Top 20 Grammy Performances of the Century So Far

“44th Annual Grammy Awards” (2002)

“Moulin Rouge!” fever swept across America, and the Grammys were no exception. The all-star collaboration won the Best Pop Collaboration with Vocals award, and the track was already a spectacle before the ceremony. For the night, they delivered an all-out production. Inspired by the song’s sexy and extravagant music video, these divas brought the whole show to a standstill. But the big reveal of special guest and original artist Patti LaBelle ties it all together. The performance came to a shattering crescendo as the vocalists belted their faces off, bringing the entire audience to their feet.

“61st Annual Grammy Awards” (2019)

The 61st annual edition of the awards show boasted appearances by Lady Gaga, Post Malone, and Cardi B. However, after Brandi Carlile took the stage, everyone within earshot was changed. “The Joke” is her anthem to outcasts everywhere. It’s an understated production, considering the other performances that year. With just Carlile and her band framed against the darkness, with the lyrics of her song about being taunted and being outcasts projected behind her in handwritten type. Four minutes of key changes and some face-melting belting later, the rapturous performance had easily become the best of the night.

“63rd Annual Grammy Awards” (2021)

It’s fitting that this showcase of songs from two pandemic albums begins in intimate closeup. As the first awards ceremony after we were all stuck engaging with the world through webcam screens, 2021 was like a welcome return. Taylor Swift starts her medley, featuring the songs “Cardigan” and “August” from “Folklore,” and “Willow” from “Evermore, lying down on a bed of stage grass, delivering right to camera. The camera pulls out to reveal an entire world of forests and trees. Backed by the albums’ co-producers Aaron Dessner and Jack Antonoff, it’s a shockingly stripped down but incredibly powerful presentation.

“60th Annual Grammy Awards” (2018)

When Kesha dropped her first album in five years, it was after her devastating allegations against former producer Dr. Luke had gone public. “Praying” was a stunning and defiant tour de force. The song marked a departure from her uptempo, dance-heavy sound. A nominee for Best Pop Solo Performance at the 60th Grammy Awards, she performed the song with a backing chorus that included other pop superstars. The performance sees them flanking Kesha on either side like her own personal army of angels as she bares her soul through music. It’s one of those moments that feels so much bigger than an award ceremony.

“46th Annual Grammy Awards” (2004)

It should be illegal to have this much talent onstage at one time. Beyoncé had recently departed from Destiny’s Child and was about to win 5 awards for her debut solo album, “Dangerously in Love.” She was so big that she got to perform on the big night twice. Her incredible collaboration with Prince opened the show. The enigmatic rock star may have seemed like an odd pairing for her, but it was a match made in music heaven. Starting with “Purple Rain” and ending with the party anthem, “Let’s Go Crazy,” the two tore up the stage and threw down the gauntlet for everyone who followed them that night.

“49th Annual Grammy Awards” (2007)

Soul and funk superstar James Brown passed away two months before the 49th Grammys ceremony. The Recording Academy tapped Christina Aguilera to honor the man dubbed the “Godfather of Soul.” Emerging from the stage floor in a blinding white suit, she attacked this classic tune with an approach that can only be described as ferocious. Aguilera started standing at the mic in a shroud of white smoke. By the end, she was on her knees, wailing and belting and growling the song’s chorus from the floor of the stage like the second coming of James Brown himself.

“63rd Annual Grammy Awards” (2021)

As the first performer of the main show, the former One Direction member started his pop hit on a slower, groovier note than usual. The arrangement of “Watermelon Sugar” Harry Styles brought to the Grammys emphasized the song’s jazz and funk inspirations, giving his horn section a chance to shine. In a Gucci jacket, no shirt, and a pair of leather pants, Styles proved himself once again to be a consummate showman. Showing off his voice, musicality, and wicked dance moves, the performance got the whole Internet talking. He took home the Grammy for Pop Solo Performance later that night.

“42nd Annual Grammy Awards” (2000)

Talk about production values. Whitney Houston’s appearance at the 2000 Grammys was a five minute showcase of soulful and sultry vocals and turn-of-the-century aesthetics. Featuring some steamy choreography from a troupe of dancers, it’s such a specific moment in time. But one thing that’s timeless is Houston’s talent. She tears through her club classic about a cheating lover before launching into the second song, a Diane Warren-penned ballad. Even more than the killer voice, Houston just looks so effortlessly cool and rich in her two costumes. The whole performance is giving a post-“Matrix,” Y2K aesthetic that’s irresistible.

“64th Annual Grammy Awards” (2022)

The seven-man K-pop boy band made history in 2020 when they became the first Korean group to receive a Grammy nomination. They came back strong at the 2022 ceremony, where they were nominated for their single, “Butter.” The catchy dance pop track gets an espionage-themed performance, with a classy, James Bond-esque concept that sees the band members slinking onto the stage from the crowd. Upbeat, charming, and undeniably smooth, by the time they get to the dance break, the audience is losing their minds at the sheer level of talent. The aura scores are off the charts here.

“53rd Annual Grammy Awards” (2011)

When it’s 2011 and you’re Lady Gaga, you kinda get to do what you want on the Grammys telecast. Doing a song that’s only been released days before the ceremony instead of the one you’re actually nominated for is a strange choice, but it paid off big time. “Born This Way” entered the world with fanfare. Gaga arrived on stage in a cocoon-like vessel, and launched into a high concept number full of her usual artistic flourish. But usual doesn’t mean ordinary here. Surrounded by mannequin heads and writhing dancers, she managed to sing the song, do the demanding choreo, and still manage to deliver a pristine vocal.

