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Ten Times the Grammys Actually Got It Right

Sure, music’s biggest night is often an embarrassment. But let’s toast those rare winners who were absolutely deserving, from the Beatles to Billie Eilish.

The Grammys are Sunday, and you know what that means: Another chance for everyone to complain about how the Recording Academy always screws up. And, granted, it’s awfully tempting to mock some of their past choices — Tony Bennett won Album of the Year for an Unplugged disc, the voters couldn’t get enough of Macklemore, etc. — but for the sake of argument, let’s actually take a look back at some of the times when the Academy got it right. Maybe it’s a stopped-clock-twice-a-day sort of situation, but nonetheless, I’ve come up with 10 wins that Academy members should be proud of.

But, first, some quick ground rules: I’m only spotlighting wins in the four major categories, which are Album of the Year, Record of the Year, Song of the Year and Best New Artist. (What’s the difference between Record and Song? Put simply, Record goes to the actual recorded song — that thing you hear on Spotify — while Song is for the writing of that tune.) Also, because of the Grammys’ weird eligibility rules, they don’t count calendar years as the cutoff. (For instance, Sunday’s awards cover releases from between September 1, 2019 and August 31, 2020.) 

What’s most important to remember, though, is that the Grammys are bad — except in the below instances. These albums, artists and songs were so good even the Recording Academy couldn’t screw it up.

Album of the Year (1968): The Beatles, Sgt. Pepper’s Lonely Hearts Club Band 

For decades, the Fab Four’s Summer of Love album has been considered the greatest record ever made. Even if you think that’s overrating Sgt. Pepper’s, there’s no denying its cultural importance, which is why it’s downright miraculous that the Grammys were hip enough to award the Beatles the top prize. Here was an album in which the biggest band in the world reimagined itself, crafting a fictitious persona and concentrating on studio-centric songs that treated the LP as a work of art, not just a depository for a handful of singles and some bland filler. The imaginative cover, the epic sweep, the mind-blowing finale “A Day in the Life,” in which the whole world seemed to literally explode at the end: Sgt. Pepper’s set a template that musicians have aspired to match for decades. And when you consider that the Academy had, to that point, never awarded Album of the Year to a rock record — Frank Sinatra and Barbra Streisand were winners in previous years — the achievement is even more impressive. But to give the Grammys their due, the voters were already aware of how titanic this band was: The Beatles won Best New Artist three years earlier. 

Record of the Year and Song of the Year (1971): Simon & Garfunkel, “Bridge Over Troubled Water”

It was a good Grammy night for Paul Simon and Art Garfunkel considering that Bridge Over Troubled Water also won Album of the Year. But the nod goes to the title track, which remains one of the most comforting, transcendently beautiful songs in the history of popular music. (“I have no idea where it came from… It just came, all of a sudden,” Simon once said of the song’s origins. Indeed, pianist Allen Toussaint famously marveled, “That song had two writers: Paul Simon and God.”) It’s also a terrific showcase for Garfunkel’s otherworldly voice, which offers such solace to the listener “when you’re down and out.” It’s very easy to be snide about the unvarnished sincerity of “Bridge Over Troubled Water,” a heartrending ballad that doesn’t hide its sentimental streak — or its belief that a stately piano and a stirring string section can help lift your spirits when you really need it. Sappy, maybe? Emotionally overwhelming? Unquestionably. 

Album of the Year (1977): Stevie Wonder, Songs in the Key of Life     

A 25-time Grammy winner, Stevie Wonder collected three Album of the Year prizes in the 1970s. (If Taylor Swift wins on Sunday for Folklore, she would join him, Paul Simon and Frank Sinatra as the only solo artists to have earned the prize three times.) Following his victories for Innervisions and Fulfillingness’ First Finale, Songs in the Key of Life wasn’t just a triumph but also a culmination of the genius’ astonishing run of records that had started with 1972’s Music of My Mind. Originally packaged as a double album that included an extra EP, Songs overflowed with sonic ideas, its 21 tracks ranging from romantic odes (“Knocks Me Off My Feet”) to societal commentary (“Black Man”) to proud proclamations about being a new dad (“Isn’t She Lovely”). “Pastime Paradise” inspired Coolio’s “Gangsta’s Paradise,” while Will Smith swiped “I Wish” for “Wild Wild West.” It’s a generously overstuffed record that never stops giving. 

Album of the Year (1978): Fleetwood Mac, Rumours     

The legend around the making of this album is almost as enticing as the songs contained within. The band members’ romantic relationships were falling apart — principally, the one between Lindsey Buckingham and Stevie Nicks — and so they turned their heartbreak into incredible tunes about disillusionment and pain. Because of its arrival in the midst of the laidback, easy-listening 1970s musical scene, Rumours has sometimes been dismissed as “only” a pop record, but in recent years its reputation has continued to grow as the record’s stunning level of craft and emotional acuity stuns new listeners. Not unlike Steely Dan, whose Aja competed with Rumours in the Album of the Year category, Fleetwood Mac were making exquisitely produced bon mots that contained a lot of weariness and misery underneath. “Easy listening”? Rumours is silky and catchy as hell, but there’s no mistaking all the tumult coming out of those gorgeous hooks.

