64 Grammys, 64 Moments: The Greatest Moment From Every Grammys Ceremony So Far

At the inaugural Grammys — held simultaneously on both coasts and untelevised — Frank Sinatra was likely the biggest (and certainly the most-nominated) star of the evening. However, despite his six nods, he was shut out of the big categories, with his future standard “Witchcraft” losing both song and record of the year to Domenico Modugno’s Italian-language Billboard Hot 100-topper “Nel Blu Dipinto Di Blu (Volaré).” However, he didn’t go completely snubbed: Sinatra won best album cover photography as art director of his Frank Sinatra Sings for Only the Lonely album. 

That above year isn’t a typo: Despite the Grammys debuting in May 1959, the second such ceremony was held just six months later, in November of the same year. However, for much of America, it may as well have been the inaugural Grammys, as this was the first year that the awards were televised, premiering as a pre-taped event on NBC Sunday Showcase. Viewers got to see Sinatra vindicated for his near-shutout the year before with an album of the year win for his Come Dance With Me!, though the big winner of the night was breakout crooner Bobby Darin, who took home both best new artist and record of the year (for his Hot 100-conquering “Mack the Knife”). 

The most interesting part of the Grammys’ third year — and yes, they skipped 1960 and held the third ceremony in April of ’61 — might not have been anything that happened at the ceremony, but the Recording Academy’s official adoption of a set of Grammy standards (penned by rock-hating satirist Stan Freberg, of all people), generally referred to as the “Grammy Credo.” “We shall judge a record on the basis of sheer artistry, and artistry alone — artistry in writing, performance, musicianship and engineering,” wrote Freberg. “Sales and mass popularity are the yardsticks of the record business. They are not the yardsticks of this Academy.” 

Though it had already been nearly a decade since Elvis Presley’s and Chuck Berry’s breakouts, it wasn’t until 1962 that the Grammys first introduced a rock category: best rock and roll recording. In its first year, the award went to Chubby Checker for his sequel smash “Let’s Twist Again,” triumphing over James Darren, Chris Kenner, The Tokens and Ike and Tina Turner. “In those days, rock and roll was considered a dirty type of music that nobody appreciated,” Checker remembered in 2016. “And then we won a Grammy.”

After airing the second ceremony on prime time with relative success, the next two Grammys were again untelevised — until 1963, when they returned to NBC, this time under the program title The Best on Record. “For the next 60 minutes, you’re going to see the finest the record business has to offer,” promised Frank Sinatra to viewers by way of introduction, and the ensuing hour would include a three-song medley performed by Henry Mancini on piano, as well as music-themed standup by comedian (and previous album of the year winner) Bob Newhart, and a lifetime achievement award for legendary singer Bing Crosby. The Best on Record would air in similar fashion through 1970.

Few better ways to demonstrate the longevity of star entertainer Barbra Streisand than pointing out that she won two Grammys, including album of the year, as a 22-year-old — at the time, the youngest-ever winner in the marquee category — a whopping 59 years ago, back when her AOTY competition included Al Hirt, The Swingle Singers and The Singing Nun. Haven’t seen those other names around the Grammys much lately, but Streisand was nominated for best traditional pop vocal album just six years ago.

By ’65, the British Invasion had officially become unignorable on U.S. shores — meaning The Beatles were finally primed to make a Grammy impact. It was far from a clean sweep for the Fab Four — their “I Want to Hold Your Hand” lost record of the year to Stan Getz & João Gilberto’s “The Girl From Ipanema,” and “A Hard Day’s Night” fell in best rock and roll recording to Petula Clark’s “Downtown” — but they did win best new artist and best performance by a vocal group (for A Hard Day’s Night), while picking up an unofficial third W for The Chipmunks’ The Chipmunks Sing the Beatles set, which took home best engineering recording – special or novel effects. 

While the mid-’60s were halcyon days for rock, soul and folk in the U.S., it was a country song that cast the largest shadow of the ’66 Grammys: Roger Miller‘s drifters’ anthem “King of the Road,” winner of five statues on the evening — including, curiously, the just-rechristened “best contemporary (R&R) single,” a rock category also encompassing The Beatles’ “Yesterday” and Tom Jones’ “It’s Not Unusual.” The surest sign of the song’s outsized impact, though, was that even its answer song — “Queen of the House,” by the unrelated Jody Miller — took home the Grammy for best country & western vocal performance – female.

