In 1980, Christopher Cross was a newcomer enjoying the kind of debut most musicians could only dream about when an unlikely single took him all the way to the top.
“Sailing” hit No. 1 on the Billboard Hot 100 during the week of Aug. 24, 1980, spending one week at the summit. It became Cross’ first No. 1 hit after his debut single, “Ride Like the Wind,” featuring Michael McDonald on backing vocals, had peaked at No. 2 earlier that year. Cross would eventually score a second No. 1 with 1981’s “Arthur’s Theme (Best That You Can Do).”
But “Sailing” didn’t just rule the charts 46 years ago. Decades later, it received an honor that seems almost tailor-made for the song.
In 2007, VH1 named “Sailing” the No. 1 song on its list of the 40 Most Softsational Soft-Rock Songs, placing it ahead of Styx’s “Babe,” Rupert Holmes’ “Escape (The Piña Colada Song),” Barry Manilow’s “Mandy” and Chicago’s “If You Leave Me Now.” “Sailing” was also named to Amazon Music’s 100 Greatest Soft Rock Songs of All Time playlist.
The distinction is particularly fitting now that “Sailing” is widely regarded as one of the defining examples of yacht rock, though Cross himself has said he and his contemporaries originally knew the style by a different name.
“We both have become part of that ‘West Coast’ sound, now known as Yacht Rock,” Cross wrote in 2013 for HuffPost while discussing Hall & Oates and the genre’s unexpected resurgence. He added that yacht rock had become “such a cult fascination” around the world.
Perhaps the most remarkable part of “Sailing’s” journey to No. 1 is that it wasn’t necessarily supposed to make that journey at all.
Cross’ self-titled debut album had already produced “Ride Like the Wind,” which spent four weeks at No. 2. According to music historian Fred Bronson’s “The Billboard Book of Number One Hits,” the label initially favored “I Really Don’t Know Anymore” as the follow-up.
But there was a complication. Like “Ride Like the Wind,” the song featured McDonald on backing vocals, and Cross’ management was concerned about depending on two consecutive singles featuring the Doobie Brothers singer.
So another song was selected: “Sailing.” It proved to be quite a second choice.
“Sailing” went to No. 1, and Cross later acknowledged during his Grammy acceptance speech that the song was his favorite on the album and hadn’t originally been intended as a single.
The recording itself also contained a happy accident. Cross has recalled that the song’s orchestral opening resulted from the wrong button being pushed during recording. It had been intended to begin with the acoustic guitar before the accidental opening became part of the finished record.
“Sailing” was technologically unusual for 1980, too. Recorded using the 3M Digital Recording System, it became one of the first digitally recorded songs to make the charts.
The technology behind “Sailing” may have been cutting-edge, but the inspiration for it went back to Cross’ adolescence.
Cross has said the song was inspired by an older high school friend named Al Glasscock, who would take him sailing when Cross was a teenager. Glasscock became something of a surrogate older brother during an emotionally difficult period in Cross’ life, and their trips gave the future singer a way to escape the pressures he was experiencing.
The two eventually lost touch, but nearly three decades later, The Howard Stern Show reunited them in 1995. Cross confirmed that those long-ago sailing trips had inspired the song and later sent Glasscock a copy of his platinum record.
Related: The Greatest Guitar Solo You Can’t Hear Is Hidden in a 1980 Classic
By the time Cross was writing songs of his own, he’d already spent years performing. He began on drums as a seventh grader, later switched his focus to guitar and eventually played in bands around Texas before Warner Bros. signed Cross as a solo artist.
If reaching No. 1 was the high point of “Sailing’s” summer, what happened several months later turned Cross’ debut into music history.
The scale of Cross’ overnight success was so extraordinary that it nearly became the story itself. “The Rolling Stone Encyclopedia of Rock & Roll” noted that the five Grammys Cross won for his debut ultimately attracted more attention than the music that earned them, an unusual predicament for an artist who had seemingly arrived fully formed.
At the 1981 Grammy Awards, Cross became the first artist ever to sweep all four General Field categories in a single night: Album of the Year for Christopher Cross, Record of the Year and Song of the Year for “Sailing,” and Best New Artist. “Sailing” also won Best Arrangement Accompanying Vocalist(s), giving Cross five Grammys that night.
No artist managed the same four-category sweep again for 39 years, until Billie Eilish accomplished it at the 2020 Grammys.
Cross’ debut ultimately produced four Top 20 hits: “Ride Like the Wind,” “Sailing,” “Never Be the Same” and “Say You’ll Be Mine.” The album went on to be certified five-times platinum in the United States.
The sudden success wasn’t something Cross took for granted. Speaking about his career at the time, he reflected on how quickly everything had changed.
“When I’m old I’d like to be able to say all this happened because my music was good,” Cross said in Bronson’s book.
Forty-six years after “Sailing” reached No. 1, the song’s journey hasn’t ended. It has gone from an unlikely single to a chart-topper, a three-time Grammy winner and, eventually, VH1’s pick for the No. 1 soft rock song of all time.
For a song about getting away from it all on the water, “Sailing” has traveled remarkably far.
Related: 1980 Olivia Newton-John Hit, Written for a Box Office Bomb, Became a Four-Week No. 1
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