Grammys 2020: 20 Best, Worst, and Most WTF Moments

For a fleeting moment during the 62nd Grammys, Tyler, the Creator remade the geriatric award show in his chaotic pastel image. Dressed in crimson suits like a barbershop quartet, Charlie Wilson and Boyz II Men sang “Earfquake,” while Tyler’s Igor persona writhed and twitched in anticipation, like a kid waiting for his moment in the spotlight. When the time finally came, he put his foot on the show’s neck, and for almost four minutes wouldn’t let up the pressure. Tyler yelped and screamed his way through a performance of “New Magic Wand” like a man possessed. His platinum-blond bob furiously whipped back and forth, the camera shook like an L.A. earthquake, mini-Igors marched down the aisles to join their father onstage, and an Easter-egg-colored suburban cul de sac burned. By the performance’s conclusion, Tyler fell backward into the flaming abyss like a demon being called home. When he finally won his first Grammy for Best Rap Album, it felt like a reprieve from the night’s endless slog. “I don’t know if I’m gonna be up here again, so bear with me,” said Tyler cupping his gold gramophone. If the Grammys are smart, next year he’ll be back as creative director.

It’s not often that an awards show begins with a truly showstopping performance, but from the moment Lizzo stepped on the Grammy stage to conduct an orchestra of women of color on the opening notes of “Cuz I Love You,” she had jaws on the floor. Dressed in a sparkly dress that looked like the night sky, she led the ensemble in a horn-heavy arrangement of the big, brassy ballad that allowed her to dance and wail an Aretha-esque “I don’t know what I’m gonna doooo” before ending the song full-stop. A ballerina took the spotlight, and the music kicked into “Truth Hurts,” with six ballet dancers nodding their heads to “that bitch” before stripping down to leotards with neon lines that looked like something out of Tron. But what made her “own the stage,” as Alicia Keys later said, was when the singer’s famed woodwind Sasha Flute descended from the heavens, and she trilled on it and shouted out the word “period!” Lizzo topped the whole thing off with five words that made the performance a mic-drop for the ages: “Welcome to the Grammys, bitch!”

One can only imagine the behind-the-scenes chaos at the Grammys when the news hit Sunday afternoon that Kobe Bryant and eight other people had died in a helicopter accident in Calabasas California. The ceremony took place at the Staples Center, the basketball arena that Bryant called home for the vast majority of his professional career. Carrying on with the show like nothing had happened would have been unthinkable. The death of Whitney Houston in 2012 gave Grammy organizers at least 24 hours to rework the show. This time around, they had less than half of that. Luckily for them, Boyz II Men were in the house to sing with Tyler, the Creator, and the group  — down to a trio ever since Michael McCary left in 2003 — came out early in the show to sing with host Alicia Keys a somber version of their 1991 hit cover of “It’s So Hard to Say Goodbye to Yesterday” in honor of Bryant. What could have seemed like a thrown-together tribute came off as one of the night’s most affecting moments.

Now a seasoned Grammys host, not to mention recipient, Alicia Keys has fully honed her act as the Academy’s resident sensitive drama teacher. Her perfectly zen, affirmative attitude toward fellow artists has been a godsend to the Academy — especially this year, given the kind of week they’ve been having. She brought that spacey, serene energy to a musical interlude early in the show, set to Lewis Capaldi’s “Someone You Loved,” where she combined offhanded riffs on the night’s nominees (“Jonas Brothers returned/Billie and Finneas/Camila likes Shawn to call her señorita/Ariana went next …”) with lounge-act-worthy couplets (“It’s the Grammys, gonna have a ball/And here’s Alicia Keys to get you through it all”). She did throw a hint of current-events commentary into the mix — “Commander-in-chief impeached/Y’all get out/Bring Cardi B in/Please show these people what to do!” — but Keys was most successful when she kept things nice and corny: ” ‘Cause music changes the world, just like Beethoven said/Old dude in a wig but I still give him some cred.”