The major categories at the ’67 Grammys saw a music industry at a crossroads, with old-world titan Frank Sinatra winning record and album of the year (for “Strangers in the Night” and A Man and His Music, respectively), and John Lennon and Paul McCartney of youth vanguard leaders The Beatles taking home song of the year (for “Michelle”). But curiously, the fourth major Grammy category, best new artist, was nowhere to be found — for the only time since its introduction at the second Grammys, the award was not presented. The reasons why remain unclear, though it’s not likely to have been for a lack of acceptable choices: Simon & Garfunkel, Percy Sledge and the Chairman of the Board’s own daughter Nancy would’ve all likely been eligible. 

In 10 years, the Grammys had grown from “Volare” to Sgt. Pepper’s Lonely Hearts Club Band — ’68 winner for album of the year — and the show celebrated its evolution with a medley performance of past song of the year winners. Country stars Glen Campbell, Bobbie Gentry and Chet Atkins were joined by jazz-pop singer Jack Jones for the medley, which closed the show, and arguably marked the first time that the Grammys officially had enough history of their own to self-anthologize. 

Excitement for the ’69 Grammys was dampened slightly by a two-month tape delay, which included the holding of the record of the year winner announcement until one of five pre-prepped announcements was read aloud on the May NBC special. More warmly received than that pre-taped footage was a proto-music video filmed by Simon & Garfunkel for their “Mrs. Robinson” — the award’s eventual winner — a clip of the folk-rock duo doing their best Joe DiMaggio impressions at an empty Yankee Stadium, ending up halfway between The Monkees and Dinosaur Jr’s “Feel the Pain.” 

The big winners of the 12th Grammys were mostly pop-rock hitmakers like The 5th Dimension (record of the year, “Aquarius/Let the Sunshine In”) and Blood Sweat & Trears (album of the year, Blood Sweat & Tears). But lower on the bill, a much more innovative artist was cleaning up: the composer then known as Walter Carlos took home three Grammys for Switched-On Bach, an unlikely crossover hit of modernized classical that helped bring the synthesizer into the popular consciousness. Carlos’ wins would later prove a landmark for a different reason: Walter had already begun gender transitioning in the early ’70s, and would come out as Wendy Carlos in 1979. 

In its 13th year, the Grammys finally made the move to the live telecast that has continued until today, with pop veteran Andy Williams hosting the event live from the Hollywood Palladium in California and ABC picking up the broadcast. All five of the song of the year nominees were performed on the show, though The Carpenters were the only artist to play their own nominated song (“We’ve Only Just Begun”), with memorable covers including Dionne Warwick taking on The Beatles’ “Let It Be” and Aretha Franklin doing Simon & Garfunkel’s “Bridge Over Troubled Water” — the eventual winner.

While such female artists as Barbra Streisand, Judy Garland and Bobbie Gentry had emerged as big winners in Grammys past, it wasn’t until ’72 that they triumphed in all four of the major Grammys categories. It helped that it was the year of Carole King‘s Tapestry — a commercial behemoth that topped the Billboard 200 for 15 consecutive weeks in ’71 and led to King winning album of the year, as well as song of the year (“You’ve Got a Friend”) and record of the year (“It’s Too Late,” with Lou Adler). A pre-“You’re So Vain” Carly Simon picked up best new artist to complete the all-female sweep. 

While venerated singer-songwriter Charley Pride had already won a pair of awards at the 14th Grammys — best sacred performance (“Did You Think to Pray”) and best gospel performance (other than soul gospel) (“Let Me Live”) — in ’73, he made history by taking home best country vocal performance – male for his Charley Pride Sings Heart Songs LP. The win made him the first Black performer to win in the country vocal categories, with The Pointer Sisters (“Fairytale,” 1975) and Darius Rucker (“Wagon Wheel,” 2014) being the only other two artists to follow in his footsteps since. 

At the ’74 ceremonies, returning host Andy Williams announced that the Recording Academy would be taking another step to solidify the Grammys’ enduring legacy with the introduction of the Grammy Hall of Fame. According to the Grammys website, the Hall is intended to “honor recordings of lasting qualitative or historical significance that are at least 25 years old,” which are “selected annually by a special member committee of eminent and knowledgeable professionals from all branches of the recording arts.” The inaugural ’74 class welcomed Coleman Hawkins’ “Body and Soul,” Nat King Cole’s “The Christmas Song,” Paul Whiteman’s recording of “Rhapsody in Blue,” Louis Armstrong & His Hot Five’s “West End Blues” and Bing Crosby’s “White Christmas” to its ranks.

