Billie Eilish and the Cautionary Tale of Christopher Cross

Meta: Billie Eilish’s Grammy sweep rewards a fresh voice in the pop music landscape, but did the Academy do her a disservice? Christopher Cross would like a word. 

What does a Grammy Award mean? What do four Grammy Awards mean? To the artist, that little gold gramophone represents the blood and sweat of artistic creation. In that respect, the value of the award comes without comprehensible value. No one succeeds in this business because they woke up one morning and, on a lark, decided to record hit track. That might be the spark, but that’s not “success.”

In the days and weeks surrounding the Grammy Awards, the industry elevates the nominees and ultimate winners above all others. They’ve been singled out among their peers. The Recording Academy has passed judgment. The winners get their nom de guerre etched in granite and a boost in recognition and sales.

This year, as you might have heard, Billie Eilish became the first woman to take all four major Grammy categories – New Artist, Record, Album, and Song – and the second artist to achieve that elusive clean sweep.

In one night, the industry crowned the now and future queen of popular music. Can you name the other artist to achieve the sweep? His name, now obviously synonymous with “the King of Rock and Roll,” is… Christopher Cross.

Christopher’s Cross To Bear

Christopher Cross became the surprise winner of the Big Four at the 1981 Grammy Awards. The newcomer went up against heavyweights Frank Sinatra and Barbara Streisand in Album and Record of the Year. Cross, then 29, a craftsman of middle-of-the-road contemporary “pop ‘n’ roll,” a style of music later christened “Yacht Rock,” shocked pundits and even his own record label. Warner Bros. didn’t even plan a post-Grammy party, as would be customary for a label with lofty award expectations.

Cross’ self-titled debut album produced four top 20 hits on the Billboard Hot 100. “Sailing,” the song for which he’s best known, reached #1. Four gramophones later, expectations for the artist reached a crescendo, but fate conspired against him.

After writing the Academy Award-winning theme for Arthur (“Arthur’s Theme”) with Burt Bacharach, Carole Bayer Sager, and Peter Allen, the inevitable backlash arrived. His second LP, Another Page, peaked at 11 on the Billboard 200, whereas his debut had lingered in the Top 10 for months. None of his subsequent records sniffed the Top 100. Cross’s career stalled a hot minute after launch when MTV hit airwaves on August 1, 1981. The doughy, soft-spoken vocalist didn’t stand a chance at stardom in a new pop-culture landscape driven by youth, image, and appearance. MTV immediately downgraded the importance of music in evaluating an artist’s cultural relevance. Hindsight also reveals the permanent folly of his Best New Artist victory over the heavily favored future Rock and Roll Hall of Fame inductees The Pretenders. The Recording Academy has a poor track record of evaluating new talent, so it’s always a questionable outcome when all the major awards fall into the lap of a new artist — even when that artist may have been as deserving as Christopher Cross in 1981… or Billie Eilish in 2020.

As much as things change, the more they stay the same-ish.

Billie Eilish Pirate Baird O’Connell connects with a teenage fanbase that sees her as more “real” than other stars, like Taylor Swift or Katy Perry or any of the other hundreds of carefully curated public personas. They see her as a rule-breaker and an anti-pop trendsetter. She speaks to the insecurities of their high-school entropy in many of the same ways that the grunge movement of the 1990s (and the punk scene before that) struck a rebellious nerve.

“I have taken out my Invisalign and this is the album,” she says after an unbecoming slurp on the prelude to her Grammy-winning debut album When We All Fall Sleep, Where Do We Go? It doesn’t get more real for a teenager than the sound of someone suffering through the weapons of orthodontia. There’s no arguing that she’s given pop-stardom a new dynamic. The teenager comfortable being herself. The teenage fashion-icon that fancies lime green hair, crafts patchwork skater-chic from mismatched thrift and glam and still lives with her parents. This is real — but this also demonstrates the continued importance of youth, image, and appearance. 

In a recent Vogue article, Eilish says, “That’s great, if I can make someone feel more free to do what they actually want to do instead of what they are expected to do. But for me, I never realized I was expected to do anything. I guess that’s what is actually going on—that I never knew there was a thing I had to follow.” This is healthy. This is a perspective that kids absolutely need to counterbalance the false perfection peddled on social media. She’s also used her Instagram fame and international stardom to marshal teenage voter registration and raise interest for environmental activism rather than as a showcase for #JustWokeUp pics. 

She’s the first artist born in the 21st century to hit #1 on the Billboard Hot 100 and the first teenager to record a James Bond theme for the upcoming No Time to Die. (Doesn’t this gig eerily echo Christopher Cross’ post-Grammy foray into soundtrack music with “Arthur’s Theme”? Cue her 2021 Academy Award.) Isn’t she also, at the moment, still just another zeitgeisty pop phenomenon until proven otherwise? How difficult must it be for a teenage singer/songwriter to hone her craft while hanging onto the side of a runaway train? 

Backlash, Expectation and the Future

Billie Eilish peddles the gothic and macabre through her videos filled with black tears and spider snacks, but she also giggles and hums and most importantly, experiments. When We Fall Asleep is immersive and remarkably focused, but it’s intermittently raw and doesn’t stray as far from traditional bubblegum sensibilities as most of her fans believe. It’s more a score for a scrapbook made up of darkside Lana Del Rey doodles and Billie’s favorite TV shows (The Office and Sherlock) than a sincere reflection of teenage angst. She’s crafting fictions (genuine fictions, but fictions nonetheless) and playacting like any other teenager forced to inhabit a place of expertise before she’s really lived. Teenagers look to her as a mental health icon. Her ability to be a functional, individualistic teenager while sharing deep, dark thoughts through her music inspires self-worth. 

One could easily argue that Lorde’s 2017 Melodrama (released when she was 21, but reflective on similar adolescent themes) succeeded as a more fully formed example of teenage introspection. Specific celebration of one album does not require the denigration of another and both can be enjoyed for exactly what they are. Billie Eilish has more unrealized potential, and this first homespun DIY avant-pop album marks the coming of a refreshing new perspective in mainstream music, but it might also be a disservice to elevate this particular offering to the rare echelon of supposed perfection. Anointing her with a Grammy sweep doesn’t do her any more favors than it did Christopher Cross 39 years ago.

Objectively, When We Fall Asleep features a number of creative choices that don’t quite pay off. The pitchy vocals and ukulele on “8,” for example, should never have survived the demo stage. I would never fault a good sample, but “my strange addiction” would have been better off without the jokey and conspicuous clips from The Office. Compare these two minor production foibles with the oversized confidence of a banger like “you should see me in a crown.” Her image, appearance, and justifiably devoted fanbase perhaps supplied fuel for the Academy’s valuation. 

The connection between Eilish and Cross might only be a coincidence, but it might be more. It would be a shame if Billie Eilish’s career turns out to be nothing more than another example of some destined-to-be-forgotten music of our moment. (Though we’re all pretty sure that Lil Nas X has that niche covered.) A teenage girl rebelling against conventions and striking a chord with a population that’s been lacking a voice. She’s not someone poised to fade away, and we should all feel a vested interest in her continued success – but it’s just hard to shake the feeling that maybe she’s been painted into a creative corner by those most interested in her success, that a Grammy sweep for this almost great record could render stifling expectations on a new artist that still needs room to grow and space to live.