Grammys: Behind Billie Eilish's Big-Four Sweep and What It Means for Her Career

Now that she's essentially achieved the highest level of mainstream recognition and attention that a young artist can receive, will she look to shed the spotlight a little in future years?

Imagine telling a Billie Eilish fan two years ago — when she was a 16-year-old burgeoning cult star known for her massive online following, eccentric fashion sense and oddball alt-pop singles — that in 2020, she'd have the kind of Grammy success only one other artist in over 60 years has ever had. They'd probably either think you were lying, or assume that Eilish's music and image had taken a wild turn towards the conventional from the weirdo teen artist they currently knew.

Nope. On Sunday night, Eilish did in fact become the second artist in Grammy history to win in all of the Big Four categories: best new artist, album of the year (for full-length debut When We All Fall Asleep, Where Do We Go?), song of the year and record of the year (both for "Bad Guy"). And she didn't do it by pandering to or changing for anybody: If anything, her music is more unpredictable, challenging and singularly Billie (and co-writer/producer Finneas) than ever before, as is her decidedly uncompromising fashion and unpolished public persona.

So how did the green-haired, lollipop-sucking 18-year-old with the sunglasses and the devilish grin that we saw last night become a Grammy darling of such historic proportions? Well, it certainly starts with that cult fan base, which, over the course of the not-even-half-decade since Eilish's first single, has grown exponentially. Despite still feeling like an alternative artist, she's now doing decidedly pop numbers — selling out an arena tour in days, launching 12 of the 14 tracks on When We All Fall Asleep onto the Billboard Hot 100 (including an eventual No. 1 smash in "Bad Guy") and not only debuting atop the Billboard 200 with Asleep, but also topping the chart's year-end listing.

Though the biggest awards at the Grammys don't always go to the biggest hits — see last year's album of the year winner, Kacey Musgraves' Golden Hour, for a solid counter-example — having that level of commercial success is a huge advantage in the biggest categories, as recent blockbuster successes and big-time Grammy winners like Adele, Bruno Mars and Taylor Swift will all tell you. And though Eilish was far from the only artist with major hits to have been up for the biggest Grammys this year, only Ariana Grande could really match the combination of albums and singles success that Eilish had in 2019. And while Grande's run felt like it was piggybacking a little on her Sweetener from 2018, with her momentum petering out a little in the year's back half, Eilish basically owned the calendar from start to finish.

It wasn't just commercial success that Eilish had on her side, though: She also became one of the year's best-reviewed artists for Asleep, which topped a number of publications' best-of-2019 lists, and finished in a high position pretty much across the board. Again, she wasn't the only critical favorite to be in contention for the major awards — Lana Del Rey and Vampire Weekend attracted similarly strong reviews for their respective contending albums, as again did Grande — but the combination of rave reviews with blockbuster sales made Eilish a particularly potent Grammy force, the way that only a couple artists in a decade tend to be.

And while her young age would seem to put her in opposition to the classical image of an awards-show juggernaut, it hasn't been as big a detriment at previous Grammys as you might think. Eilish did become the youngest album of the year winner, but not by a particularly dramatic distance: Swift was 20 when she won in 2010 for Fearless, and Alanis Morissette was 21 when she won in 1996 for Jagged Little Pill. Look further down the list of the youngest album of the year winners to Barbra Streisand, Lauryn Hill and Adele and you'll notice a common trend: They're all female. For whatever reason, the Recording Academy has been historically kind to prodigious young female artists, with Eilish just being the most extreme example to date.

What's more, though Eilish's fan base skews unmistakably Gen Z, she isn't as alienating to older audiences as a traditional teen star. Due to her left-field approach to pop and the convention-shattering image she displays in her fashion and videos, parents of her young fans can easily recognize the legacy of any number of their own 1990s alt heroes in her music, from Trent Reznor of Nine Inch Nails to Shirley Manson of Garbage to Billie Joe Armstrong of Green Day, the latter an avowed hero (and Rolling Stone cover co-star) of Eilish's. And despite the rebellious-teen attitude of her music and look (and the stray "might seduce your dad" lyric), Eilish herself is actually a fairly non-threatening presence for concerned moms and dads of the world: Neither her lyrics nor her image are particularly aggressive or sexually provocative, while her closest artistic collaborator is her older brother. Hell, the siblings even seem to have a good relationship with their own parents, whom they shouted out in the audience in one of their many acceptance speeches on Sunday night.