Billie Eilish left the Staples Center with five Grammys, locking in the four major categories — Record of the Year, Album of the Year, Best New Artist, and Song of the Year — plus Pop Vocal Album, in a much-deserved sweep. The O’Connell household had a monumental night and the first win for the clan, for Song of the Year, was equal parts endearing and inspiring as Billie and her musical partner, Finneas, tried to encapsulate their excitement. As the trophies piled up, the duo quickly ran out of people to thank and awkwardly stood on stage, doing their best to fill their allotted time. When Billie’s debut, When We All Fall Asleep, Where Do We Go? was announced as the Record of the Year winner, and the young star walked back out onto a stage she’d left only moments before, she appeared joyful but a little dazed. Given the kind of night she’d had, you could hardly blame her.

Blake Shelton and Gwen Stefani’s live debut of their duet “Nobody But You,” gave us bedroom vibes for all the wrong reasons. One big snooze, it lacked any of the electric chemistry you might expect from a couple who’ve been publicly dating for the past five years — even if they did take the stage dressed as if they were ready for a spontaneous wedding, with Gwen in a gown and Blake in a three-piece suit. The biggest mystery though? Why good ol’ boy Shelton decided to trade his suit pants for denim immediately afterward.

It wasn’t Carpool Karaoke as much as it was diorama karaoke. With its “who’s next?” gathering, set in a kind of rotating house, the all-star roundup during Lil Nas X’s performance perfectly reflected the way “Old Town Road” became everyone’s favorite hip-hop hoedown last summer. In one “room,” BTS; in another, Diplo, his banjo (?), and teen yodeler Mason Ramsey, with the inevitable Billy Ray Cyrus crashing the party. Knowing full well that he may never have a moment like this again, Lil Nas X himself hammed it up, showing off his bowlegged-rider moves while clad in a sparkly suit. It could’ve been ridiculous, but the sheer joy that emanated from everyone singing along to the year’s most ubiquitous song couldn’t be denied. For all the “serious” collaborations during the night, this one felt the most natural and organic. (Bonus points for the Kobe Bryant jersey in the first “set.”)

Ariana Grande and her Cinderella dress got a prime aisle seat in the front row Sunday, but everyone was trying to figure out the identity of the mystery man with the skeleton face paint seated just a few rows behind. (As one Twitter user joked, “Nothing makes you feel old like watching the Grammys, saying things like: ‘Who’s that?’ ‘What the hell is he wearing?’ ‘Do they even make rock n roll anymore’ and ‘is that a skeleton in the audience?'”) Mystery solved: The guy behind the mask was Prince Nasir Dean, the 19-year-old son of Swizz Beatz, and Alicia Keys’ stepson. The aspiring DJ and producer, who goes by “Marcato,” posted an Instagram story of himself getting makeup-ready before the show, alongside his half-brother Egypt, whom Beatz and Keys welcomed in 2010. No wonder the kid hardly blinked an eye at the skeletal figure next to him, while everyone at home was doing a double-take.

The fact that a musician as regional, insular, and independent as Nipsey Hussle was given a tribute at this year’s Grammys is a win for an organization with an egregious record when it comes to hip-hop. But after the death of Kobe Bryant earlier in the day, the collected performers had a Herculean task ahead of them — simultaneously honoring two L.A. icons. Even at its most uneven, the medley accomplished its goal. Meek Mill delivered an impassioned intro, rapping, “When we lost you it really put some pain on me/Got me scared to go outside without that thing on me/When everybody went against me you ain’t change on me.” Roddy Ricch, an artist who was mostly unknown to the general populace only a year ago, got a chance to honor his late collaborator. DJ Khaled played hype man to John Legend as he sang the chorus to the Nipsey Hussle team-up “Higher,” and YG triumphantly appeared after his arrest on Friday on robbery charges. By the performance’s end, photos of Nipsey and Bryant flanked the stars, showing two West Coast icons gone too soon.