Glam superstar David Bowie was in full Man Who Fell to Earth mode when he took the stage at the ’75 Grammys to present the award for best R&B vocal performance, female. “Ladies and gentlemen… and others,” an unnervingly gaunt and distracted-looking Bowie drawled. “My personal award is having the opportunity to salute… ces premieres femmes noir.” He put on sunglasses to read the recipient: Aretha Franklin, for “Ain’t Nothing Like the Real Thing,” who subsequently declared, “Wow, this is so good I could kiss David Bowie!” The Thin White Duke — who would admit to being on significant amounts of cocaine at the time — later summarized his appearance as “strange, strange, strange.” 

Stevie Wonder was on a Grammy tear never quite seen before or since in the mid-’70s, winning album of the year three out of four years, in ’74 (Innervisions), ’75 (Fulfillingness’ First Finale) and ’77 (Songs in the Key of Life). The one gap year was in ’76, where the rest of the AOTY nominees had the good fortune of Wonder not having a new album eligible. Eventual winner Paul Simon (for Still Crazy After All These Years) acknowledged his luck in not having to go up against the onetime 12-Year-Old Genius in his acceptance speech: “Most of all, I’d like to thank Stevie Wonder, who didn’t make an album this year.”

The Grammys attempted to extend their reach beyond the Western world in ’77, transmitting for the first time to Hong Kong. (“I can just picture a Chinese family sitting in front of their television set with their chop sticks in hand watching all this silver and all this glitter and singing a gospel song-along with the Oak Ridge Boys,” quipped Andy Williams, hosting for the seventh and final year.) What’s more, Grammy juggernaut Stevie Wonder beamed in live all the way from Lagos, Nigeria — though it might’ve been a touch too far for the telecast to handle, as technical difficulties plagued what should’ve been a triumphant performance of smash hit “Sir Duke.”

For the first (and to date, only) time in the 20-year history of the Grammys, 1978 saw a split decision in one of the Big Four categories. Song of the year was presented to Barbra Streisand and Paul Williams for Streisand’s “Evergreen (Love Theme From ‘A Star Is Born’)”… who then ceded the mic to songwriter Joe Brooks, who was also a winner for Debby Boone’s “You Light Up My Life.” The most remarkable thing about the dual W? It wasn’t even the first time Babs had tied for a major award, having to share her Oscar win for best actress (for Funny Girl) in 1969 with Katharine Hepburn (The Lion in Winter). 

The disco era was in full effect in both music and fashion by the ’79 Grammys, with second-time host John Denver joking, “I look out here at all the members of the Recording Academy and I see a lot of silks and satins and jewelry and new hairstyles — and gee, the ladies look fantastic too!” No surprise then, that the awards — which aired on Thursdays back in the late ’70s — went straight Saturday Night Fever, with the hit Travolta film’s accompanying album becoming the first film soundtrack ever to win album of the year, and the set’s linchpin artist the Bee Gees picking up an additional three statues for their efforts. 

Famed hitmakers and fellow Brooklynites Barbra Streisand and Neil Diamond had never performed their 1978 Hot 100-topping duet “You Don’t Bring Me Flowers” together — until the two made a surprise appearance together at the ’80 Grammys to deliver an emotionally overpowering rendition of the classic ballad. The performance brought the house down and is often cited as one of the greatest in Grammy history, with longtime producer Ken Ehrlich — then working on his first Grammys — later saying that “in terms of the modern era, it was the first ‘Grammy Moment.’ We’ve tried to equal it ever since.”

In 1981, Christopher Cross managed a Grammy feat no artist had before, or for nearly 40 years after: He won each of the Big Four categories, including song and record of the year for his Hot 100-besting “Sailing,” and album of the year for his self-titled debut. (Norah Jones was also the credited artist on each Big Four win in 2003, but did not win song of the year herself for “Don’t Know Why,” as she was not a credited writer of the song.) Cross, who deemed his quartet of major Grammy wins a “dream come true,” never won at the awards again — though he did pick up an Oscar for his Arthur composition “Arthur’s Theme (Best That You Can Do).” 

Following his 1980 assassination by Mark David Chapman, John Lennon‘s Double Fantasy album (a collaboration with wife Yoko Ono) became one of the most successful of his solo career, climbing to No. 1 on the Billboard 200 while single “(Just Like) Starting Over” did the same on the Hot 100. The album was eventually nominated for a pair of Grammys, winning for album of the year. A visibly emotional Ono accepted the award on behalf of the two, and was greeted with an extended standing ovation. “Both John and I were always very proud and happy that we were part of the human race,” she said, “who make good music for the earth, and for the universe.” 

