For music lovers, the annual Grammy Awards is a must-watch. Not only is the Grammys a who's who of musicians and industry pros, but it also serves up cultural moments year after year. The artists performing really lean into their superstar personas; the grandiosity of the venue means that viewers get some spectacular set pieces; and Grammys fashion often makes history in its own right.
Over the years, the Grammys has been the site of history-making performances, like Prince debuting a foot-tapping musical montage and Tina Turner and Beyoncé singing and dancing to "Proud Mary" together. Iconic Grammys moments can be as unexpected as they are delightful, from Annie Lennox performing in drag to attendees being married by Queen Latifah. The capacity for shock and awe is extremely high, in other words, and each of these moments left us appropriately speechless.
Below, the best-ever moments from in Grammys history.
We Still Had a COVID Ceremony
All award ceremonies in 2021 were complicated by the COVID-19 pandemic: Should organizations even have them? What should the protocols be? When the time came, the Grammys that year was held mostly outside, partially remote, and with fewer guests. It was an impressive feat of coordination.
Alicia Keys Plays Two Pianos
Alicia Keys is never a bad live performer. Period. But she reached even higher heights in 2019. While onstage, she explained that she's always wanted to play two pianos. She then proceeded to do exactly that, in absolutely epic fashion, for a montage called "Songs I Wish I Wrote."
Doja Cat and SZA (Almost Miss Their) Win
When Doja Cat and SZA won for best pop duo/group performance in 2021, it was a comedy of errors. SZA had to be helped onstage because she was on crutches (explaining later she'd fallen out of bed)...and Doja Cat had been in the bathroom and had to come running out.
2023's Rap Extravaganza
The 50th anniversary of hip-hop led to one of the best moments from the 2023 ceremony; Dr. Dre won the first Dr. Dre Global Impact Award, and then musical icons took to the stage for nearly 10 minutes, including Missy Elliott, Salt-N-Pepa, LL Cool J, Flavor Flav, and more.
Beyoncé Makes History
In 2023, Beyoncé won her 23rd Grammy, giving her the all-time record of wins for any artist (fans still noting with irritation she hadn't yet won album of the year). "Thank you so much," she said in her speech. "I'm trying not to be too emotional. I'm trying to just receive this night. I want to thank God for protecting me. Thank you, God."
Taylor Swift's Surprise
Taylor Swift used her 2024 Grammys win (for best pop vocal album) to drop a huge secret. "I've been keeping [it] from you for the past two years...my brand new album comes out April 29. It's called The Tortured Poets Department. I'm gonna go and post the cover right now backstage."
Miley Cyrus Has a Great Night
At the 2024 awards, Miley Cyrus finally won her first two Grammys for her hit song "Flowers." She showed up, looking amazing in Dolly Parton hair—one of our all-time favorite Grammys beauty moments—and subsequently gave an iconic performance. She even changed the lyrics: "Started to cry, then remembered…I just won my first GRAMMY!"
Kristen Wiig as Sia
Sia really understands the power of performance and pageantry, including having incredibly dancers like Maddie Ziegler as her wigged stand-in. But she really upped the ante in 2015: while she sang facing away from the audience, Ziegler and Kristen Wiig delivered a wild interpretive dance.
Adele Praises Beyoncé
It's not abnormal for performers to acknowledge their fellow nominees and artists in their acceptance speeches. It's entirely something else to say, as Adele did in her 2017 speech for album of the year, "I'm very humbled and I'm very grateful and gracious, but my artist of my life is Beyoncé and this album to me, the Lemonade album [which was also nominated in the same category], was just so monumental...All us artists here adore you. You are our light!"
Madonna Performs With Gorillaz
Madonna performing with anyone is usually a visual treat, but the fact that Gorillaz are a virtual band meant that their on-stage collaboration to open the 2006 ceremony was strange and fascinating and cool, with the singer "interacting" with the projected characters.
A Bunch of People Got Married
The Grammys in 2014 saw a mass wedding ceremony: 33 couples (gay and straight) stood in the aisles while Queen Latifah legally married them. She was joined onstage by other artists including Madonna and Macklemore, and Katy Perry caught the bouquet!
Cardi B and Megan Thee Stallion Performed
Cardi B and Megan Thee Stallion performed "WAP" in pretty iconic fashion at the 2021 Grammys. It was actually Megan's live debut, and she performed a few songs before Cardi B joined her—looking like a fembot, naturally—for some of their wildest dance moves.
Britney Spears Performs
To date, Britney Spears has only performed once at the Grammys. Her montage, which included "From the Bottom of My Broken Heart" and "...Baby One More Time" featured an epic red jumpsuit, sparkly backup dancers in weird hats, and...robots? It was a feast for the eyes for the always-impressive singer.
Annie Lennox Performs in Drag
Long before gender fluidity (on the red carpet or in performance) was a more understood action, Annie Lennox took to the stage dressed as a man without telling anyone she was going to. It was a silent, but powerful, slap back against her critics disparaging her androgynous style.