Taken by itself, the three-and-a-half-hour ordeal of the 2020 Grammys was a celebrity extravaganza just like any other year — except this was by no means any other year. Sunday’s show took place after a week of highly bitter, highly public feuding between the Grammys’ parent organization, the Recording Academy, and Deborah Dugan, who was abruptly fired from her CEO post 10 days ago after only a few months on the job. Dugan is alleging serious misconduct within the Academy, including voter fraud, corruption, sexual harassment, and a “boys’ club” attitude; the organization has hit back by accusing Dugan of spreading misinformation and bullying employees.

At Saturday night’s industry-only Clive Davis gala, Diddy called the ongoing controversy within the Recording Academy the “elephant in the room.” But aside from Alicia Key’s brief, vague allusion to it having been a “hell of a week,” at the globally televised Grammy Awards on Sunday night, none of the dozens of celebrities who crossed the stage made mention of any controversy — likely because the show is the tightly controlled project of longtime executive producer Ken Ehrlich, who’s worked with the Academy for decades. The Grammy stage is by far the most public and wide-reaching pulpit for the music industry every year, and the fact that no one took the opportunity to address longstanding issues at the show’s own governing body left us with genuine, lasting disappointment.

If Americans didn’t know La Rosalía before, they sure did after her big Grammys debut Sunday night. The young star, the first-ever singer from Spain to be nominated for Best New Artist, performed her new flamenco song, “Juro Que,” followed by a 2020 update of her platinum song “Malamente,” off her now-Grammy-winning 2018 album, El Mal Querer. Being the Olympic-caliber melisma artiste she is, Rosalía nearly blew the roof off the Staples Center with her supple, vocal acrobatics, outsinging every last one of the night’s sad-sap balladeers. She donned a most memorable white fringe jumpsuit with sport chaps (yes, sport chaps), while commanding a unit of male backup dancers in blood-red athleisure wear. Rosalía may have been the only Spanish-language artist to be nominated in a Big Four category this year — beating out Latino chart-toppers like Bad Bunny and J Balvin. But if the Hispanic corner of the industry needed a mainstream ambassador this Grammys season, she made for one killer representative.

Monday’s three-and-a-half-hour Grammy telecast ended up feeling a lot longer this year thanks to a baffling choice: Countless artists trotted out their slowest, saddest songs of the year. There’s nothing wrong with ballads — Demi Lovato showcased a particularly poignant one — but making Billie Eilish perform “When the Party’s Over” over “Bad Guy” as a follow-up to three other piano-heavy performances was perhaps the show’s biggest misfire.

Grammy week was supposed to be a triumphant time for Aerosmith, but the band’s 50th-anniversary victory lap turned into a complete fiasco when drummer Joey Kramer went public with charges that they weren’t letting him back into the band to perform at their own MusiCares tribute show and the telecast itself. He tried to make a judge force them to reverse the decision and even released a video showing himself being turned away from the group’s rehearsal space. This was all because the band felt his playing wasn’t up to snuff. But it’s hard to imagine their shaky Grammy performance going any worse with Kramer behind the kit where he belonged. Also, the intro to Run-DMC’s “Walk This Way” was originally built around a loop of his drum part. Not letting him up there to play it was just outrageously insulting and incredibly unnecessary.

Aerosmith’s Joey Kramer-less performance turned out to be a rough ride: “Livin’ on the Edge” was messy from the start, with Joe Perry producing a wall of overdistorted noise from his guitar as vague protest scenes played on a screen behind them. Then, during “Walk This Way,” when the band stopped playing and Tyler asked, “What’s happening?” it was easy to believe the performance really did fall apart. But instead, Run-DMC busted through a fake brick wall to take us through the 1986 duet that we’ve seen so many times before. Only this time, any sort of skillful give-and-take was gone, as the performers all shouted over each other, verse after verse. It is fun seeing Steven Tyler still having so much fun onstage (not to mention Brad Whitford taking on a Garth Hudson look), but Kramer should be glad he sat this one out.