Toto had plenty of thanks to go around at the 25th Grammys, as they won a combined five Grammys on the night, most for their Toto IV album and its hit lead single “Rosanna.” So by the time the collective won for producer of the year — beating Quincy Jones, among others — singer/songwriter David Paich specifically singled out Los Angeles Times critic Robert Hilburn “for believing in us all these [years].” The audience’s chuckling response and Paich’s own smirk made his level of sincerity clear for the shout-out, and indeed, Hilburn had taken a variety of shots at the band over the years for what he saw as their “artistic dubiousness.” 

By the time of the ’84 awards, MJ was unquestioned as the biggest pop star on the planet, with MTV turning him into a multi-platform sensation and his Thriller album well on its way to becoming the greatest-selling album in music history. The Grammys weren’t exactly a show-length coronation for the singer — his “Billie Jean” lost song of the year to The Police’s “Every Breath You Take” — but he did win eight awards, including record of the year for “Beat It” and album of the year for Thriller, eventually opting to call up proxies like label boss Walter Yetnikoff and sisters Janet, Rebbie and La Toya to accept the trophies in his stead. 

A moment never to be replicated: Howard Jones, Herbie Hancock, Thomas Dolby and Stevie Wonder playing synths in the round, a four-way “showdown” meant to show pop’s push into the future, which today looks 100 times more dated than a ’40s black-and-white MGM musical. But the time capsuleness of the medley, encompassing hit ’80s songs by each (and “America the Beautiful,” for some reason), is absolutely singular — down to the hairstyles, the jackets, the lighting, and the disembodied MacInTalk voice directing the whole production. 

Woke before woke, the ’86 Grammys were dominated by the social conscience of the time, following the tremendous mid-’80s success of charity supergroups Band Aid and USA for Africa — the latter ending as one of the night’s big winners, taking home record and song of the year, for Quincy Jones and the duo of Michael Jackson and Lionel Richie, respectively. The tone was set by a deeply ponderous, tuxedo’d performance by Police frontman-gone-solo Sting, of his overwrought cold war protest “Russians” — a performance, in its own way, as surreal today as the previous year’s Synth Showdown.

While spreading world music (and/or cultural appropriation) with his fantastically successful 1986 solo album Graceland, Paul Simon also took over the ’87 Grammys, both winning album of the year and opening the show with a triumphant performance of “Diamonds on the Soles of Her Shoes.” The above comment was host Billy Crystal’s quip about Ladysmith Black Mambazo, the South African male choral group featured on the song and in Simon’s performance.

MJ may have made his mark on the ’84 Grammys, but he didn’t actually perform at music’s biggest night until 1988, when he stole the show with a rare two-fer performance of a pair of Bad chart-toppers: “The Way You Make Me Feel” and “Man in the Mirror.” While “The Way” was all about MJ’s choreography — he didn’t even bother with a mic to help make his lip-syncing plausible — MJ unleashed his pipes for the extended outro to “Mirror,” an ad-libbed three minutes of peerless vocal rapture that continues to reverberate three decades later. 

In the late ’80s, metal had become such an inextricable part of the mainstream that the Grammys finally had to acknowledge the category with its own category: best hard rock/metal performance vocal or instrumental. But while the category recognized such hard rock leading lights as Metallica and Jane’s Addiction, the award ended up going to Crest of a Knave, the 16th album from prog-rock wheeze kids Jethro Tull. The decision was widely mocked inside and outside of the metal community and today stands as one of the go-to examples of the Recording Academy’s sizable learning curve when recognizing new forms of music. (See also in 1989: no nominations for N.W.A or Public Enemy in the newly introduced best rap performance category, which went to DJ Jazzy Jeff & the Fresh Prince.)

Speaking of Public Enemy: In the second year of best rap performance, they were recognized, for the beyond-iconic Do the Right Thing anthem “Fight the Power” — but lost to pop-rap crossover smash “Bust a Move,” by Young MC. During the rapper’s acceptance speech, though, resident PE jester Flavor Flav decided to crash the stage to interrupt — not to protest the win, but rather just to hug and congratulate his competition. “I’d like to thank Flavor Flav for breaking up the monotony of my acceptance speech,” Young MC kept rolling. “Hey, you’re welcome!” barked Flav, before exiting stage right. 

The onset of the ’90s saw the debut of a 20-year-old who would go on to define pop for much of the next two decades, and her arrival was marked at the ’91 Grammys with a powerhouse performance of debut Hot 100-topper “Vision of Love,” announcing her rookie presence with authority like Kobe Bryant at the ’97 dunk contest. Mariah Carey would also take home the awards for best new artist and best pop vocal performance, female, and following the ceremony, her self-titled album sprang to the top of the Billboard 200, beginning an 11-week reign at No. 1.