Good relationships in general might also be at the core of Eilish's tremendous Grammy success. While she and Finneas were growing her brand last year, they said yes to seemingly ever major media opportunity — with magazines, with streaming services, with industry events far and wide. Absolutely everybody wanted a piece of Eilish in 2019, and for the most part, she was willing to give one to just about whoever asked. And while she's unrehearsed, unpredictable and usually foul-mouthed as an interview subject or honor recipient, she's also funny, refreshing and generally charming in nearly all her media appearances — while rarely being too bad-behaved to get herself (or anyone else) in all that much trouble. It all resulted in an industry of Grammy voters wanting to root for Eilish, which certainly couldn't have hurt when it came time to cast their votes in the Big Four categories.

Of course, the day after Eilish went four-for-four in those categories, it's hard not to already ask the question: Was it too much? Can anyone win that big on that level and still maintain the scrappy underdog reputation and following that got them to that point? It's a fair concern, especially given the history: Christopher Cross, the yacht-rock singer-songwriter who was the only artist before Eilish to sweep the Big Four categories, undoubtedly saw his career peak that night in 1981, as his next album fared only about a fraction as well commercially and he was essentially done in popular music by the mid-decade. Even Norah Jones, whose music reigned victorious in all four major general categories in 2003 (though Jones herself did not receive song of the year honors, as she wasn't a listed writer on her "Don't Know Why"), found success for the remainder of the 2000s, but was never again quite the sensation that she was on 2002's Come Away With Me. Could Eilish be in for a similar fate following this year's ceremonies?

It's possible, certainly, but it's unlikely that there will actually be a backlash like the one Cross received following his Grammy success, which essentially turned his historic night into a long-running pop punchline. Cross, while a talented singer-songwriter, was a near-comically safe choice as a Grammy favorite, representative of an unchallenging soft-rock era that was just minutes away from expiring as the '80s turned their focus to MTV and new wave. While she has now been approved of by the establishment, there's little risk of Eilish suddenly coming to feel like an establishment figure — even on Sunday night, her discomfort at being at the center of such a continuous ringing endorsement was increasingly visible, to the point where she could be seen pleading to not have to give her fourth acceptance speech of the night (which she then kept to two words before darting offstage). Casual fans may need a short break from her after Sunday, but it's doubtful they'll decide they're done with her entirely.

The better question, though, may be whether Eilish herself will decide to pull back from the mainstream after this. Now that she's essentially achieved the highest level of mainstream recognition and attention that a young artist can receive, will she look to shed the spotlight a little in future years? It might be tough for her to do with her music alone, since you can't really shock your audience with a sonic left turn when your popularity is already based on a career of such swerves. But she probably could find a way out of Top 40 radio with a daring-enough change of direction, at least — and in the meantime stop playing the media game to such a degree and see what effect that has on her industry approval. You could maybe see Eilish loosely following the career path of Twenty One Pilots, who were also pop and Grammy darlings (albeit on a smaller scale) a few years ago before releasing a dense, highly conceptual next album with a largely abrasive lead single — all of which thrilled and consolidated their considerable core fan base but sent the casuals packing.

In any event, despite arriving at such a seemingly desirable climax on Sunday night, Eilish's career has felt anything but scripted to this point, so it's unlikely that it will continue to follow a clean narrative from here. Maybe further pop triumphs await, or maybe a commercial receding is due — the only thing we know for sure about Eilish's 2020 plans beyond an upcoming world tour is that her and Finneas' attempt at a James Bond film theme awaits, an opportunity that carries the unpredictable "sure, why not?" charm that's marked most of their success to date. It was a dream night for the sibling duo, but as Eilish herself alludes to in the title to her Grammy-winning LP, neither she nor anyone else has any idea where such dreams may take her.

This story first appeared on Billboard.com.