With the Grammys’ all-star tribute to Prince in the works for Tuesday night, the show’s producers had to find the right performer who could tease it and get people to tune in. They found that person in Usher, who performed alongside Sheila E., beating on her stand-up drum kit, and FKA Twigs performing dirty dances that probably raised the eyebrows of CBS’ censors. Even though Usher opted to wear baby-blue and not purple, he sang a searing “Little Red Corvette,” and during “When Doves Cry” did the splits while FKA Twigs twirled on a stripper pole. But Usher truly channeled the Purple One with a fiery performance of “Kiss,” which found him screaming and dancing on tippy-toes for the front row. He perfectly embodied Prince’s electrifying spirit.

In a year when the Grammys’ treatment of women is under more scrutiny than ever, after the Recording Academy ousted its first female president, the show’s organizers didn’t offer FKA Twigs a microphone for the Prince tribute. There was no explanation for the silent treatment onstage, and she danced like a pro, but each time she got closer to the mic, you just wanted her to share it with Usher and show how Prince inspired her. In the press room later, Sheila E. suggested that FKA Twigs declined to sing, but Twigs tweeted that she had not even been asked. (While we’re at it, we would have also liked to hear Sheila E. sing “The Glamourous Life” or any of the other songs she worked on with His Royal Badness.) Considering the way Prince loved discovering new female talent and putting artists on a pedestal, the fact that she didn’t sing was especially perplexing.

In a night filled with one piano ballad after another, H.E.R. put a new spin on things in the middle of her soulful new song, “Sometimes,” by standing up, picking up an electric guitar, and playing the night’s most memorable six-string solo. The tune was already a moving number about wanting to change for the better — but she improved it by showing just how that’s done with her rousing instrumental break.

When Bonnie Raitt walked onstage to honor John Prine with her gut-wrenching cover of “Angel From Montgomery,” the night started looking up. Here, finally, was a break from the endless parade of pop torch songs and insanely large dresses that stressed us out just from looking at them. It was simply Raitt doing what she does best: strumming the song’s opening on her acoustic guitar in the same beautiful way she’s done it for the past 46 years. But after only a little more than a minute, she stopped. She had only gotten through the first verse — with that incredible, poignant line about being an old woman named after her mother — when she started praising Prine for his Lifetime Achievement Award. Prine may have been wearing sunglasses, but he also looked mildly confused, wondering why this Americana queen was cut so short. We didn’t even get to the part where she reminisces about her rambling cowboy, a line that would have floored Lil Nas X.

This wasn’t the first time that Tanya Tucker sang “Bring My Flowers Now” with Brandi Carlile — they performed it twice during Carlile’s recent Nashville residency — but that didn’t make the pair’s Grammy collab any less special. In fact, it was even more poignant in light of the death of Kobe Bryant earlier in the day. “We all think we’ve got the time until we don’t,” sang Tucker in the Best Country Song winner about celebrating your loved ones while they’re still around. Dressed in an embroidered Western suit and backed by Carlile on piano, the 61-year-old was all gravitas and grace, proving she’s learned more than a thing or two about poise since launching her career at 13.

You couldn’t ask for a more bizarre and uncalled-for Grammys twist than John Legend appearing deep into the telecast and introducing a tribute performance for the show’s long-standing producer, Ken Ehrlich, who retires this year. Cyndi Lauper, Camila Cabello, Common, the War and Treaty, Dear Evan Hansen’s Ben Platt, dancer Misty Copeland, violinist Joshua Bell, pianist Lang Lang, and the original cast of Fame delivered an ensemble performance of that show’s “I Sing the Body Electric” that can only be described as borderline Grammys propaganda … at the Grammys. Shout-out to those onscreen trivia annotations.