Few pop songs have the power to make time stand still like Bonnie Raitt‘s “I Can’t Make You Love Me,” and the singer froze the entire music world at the ’92 Grammys with her trembling performance of her signature ballad. That Bruce is Hornsby, not Springsteen, by the way — the piano man accompanied Raitt on both the recording and this performance, and his piano ad libs stoke the song’s embers throughout, keeping it burning bright and slow till the end. In 2016, “I Can’t Make You Love Me” was inducted into the Grammy Hall of Fame. 

That was host Garry Shandling in the midst of Clapton’s dominant run at the ’93 Grammys, where the guitar great took home six awards. Those included album of the year, for his eventually Diamond-selling MTV Unplugged set, and both song and record of the year for his devastating power ballad “Tears in Heaven” — which also perhaps provided the most indelible memory of Clapton’s evening, via his graceful, near-spiritual performance of the soundtrack smash, written following the tragic death of his son Conor. Still, Clapton felt undeserving: “I don’t think I deserved to win this — there were better songs,” he commented after one of his many Ws. “But I’m very grateful.”

Frank Sinatra, the earliest Grammys legend, was the recipient of the Grammy Legend award at the ’94 awards, and received a rambling, if affectionate, introduction from Duets partner Bono of U2. But the Chairman of the Board’s own sprawling acceptance speech — which included his raw feelings about not being asked to sing at the ceremony — was cut off early by the Grammys for a commercial break. The call to do so was later attributed to Sinatra’s own camp, but the smart was felt throughout the awards — including by Billy Joel, who would dramatically pause his own later performance of “River of Dreams” before the final chorus, to look at his watch and sarcastically comment, “Valuable advertising time going by…” 

Women had been a virtually invisible presence among best rap performance winners in the award’s first six years, with Ladybug of 1994 winners Digable Planets the only female MC to take home a statue in the category. That changed in ’95, when — in the fifth year of the award being split into both best rap solo performance and best rap performance by a duo or group — it was a clean sweep for the ladies, with Queen Latifah taking solo performance for her solidarity anthem “U.N.I.T.Y.” and Salt-N-Pepa winning duo or group for their anti-slut-shaming credo “None of Your Business,” shortly following a thrashing performance of the jam.

Despite its major role in ’90s music culture, grunge never had a huge presence at the Grammys: Nirvana didn’t even win one until after frontman Kurt Cobain’s death and were never nominated in the Big Four categories. One reason why might’ve been the ambivalence of the scene’s primary practitioners toward awards in general, as exemplified by Eddie Vedder of Pearl Jam upon the group’s 1996 win in best hard rock performance (for “Spin the Black Circle”). “On behalf of all us, I don’t know what this means, I don’t think it means anything,” mumbled Vedder to apprehensive applause. “There’s too many bands, and you’ve heard it all before, but uh… thanks, I guess.” 

After lighting up the country world with her debut album Blue, 14-year-old LeAnn Rimes became the youngest artist ever to win a Grammy — beating previous holder Luis Miguel by 131 days — when she took best new artist and best female country vocal performance (for “Blue”) at the ’97 awards. “Looking back on it when I watch video of it, I see this girl who was wide-eyed and so excited,” she told People in 2017. “It was a great moment.”

It was the most chaotic and action-packed Grammys in history — you can read all about the composite craziness here — but the enduring memory from the ’98 awards is still likely of a shirtless and flailing Michael Portnoy, with the two-word non-sequitur “SOY BOMB” written in big letters on his chest. “My only real preparation was getting a blood transfusion the night before from a horseshoe crab… The blood transfusion caused those letters to form unexpectedly on my chest!” the enigmatic artist “explained” to Billboard of the motivation behind his stage-crashing. “It was horribly itchy!”

The ’99 Grammys were dominated inside and out by ex-Fugee Lauryn Hill, who won five awards (including best new artist and album of the year, for solo debut The Miseducation of Lauryn Hill) and gave a heart-rending, Carlos Santana-assisted performance of album highlight “To Zion” to boot. But the most memorable moment on the night belonged to a different gone-solo star: Menudo alum Ricky Martin, who delivered a riotous performance of World Cup anthem “The Cup of Life” that confirmed him as an international force to be reckoned with. By year’s end, not only was Martin a superstar, but several other Latin artists had taken over U.S. top 40 along with him.