Michelle Obama Unexpectedly Appears
During the start of the 2019 Grammys, Alicia Keys suggested she bring out "some of my sisters" to talk about the power of music. Then, a number of icons came onstage: Lady Gaga, Jada Pinkett Smith, Jennifer Lopez, and, in one of the biggest surprise appearances of all time, First Lady Michelle Obama.
Helen Reddy's Speech
"God is a woman" is a much-loved phrase, somewhat in part because of the Ariana Grande song of the same name. But Helen Reddy was saying it many years before—when it was a lot more controversial. In her 1972 award acceptance speech for best female performance, she thanked God, "because she makes everything possible."
There's a Tie
There have actually been more than 30 ties at the Grammys, but the most notable one will probably always be the tie between Barbra Streisand and Debby Boone for song of the year, for “Love Theme from A Star Is Born” and “You Light Up My Life,” respectively.
Toni Braxton's Dress
I imagine it would be quite difficult to top Jennifer Lopez's green Versace (also on this list), but Toni Braxton was game to show some skin in 2001. At the time, she said, “I’ve always gone a little risqué with all my other awards. I decided that before I got married and had babies, I’d wear this.”
Prince Performs
When Prince and the Revolution took the stage for the first time in 1985, it was to perform the aptly named “Baby I’m a Star” in a six-minute set that included eight back-to-back splits and a ton of dancing before the singer exited through the crowd. It's largely considered one of the best performances ever.
Taylor Swift's Speech
In 2016, Taylor Swift came up to accept her Grammy for album of the year (for 1989) and said, in part, "As the first woman to win album of the year at the Grammys twice, I want to say to all the young women out there, there are going to be people along the way who will try to undercut your success or take credit for your accomplishments or your fame." That was commonly thought to be a not-subtle retort to Kanye West, FYI.
MIA Performs (While Having Contractions!)
I actually did not know this: not only did M.I.A. perform at the Grammys heavily pregnant, on her due date, but she was also apparently having contractions while she performed. She told EW after the performance, as reported by MTV, "The contractions come and go. My fiancé's got the stopwatch going."
Elton and Eminem Perform
The decision of openly gay musician Elton John and controversial rapper Eminem (some of whose lyrics are homophobic) to perform together in 2001 was a controversial one. But it is an impressive performance that deserves a watch, and the two hugged afterwards.
Jennifer Lopez in That Dress
It's almost cliche to put this dress on the list of best Grammy moments, but it's hard to overstate the impact this outfit, and the singer wearing it, had on our cultural conversation. J. Lo was so effervescent in the cut-to-her-naval gown that red carpet fashion has never been the same.
Beyoncé and Jay-Z Perform 'Drunk in Love'
For her "Drunk in Love" 2014 Grammys performance, Queen Bey took to the stage to deliver a very alluring Flashdance-inspired number before being joined by husband Jay-Z. The performance required censoring, but fans were absolutely drunk in love (and the pair received a standing ovation).
Melissa Etheridge Performs Bald
Melissa Etheridge later admitted that she was extremely weak from breast cancer treatment and barely able to move around during this 2005 performance (a tribute to Janis Joplin). "I wanted to show people that no, I’ve been through hell, yeah, this is awful, but I am not dying."
Lady Gaga in an Egg
Lady Gaga later told interviewers she spent 72 hours inside the egg that carried her to the Grammys in 2011. “It was time for me to really prepare and think about the meaning of the song and get prepared for the performance,” she apparently told Ryan Seacrest. “I really wanted to be born on stage.”
Pink Flies
By now, if you know anything about the performer Pink, you know that aerial feats are an important part of her modern-day concerts. The Grammys audience of 2010 did not have that context, though, so when she went airborne in a literal sheet, people were as scared as they were impressed.
Lady Marmalade Performs
When singers Lil’ Kim, Christina Aguilera, Pink, and Mya appeared to sing "Lady Marmalade," they were joined by Patti LaBelle (front woman of LaBelle, who first popularized the song). It was incredible musical synergy and a fascinating blending of generations.
Amy Winehouse Wins
After some visa troubles, the late Amy Winehouse was still committed to performing at the 2008 Grammys...which meant she performed live from London even though it was the middle of the night her time. She also won five Grammys, and her look of surprise and joy is unforgettable.
The Whitney Houston Tribute
Whitney Houston died tragically the day before the 2012 Grammys. Thus, the ceremony had an unexpected tribute to the singer, which included Jennifer Hudson singing a stripped-down version of "I Will Always Love You” with piano accompaniment. It was simple, but beautiful and heart-rending.
Beyoncé and Tina Turner Perform
The 50th Grammy Awards in 2008 had to have something special to commemorate—and having Beyoncé and Tina Turner sing “Proud Mary” in matching silver outfits was absolutely the way to do it. The genuine joy and appreciation on both their faces was palpable.
Aretha Franklin Performs Spontaneously
I imagine that performing at the Grammys is an intense, managed, extremely high-stakes experiences. But after Luciano Pavarotti fell ill at the very last minute, Aretha Franklin—complete icon—sang a rendition of “Nessun Dorma” completely off-the-cuff.
