In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
A couple of months ago, Billie Eilish swept the Grammys, winning all four of the major cross-category awards: Album, Record, and Song Of The Year, as well as Best New Artist. Those of us who are paid to figure these things out quickly noticed that Eilish was only the second person ever to accomplish this feat. The first was Christopher Cross, and he’d done it 39 years earlier. (Cross was nice about the whole thing.)
The Grammys are a famously meaningless awards show, but they’re instructive in a very particular way: They show the record business the way the record business wants to be seen. The industry functionaries who vote for Grammys tend to believe that they’re putting forward the best that their world has to offer. In 2020, the music business wants to be seen as sharp and adaptive, so they select a teenage-polyglot streaming star — someone who scans as fashionable and idiosyncratic, who records in her bedroom and dresses like a SoundCloud rapper — as their standard-bearer. In 1981, an extremely different record industry went with a very different face: A babyfaced Texan who made pop records so smooth that they seemed to dissolve into the air.
Christopher Cross came from San Antonio, and he spent years toiling on that city’s club circuit, playing in a blues-rock cover band. He was apparently friendly with people like ZZ Top and Stevie Ray Vaughan, and he tells a story that he once played with Deep Purple, filling in for Ritchie Blackmore at a San Antonio show when Blackmore was too sick to play. Cross was already in his late twenties when he signed to Warner Bros. When he released his self-titled 1979 debut album, he told Rolling Stone that he wasn’t into rock music anymore, that he was happy with just being a purely commercial pop act.
Warner signed Cross because an A&R guy had liked his voice, and the original plan was for him to record songs from other songwriters. But Warner paired Cross with Michael Omartian, the successful pop-insider producer who’d helped mastermind the 1976 #1 “Theme From S.W.A.T.” and who’d produced #1 hits for Andy Kim and Alan O’Day. Omartian liked the songs that Cross had written, and he helped convince higher-ups that Cross should record his own stuff. Omartian came from California’s soft-rock scene, and he’d done session-musician work for people like Steely Dan and Loggins & Messina. He brought in some big names to sing backup on Cross’ debut album: Don Henley, JD Souther, Nicolette Larson. Omartian also brought in Doobie Brothers leader and future solo star Michael McDonald to sing backup on a couple of songs, and that made a huge difference.
McDonald lent his unmistakable yarl to Cross’ debut single “Ride Like The Wind,” a slick and enjoyably preposterous outlaw jam that became an out-of-nowhere smash, peaking at #2 in the spring of 1980. (It’s a 7.) Warner wanted to release “I Don’t Really Know Anymore,” a song with even-more-prominent Michael McDonald backup vocals, as the follow-up single, but McDonald’s management objected. So instead, Warner released “Sailing,” a blissed-out ballad that appeared late on the album. Cross himself thought the song had no shot at becoming a hit. Today, it’s his signature song.
Cross has said that he thought “Sailing” was too introspective a song to make an impact. But “Sailing” really isn’t that introspective. It’s a literal surface-level song. On it, Cross sings about being on a boat and feeling good about it. That’s it. The boat doesn’t represent anything. We never get a weird last-minute twist like the one on Styx’s 1977 banger “Come Sail Away,” where aliens invite the narrator onto their starship at the end of the song. (“Come Sail Away” peaked at #8; it’s a 10.) Instead, Cross just has a nice time sailing: “Well, it’s not far down to paradise/ At least, it’s not for me/ And if the wind is right you can sail away/ And find tranquility.”
Cross spent a couple of years writing “Sailing.” He came up with the opening verse one day at his apartment, but he couldn’t figure out the right chord changes for the bridge until some time later. For those of us who are too musically stupid to recognize these things, though, “Sailing” keeps the same general vibe throughout its runtime. It’s an extremely chill record, an expensive flutter that works hard to evoke the “all caught up in the reverie” feeling that Cross describes.
“Sailing” basically works against everything I tend to value in music. There’s very little forward motion to the song. It’s not fast or hard or exciting. It’s not heavy or emotionally intense or revealing, either. There’s no rhythmic play, no syncopation. “Sailing” is about finding a peaceful state of mind and then trying to extend that feeling for as long as possible. These things have made “Sailing” a favorite of the pseudo-ironists who make up the yacht-rock crowd, the half-joking scene that finds something reassuring in the no-ripples slickness of a very particular era of popular music. I’ve got no time for any of that shit. “Sailing” is a much more sincere song than anything Steely Dan would ever record, but it’s right in that same zone of shit that I hate.
And yet “Sailing,” on its own terms, is an effective piece of work. It has a certain glossy power. Cross and Omartian recorded the song digitally, back when most people didn’t do that, and it certainly sounds like the kind of thing that could only come out of a sterile and airlocked studio. Everything sounds rich and clean: The softly burbling guitar, the insistent triangle dings and conga bloops, the restrained hum of the strings. Cross sings in a pinched tenor, and he never seems to be pushing himself too hard, even when he hits the chorus. Instead, he sounds like he’s just murmuring to himself — as if he’s attempting to deal with the stress in his life by conjuring the serenity that he experienced that day on that sailboat.
As a piece of music, “Sailing” is so lush and buttery that it’s practically ambient. For my own baked-in you-can’t-mosh-to-it reasons, I’m naturally biased against a song like “Sailing.” And yet I can’t fully deny its comforts. It’s a song so tied to its moment that it’s practically nostalgic for itself, and there’s a hint of sadness in its overwhelming chill. It’s made with craft. I respect craft.
In the immediate aftermath of Billie Eilish’s big Grammy night, Christopher Cross looks something like a cautionary tale: An anointed superstar who couldn’t make good on his early push and who quickly fell away into obscurity. But Cross stuck around for at least a little while after “Sailing.” He’ll be in this column again.
BONUS BEATS: Here’s Kool Keith singing a few bars of “Sailing” on the 1996 Dr. Octagon track “Blue Flowers Revisited”:
BONUS BONUS BEATS: Here’s the cover of “Sailing” that *NSYNC included on their self-titled 1997 debut album:
*NSYNC performed “Sailing” with Christopher Cross at something called the Blockbuster Entertainment Awards in 1999. Brian McKnight introduced Cross as “Chris Cross,” which is funny, and the members of *NSYNC all flew above the audience like Peter Pan while Cross remained onstage. I like to imagine the conversation where the producers had to decide whether to make Cross fly, too. Anyway, here’s that performance:
(*NSYNC will eventually appear in this column.)
BONUS BONUS BONUS BEATS: Puff Daddy rapped over a “Sailing” sample on “Best Friend,” a Mario Winans collab that peaked at #59 in 2000. Here’s the video:
(Puffy Daddy will eventually appear in this column.)
BONUS BONUS BONUS BONUS BEATS: Here’s Krayzie Bone rapping over a “Sailing” sample on the 2006 track “Paradise”:
(Krayzie Bone will eventually appear in this column, both as a guest-rapper and as a member of Bone Thugs-N-Harmony.)