One of those Latin artists able to storm the American pop scene post-Ricky Martin was cross-platform star Jennifer Lopez, who was nominated for best dance recording for her Hot 100 top 10 hit “Waiting for Tonight.” But it wasn’t her Grammy chances — she eventually lost to Cher’s “Believe” — that got people talking that night: It was her dress, a tropical-print green Versace gown with a neckline that just kept going, which captured headlines seemingly for the rest of the year. The dress cemented J.Lo as an icon and had impact well outside of the worlds of music and fashion; according to software engineer Eric Schmidt, the countless Internet queries for it post-Grammys were the inspiration for Google Image Search.

Eminem was undoubtedly the most polarizing figure in the music industry at the turn of the millennium, with untold millions of records sold and a controversy to go along with seemingly every one of them. Much of the criticism of Eminem’s music was related to the preponderance of homophobic language and sentiments in his lyrics, something Em had shrugged off as artistic license and not indicative of his actual character. To back up his words, the rapper performed his 2000 single “Stan” at the Grammys with openly gay rock legend Elton John on piano and backing vocals, a powerful performance that ended with the pair hugging. The gesture might have been more divisively received today, but it no doubt stands as one of the most unforgettable Grammy moments of the century regardless.

For the first Grammys following the 9/11 attacks, there was only one band that could really open the ceremonies: U2, whose blockbuster All That You Can’t Leave Behind album had become the sort of unofficial soundtrack to the nation’s healing after the devastating tragedy. The band delivered a stirring performance of their perseverance anthem “Walk On,” beginning the song with a Bono shout of “U! S! A!” They weren’t the only artists delivering catharsis that night, either — Mary J. Blige also performed a searingly visceral rendition of her hit “No More Drama,” a personal creed that never felt more universal. 

No surprise that punk legend Joe Strummer went largely unrecognized by the Grammys during his lifetime, since The Clash’s incendiary underground rock was hardly the kind of music Recording Academy voters favored in the era of the Bee Gees and Christopher Cross. After Strummer’s death in late 2002, however, the Grammys helped make up for lost time by assembling an all-time cast — Bruce Springsteen, Elvis Costello, Dave Grohl and Steven Van Zandt — to trade off lyrics and combine guitars on a blistering rendition of The Clash’s “London Calling,” a rare blast of unchill in a year where Norah Jones basically won everything.

Following the duo’s single “Hey Ya!” reaching a level of cultural ubiquity rarely achieved by 21st-century pop songs, OutKast had emerged as arguably both the most successful and acclaimed act in popular music by the time of the 2004 Grammys. It was no surprise, then, that their Speakerboxxx/The Love Below double album would take home the top prize of the night — which it did — except that no rap group had ever done it before, with Lauryn Hill’s rap/R&B hybrid Miseducation set being the only album from the hip-hop world to do so previously. More incredibly? Nearly two decades later, there still hasn’t been another hip-hop album to do so since. 

Still just a young’n on the scene with only a debut album to his lead credit, Kanye West‘s behavior was already a major point of discussion leading up to the 2005 Grammys, as he had made headlines for storming out of the AMAs in anger after losing best new artist to country star Gretchen Wilson. Kanye would lose best new artist (to Maroon 5) at the Grammys too, as well as a couple other major awards, but he did emerge victorious in best rap album (for College Dropout) and best rap song (for “Jesus Walks”). “Everybody wanted to know what I would do if I didn’t win,” ‘Ye commented while accepting his rap album Grammy. “I guess we’ll never know.”

The 48th Grammys featured an all-star tribute to funk paragon Sly Stone (of & The Family Stone fame), with Maroon 5, will.i.am, Ciara, Steven Tyler & Joe Perry and many more joining forces for a cover medley of the group’s biggest hits. Before launching into set-closer “I Want to Take You Higher,” Tyler welcomed Stone himself — a longtime recluse since receding from the spotlight in the early ’80s — to the proceedings, as the bandleader emerged in a silver jacket and green mohawk, mumbled through a couple of verses and choruses, and then left the stage a minute before the band finished jamming. “Can you really argue with an unbelievable-looking mohawk and a silver jacket?” asked Adam Levine of Maroon 5 after the surreal performance, which, no, you can’t.

Years after their protest of then-president George W. Bush cost them a disturbing percentage of their country fanbase, the Chicks found themselves more accepted by the music mainstream than ever, as their Taking the Long Way album earned the trio their first album of the year Grammy, while rebellious lead single “Not Ready to Make Nice” won song and record of the year. The group also offered an electrifying performance of the Hot 100 top five hit, making it clear that there were still plenty of remaining battles for the Chicks to fight once they left the awards-show stage. 

