact on the crowd. "That song is exceptionally smooth," Nicholas Niespodziani of the band told Songfacts. "Everything we do is pretty smooth, but then there's like, a next level of smooth, that's just so vibed out. A lot of times, you can create excitement by being not excited, and that song is the perfect example of that: It's so chilled out that it gets people pretty amped up."
On the Howard Stern radio show, Cross explained that sailing with his friend got him away from the trials and tribulations of being a teenager. Cross said that if the guy had taken him bowling and he enjoyed it, the song could have become "Bowling."
Michael Omartian, who was Cross' producer, also contributed keyboards and background vocals to the album. Omartian has worked on many hit songs - he co-wrote "She Works Hard For The Money" and produced "We Are The World" with Quincy Jones. Jay Graydon, who is also a hit songwriter and producer, played guitar on the Christopher Cross album. He singles out Omartian and David Foster as guys who are great to have in sessions. "These guys are just incredible musicians," he told Songfacts. "I'm pretty good at doing string stuff and synth overdubs, and of course guitar overdubs and stuff, but you bring good guys in, then it gets really masterful."
Christopher Cross won three Grammy Awards for this song: Record of the Year, Song of the Year, and Best Arrangement Accompanying Vocalist. The following year he won an Oscar for Best Song with his "Arthur's Theme (Best That You Can Do)" from the Dudley Moore movie Arthur. His second album Another Page was released in 1983. That album contained "Think Of Laura," which was his last Top 40 hit.
This was Christopher Cross' second single, following his #2 charting "Ride Like The Wind." Cross considers "Sailing" a "complete" song and one of the best he's written, but he never thought it would be a hit. "I thought the song was way too introspective," he said in his Songfacts interview.
It was anything but smooth sailing for Cross in 2020 after he became one of the first celebrities to get coronavirus, which he picked up in Mexico after performing in Mexico City on March 7, shortly before North America went into lockdown. Cross revealed his diagnosis on April 3, calling it "the worst illness I have ever had." In October, he said he contracted a rare neurological disorder called Guillain-Barre Syndrome, which affects his speech, memory, and movement, likely as a result of the virus.