Album of the Year (1984): Michael Jackson, Thriller     

Long before devastating sexual-abuse accusations came out against the King of Pop, he was known as a trailblazer who helped break MTV’s color barrier. Thriller changed the idea of what a pop superstar could be as Michael Jackson dominated this new medium known as the music video, concocting eye-catching clips that were as ingenious as the songs that accompanied them. “Beat It” daringly mixed pop with rock — Eddie Van Halen provided the fiery guitar — while “Billie Jean” was a song of betrayal and paranoia that you couldn’t stop dancing to. Seemingly everybody owned Thriller, and critics loved it, too: It won that year’s prestigious Village Voice music poll. The revelations about Jackson’s personal life have deservedly clouded his legacy, but nearly 40 years later, this remains a colossal album — one that’s influenced generations of artists across a range of genres. And it still sounds great. 

Best New Artist (1991): Mariah Carey

This category has long been derided for honoring unworthy artists, but to be fair, it can be hard to know for sure who’s going to have an enduring career — and, conversely, who will end up being Arrested Development or Men at Work, to name just two acts that won the prize and didn’t end up having much of a shelf life. But Mariah Carey’s victory looks especially good 30 years down the line. Though she’s never been given the same amount of respect as other pop superstars, you can’t argue with her longevity: She’s been making multi-platinum albums for decades, outlasting acts like Janet Jackson, Britney Spears and Celine Dion on the charts. In the process, she’s more than earned the title of a diva — a term that has a complicated, sexist history but which she wears with regal authority. The first song off her first album was the massive hit “Vision of Love,” which showed off her incredible vocal range — since then, she’s glided from hip-hop to R&B to one of the most beloved of all Christmas songs, never breaking her stride.  

Album of the Year (2011): Arcade Fire, The Suburbs     

Going into the final award of the evening, Arcade Fire didn’t have much reason to be hopeful. After all, they’d only received three nominations — Eminem, who was also up for Album of the Year (for Recovery), had 10 nominations — and hadn’t won in either of the other categories. So it was a pleasant shock when The Suburbs took home the big prize. For years, indie acts had to content themselves with winning Best Alternative Music Album and maybe getting an Album of the Year nod, but never having a shot against their pop and hip-hop competition for the top award. The Suburbs changed all that, serving as the coronation of one of rock’s best new groups, who at that point had produced three straight terrific albums. An exploration of domesticity and suburban angst, The Suburbs was a rare critics’ darling that actually impressed the Grammys, which often favors commercial success over all else. (Even Kanye West was happy with the result.) Arcade Fire’s subsequent efforts haven’t been as singular, but that doesn’t detract for how great this album — and this win — was. By the way, it’s still the band’s only Grammy. 

Album of the Year (2019): Kacey Musgraves, Golden Hour    

There were some excellent contenders this year — including Invasion of Privacy, Dirty Computer and the Black Panther soundtrack — but Kacey Musgraves’ third studio record (not counting A Very Kacey Christmas) was the deserving winner. The country artist, who had angered conservative listeners earlier in her career by daring to suggest, on “Follow Your Arrow,” that, hey, maybe same-sex relationships are a totally fine thing, went big with Golden Hour, merging country, pop, folk and disco on songs that chronicled her happy marriage (“Golden Hour”) and lingering insecurities (“Happy & Sad”). In the Trump era, this record’s hard-earned optimism and simple decency felt like a tonic. Alas, the marriage that framed Golden Hour’s most moving songs didn’t last, but the album already feels like a classic.  

Record of the Year and Song of the Year (2019): Childish Gambino, “This Is America”

Years from now, you’ll be able to tell your kids what it was like when “This Is America” dropped out of nowhere, hitting listeners like a thunderbolt. Before the song was released in early May 2018, Donald Glover had enjoyed plenty of success as a rapper-turned-R&B artist (Childish Gambino) and as the creator of the acclaimed series Atlanta. But “This Is America,” which became available online during his appearance on Saturday Night Live, was something else: an anguished, feverish bulletin that somehow encapsulated all of the country’s anger and confusion over racism, police brutality and gun violence in under four minutes. 

Part of what made the song so powerful was its shifting styles, moving from gospel to trap, as if all of Glover’s ideas couldn’t be contained in one genre. “This Is America” also won the Grammy for Best Music Video, and indeed the Hiro Murai-directed clip added a stunning visual complement to the song’s dazzling fury. As the Black Lives Matter movement continues to grow, this song remains at the center of the cultural conversation. 

Record of the Year and Song of the Year (2020): Billie Eilish, “Bad Guy”

No one had won all four major Grammy categories in 40 years. Then came Billie Eilish. Of all her trophies, though, I’m most pleased with Record of the Year and Song of the Year, which went to When We All Fall Asleep, Where Do We Go?’s smash single. The minimalist brilliance of “Bad Guy” introduced the world to Eilish, who was all of 18 when she triumphed at the Grammys, demonstrating that she was already a full-fledged artist with a sharp, sardonic perspective. Inescapable both on the radio and in your head, “Bad Guy” spit in the eye of macho dudes who thought they could impress her — she’s as tough as the beat banging in the background. “My mommy likes to sing along with me / But she won’t sing this song,” Eilish brags. “If she reads all the lyrics / She’ll pity the men I know.” Who knows if she’ll be an all-timer or merely a musician of the moment. But she’s rightly ruled the last couple years.

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