Before Taylor Swift turned it into an awards show near-cliché, Herbie Hancock had absolutely mastered the art of the OH MY GOSH YOU GUYS face in reaction to a big win. Of course, in Hancock’s case, the surprise was understandable — his River: The Joni Letters collection hardly seemed like a front-runner for album of the year amid competition like Amy Winehouse’s Back to Black and Kanye West’s Graduation. But the stunned jazz legend managed an acceptance speech through his shock: “It’s been 43 years since the first and only time that a jazz artist got the album of the year award,” he offered, not even noticing that he’d dropped his paper of prepared remarks. “And I’d like to thank the Academy for courageously breaking the mold this time.”

While unexpected big-name collaborations have been the name of the game for the Grammys for most of the 21st century, sometimes they get lucky when the titan team-ups come pre-packaged, as they did with “Swagga Like Us” in 2009. The song featured arguably the four biggest rappers in the world in the late ’00s — JAY-Z, Lil Wayne, Kanye West and T.I. — and the ’09 Grammys got all four of ’em to show up in tuxes and perform their all-world team-up. And yet, the show was stolen by overqualified hook singer M.I.A., seemingly at least 13 months pregnant, but swagger still on a hundred thousand trillion.

P!nk had no shortage of hits to choose from when she was selected to perform at the ’10 Grammys — her 2008 Funhouse album had already generated three top 20 hits, including the Hot 100-topping “So What” — but she instead opted to sing album closer “Glitter in the Air,” in a performance that featured the pop star taking to the skies for a stunning display of aerial aerobics. The soulful and technically spectacular performance resulted in “Glitter in the Air” becoming the album’s fourth top 20-charting single almost immediately, and is cited today by P!nk as the turning point in her veteran career where she became a top-line live attraction. 

The most buzzed-about awards-show performer of the late ’00s made a resounding comeback at the 2011 Grammys with a scorching performance of new single “Born This Way,” debuted just two days before the ceremony. The most notable part of Lady Gaga’s performance was its beginning, as the singer-songwriter emerged from a cocoon-like egg to perform the self-expression anthem — though she later clarified to Jay Leno that she saw the contraption as a “vessel,” not an egg. Regardless, it helped birth a smash, as “Born This Way” debuted at No. 1 on the Hot 100 and stayed there for six weeks. 

Adele had done everything but bring back the CD era in the early ’10s, with her 21 album proving a unanimously beloved commercial blockbuster, the likes of which most thought no longer possible in the post-monocultural age of digital. By the time of the ’12 Grammys, the only suspense remaining was for categories where she wasn’t nominated: Adele went six for six, including album of the year for 21, and song and record of the year for “Rolling in the Deep.” However, Adele’s pre-destined triumph was overshadowed by music-industry tragedy, as pop and R&B giant Whitney Houston had died unexpectedly before a pre-Grammys party just the night before: “We’ve had a death in the family,” summarized host LL Cool J, before Jennifer Hudson paid proper tribute with a heartfelt “I Will Always Love You” cover. 

A million critical comments about how Bruno Mars’ pop smash “Locked Out of Heaven” bore The Police’s distinct musical DNA ended up leading to one of the Grammys’ best mix-and-match collabs. Mars’ opening “Heaven” gave way to Sting joining Bruno’s Smeezingtons band for a run through the reggae-tinted Police classic “Walking on the Moon,” and then Rihanna joined in the fun, along with Damian & Ziggy Marley, to pay tribute to the Marleys’ iconic father. “Ladies and gentlemen, none of this would be possible if it wasn’t for Bob Marley,” Mars said as the group launched into Marley’s classic “Could You Be Loved?” for as good a vibe as has emanated from the Grammys stage this decade. 

By most accounts, Macklemore & Ryan Lewis had a tremendously successful night at the ’14 Grammys, delivering an unforgettable performance of LGBTQ anthem “Same Love” (which included a mass wedding) and winning four of the seven awards they were nominated for. However, each of their wins came at the expensive of critical and underground favorite Kendrick Lamar, who many saw as more deserving of the trophies. To address the controversy, Macklemore Instagrammed a pic of a text he sent Kendrick after the awards, in which he claimed, “I wanted you to win. You should have. It’s weird and it sucks that I robbed you.” The post proved even more polarizing — with Drake calling it “wack as f—“ — and Macklemore & Ryan Lewis’ career has never quite been the same since. 

