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 fanbase, 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 she 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 front to back.
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 albums 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 her a particularly potent Grammy force, the way that only a couple artists in a decade tend to be.
And while 18 years of age would seem to put her in opposition to the classical image of an award-show juggernaut, it's hasn't been as big a past detriment at the Grammys than you might think. Eilish did become the youngest album of the year winner, but not by a particularly dramatic distance: Taylor Swift was 20 when she won in 2010 for Fearless, and Alanis Morissette 21 in 1996 for Jagged Little Pill. Look further down the list of the youngest AOTY 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 fanbase 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 '90s 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), Billie herself is actually a fairly unthreatening presence for concerned moms and dads of the world: Neither her lyrics or 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, who they shouted out in the audience in one of their many acceptance speeches last 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 Billie 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 Billie 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 on 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, as she wasn't a listed writer on her "Don't Know Why"), found success for the remainder of the '00s, 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 Christopher 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 last 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 off the stage). 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 or not 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 could probably 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 affect that has on her insider industry approval. You could maybe see Billie 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 fanbase, but sent the casuals packing.
In any event, despite arriving at such a seemingly desirable climax last 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 Bond 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.