“64th Annual Grammy Awards” (2022)


The “Happier Than Ever” singer and her brother and collaborator took advantage of the more intimate, socially-distanced setup of the first few post-COVID ceremonies. Billie Eilish began the song in close-up before the chic set around her was revealed. Then, the room is upside down, flooding with water. She ends the song on top of an upturned house with rain showering the stage. The concept becomes a visual match for the journey of the song, from sweet-sounding twisted love song to a primal scream of resentment. All that would be enough, but the headbanging Eilish is also in rare vocal form here.

“51st Annual Grammy Awards” (2009)


The alt rock legends returned to the Grammy stage in 2009 to perform a song from their nominated album. Radiohead performed “15 Step” with three dozen musicians of the University of Southern California Trojan Marching Band on risers behind them. “15 Step” is already one of the band’s more upbeat songs, if you can call it that. Thom Yorke seems to completely bliss out when he performs it. Adding the youthful energy of the band to the mix made the entire moment feel like a jubilant celebration. The heavy brass and precise percussion is almost entrancing.

“54th Annual Grammy Awards” (2012)

Her sophomore album, “21,” was soaring through the charts with ease. Adele was at the top of the world professionally, but her performance at the 2012 Grammys was anything but smooth sailing. She had undergone a highly publicized surgery on her vocal cords. Her rendition of “Rolling in the Deep” would be her first live performance since recovering. Talk about pressure. Those behind-the-scenes stakes only made her appearance even more triumphant. As soon as she started singing a cappella, it was clear nothing had changed. The audience clapped along as the song built to its first chorus, supporting her all the way. She smashed it. The standing ovation saw some of the industry’s best and brightest cheering her on.

“43rd Annual Grammy Awards” (2001)

Few collaborations have made less sense on paper, and few have worked so well in practice. Eminem’s rap single about an obsessive fan sampled the track “Thank You” by Dido. Elton John sang the chorus at the Grammys instead. The duet has some controversial origins because Eminem had been accused of homophobia due to some of his lyrics. John enthusiastically embraced the singer and his song. Their styles blended surprisingly well, making a statement without distracting from the power of the song. It also gave Eminem’s raw and animated performance style a strangely calm but equally flashy counterpoint.

“47th Annual Grammy Awards” (2005)

Following the devastating Indian Ocean Tsunami in December 2004, a bevy of celebrated musicians came together in tribute to the over 200,000 people who died in the tragedy. Bono, Alicia Keys, Billie Joe Armstrong, and Steven Tyler are just a few members of the impromptu supergroup singing the Beatles hit to inspire donations to the Red Cross. Slash shreds on the guitar. Steven Tyler is on maracas duty. Stevie Wonder brings the house with his harmonica. The star power alone is noteworthy. Clashing styles and genres come together in an explosion of talent for a great cause.

“50th Annual Grammy Awards” (2008)

She rocked the house from an entire ocean away. Nominated for her groundbreaking “Back to Black” album, the English songstress had some trouble getting visa approval to come to the U.S. Instead, the Grammy audience was treated to an intimate show on a nightclub set in London. Winehouse demonstrated her jazz-inspired freedom with the melody and her love of musical improvisation. Performing two tracks from the album, the megahit “Rehab” and the slinky “You Know I’m No Good,” audiences learned she wasn’t interested in recreating tracks as they appear on the album. Instead, they got the authentic, unpolished, and completely original vocal stylings of Amy Winehouse.

“59th Annual Grammy Awards” (2017)

Taking its lead from the iconic visual album the songs appeared on, Beyoncé’s abstract presentation of two tracks from “Lemonade” is a feast for the eyes and ears. It’s unlike anything ever seen on the Grammys stage. Jam-packed with visual Easter eggs and cultural references, half of the performance is spoken word presented against romantic, elegant, and metaphysical scenes. The audience is already hypnotized by the time she gets to “Sandcastles,” the heartbreaking ballad about her husband’s infidelity. That she could convey the message of “Lemonade” so beautifully on a relatively short chunk of time on the Grammy stage is an accomplishment in itself.

“58th Annual Grammy Awards” (2016)

Two years after he and Imagine Dragons burned up the Grammys stage together, Kendrick Lamar returned to set fire to the night. As the most nominated artist of the year, fans had high hopes for Lamar’s performance and he did not disappoint. From the start, the political themes of his work were front and center. Lamar and his dancers entered the set in chains. His band began the performance literally behind bars. The performance was an indictment of racism and the history of oppression against African Americans over the past several hundred years. But the performance is as celebratory as it is incisive, honoring the years of fortitude and perseverance in the face of pain.

“65th Annual Grammy Awards” (2023)

A tribute to an entire genre of music means someone is going to be left out. Roots’ frontman Questlove originally wanted the 50 year anniversary of the hip hop genre to run a half hour, but he was forced down to 14 minutes. Still, the 50 Years of Hip Hop segment on the 65th Grammy Awards was so jam packed with legends that it almost seemed like the list of who wasn’t there was shorter. You know it’s a worthy tribute when you have no idea who could come out next, but each new surprise feels exactly right. Run-DMC, Salt-N-Pepa, Queen Latifah, Busta Rhymes, Nelly, Missy Elliott, and more came together on one stage to honor half a century of groundbreaking, boundary-pushing music.


What was the best performance you ever saw on the Grammys? Sound off in the comments.