Six years after he nearly derailed his own career by crashing the stage to protest Taylor Swift’s victory over Beyoncé at the 2009 MTV Video Music Awards, Kanye almost went for round two at the ’15 Grammys, approaching the stage where Beck was accepting his album of the year award for Morning Light (over Beyoncé’s self-titled effort), before stopping himself at the last minute. Debate over the almost-incident still spilled over into the weeks that followed, however, as Beck’s victory — for an album most agreed was far less significant in the music industry than Beyoncé’s game-changing surprise release — forced the Grammys to do some serious soul-searching to figure out how to make their awards fall more closely in line with prevailing trends in modern mainstream music. 

Taylor Swift’s album of the year win for her monstrously successful 2014 album 1989 — making her the first female artist to win multiple AOTY trophies — would’ve been plenty noteworthy on its own. But it was her acceptance speech that left the lingering impression, as she warned burgeoning young artists against “people along the way, who will try to undercut your success or take credit for your accomplishments or your fame” — a pretty obvious shot at Kanye West, who had included Taylor-related lyrics in 2016 album The Life of Pablo about how he “made that bitch famous.” The speech gave extra heat to the once-cooled Kanye/Taylor feud, and Snapchat-gate was just a few months away.

Perhaps no Grammy win in recent years has been more indicative of the steps the Grammys have taken to get younger and hipper in the past years than the triumph of Chance the Rapper in the best new artist category at the ’17 awards. The win was not just a major victory for Chance, a fiercely independent artist who became a superstar before he ever released an official solo album or had a Hot 100 top 40 hit, but for hip-hop and underground culture in general, proving that the barriers that separated old-world success from new-world success in the music industry were finally starting to weaken. 

Though he lost out to Bruno Mars for his two biggest nominations that night – album of the year for his unanimously acclaimed DAMN. and record of the year for its Hot 100-topping lead single “HUMBLE.” — Kendrick Lamar won five trophies and opened the show with the evening’s most electrifying performance. Playing a medley of DAMN. highlights with the most elaborate staging and cinematic presentation of his career to that point, Lamar was also unofficially anointed as the conscience of contemporary popular music via guest appearances by cultural elders U2 and Dave Chappelle. The latter briefly interrupted Lamar’s verbal pyrotechnics to offer the sobering reminder: “The only thing more frightening than watching a Black man be honest in America… is being an honest Black man in America.”

Despite “Rapper’s Delight” having first brought hip-hop to national prominence a full 40 years earlier, we still hadn’t seen a rap song take home either song or record of the year at the Grammys before 2019. That changed at the 61st Grammys with “This Is America,” a fiery, Hot 100-topping single with a controversial, gun violence-themed music video, from rapper Childish Gambino (aka TV and film star Donald Glover). The song took home both song and record of the year honors (along with two other trophies), making it a huge Grammy night for both Gambino and hip-hop — though Glover wasn’t even in attendance at the event, with co-producer Ludwig Göransson accepting record of the year in his absence.

At long last, Christopher Cross had to make room in the Grammy history books for another name alongside his: Billie Eilish, the alt-pop phenom who matched his 1981 accomplishment by sweeping the Grammys’ Big Four categories –  best new artist, album of the year (for breakout debut LP When We All Fall Asleep, Where Do We Go?) and song and record of the year (both for hit single “Bad Guy”). Eilish and brother Finneas O’Connell (who shared each of her non-BNA awards as a co-writer/producer), a combined 40 years old at the time of the awards, became increasingly bashful throughout their many podium appearances – accepting record of the year with a mere “thank you… bye!”  

While the 2020 Grammys went down just before the world was turned upside down by the COVID-19 pandemic, the 2021 Grammys were still held very much in the shadow of the global shutdown. After being postponed from January to March for health concerns, the show took place with a largely outdoor ceremony that ended up much quieter and more intimate than usual – though the performances still crackled with electricity, thanks to a multi-stage indoor setup that allowed opening performers Harry Styles, Billie Eilish and HAIM to play one after the other, like an audience-less battle of the bands. The show would go back to business as usual the next year, but 2021 marked a rare win for smaller moments on Music’s Biggest Night.  

Korean pop icons BTS claimed the 2021 song of the summer with their 10-week Hot 100 No. 1 “Butter” — and it was still going down smooth by the next April, when the septet brought it to the Grammys. Beginning with a Mission: Impossible-like opening introducing the group’s various members – setting up control-station computers, descending from the ceiling, even flirting with Olivia Rodrigo in the audience – the Bangtan Boys commanded the stage with one of their highest-energy, best choreographed and most triumphant performances on American television to date, feeling like the biggest pop group in the world (which they were). They didn’t win their lone nomination, for best pop duo/group performance, but they still basically won the night.