Over the years, the Grammy Awards have been a platform for memorable moments that have left us wondering, laughing, or sometimes screaming in shock, in addition to being a celebration of musical greatness. The Grammys are a must-watch for more than just the music because of these legendary and surreal moments, which range from breathtaking performances to surprising onstage antics.
1. Chappell Roan Called Out Music Labels – 2025
“I told myself if I ever won a Grammy and I got to stand up here in front of the most powerful people in music, I would demand that labels and the industry profiting millions of dollars off of artists would offer a livable wage, and healthcare especially, to developing artists,” new artist, Chappell, said after winning the Grammy for Best New Artist.
2. Taylor Swift Kissed Sabrina Carpenter – 2025
At the Grammy Awards, Taylor Swift kisses Sabrina Carpenter to end suspicions of animosity. Carpenter opened for Swift’s Eras Tour, performing with her on stage in Latin America, Asia, and Australia
3. Alicia Keys Speech – 2025
Keys received the “Dr. Dre Global Impact Award” and shared a powerful message: “This is not the time to shut down the diversity of voices we’ve seen on this stage,” she said. “DEI is not a threat, it’s a gift. And the more voices, the more powerful the sound. When destructive forces try to burn us down, we rise from the ashes like a phoenix, and as you see tonight, music is the unstoppable language that connects us all.”
4. Miley Cyrus Looked Just Like her Mom – 2024
Cyrus had a victorious night with two wins, and she brought along Tish and her sister Brandi as dates. When the former The Voice Coach (Seasons 11 and 13) attended the ceremony, her gorgeous mother, Tish Cyrus, came along to support her daughter, in addition to her 36-year-old sister, Brandi Cyrus. And it was hard to ignore the resemblance between all three.
5. Eminem & Elton John, 2001
Jaws dropped when this unlikely duo took the stage to perform together for the Grammy Awards. And it was a bit more surprising once you realize that their performance spawned a friendship that has endured over the years. Both musicians have said that they bonded over their shared sobriety.
6. 50 Cent & Evanescence, 2004
After the rock band beat the rapper in the “Best New Artist” category, 50 Cent took to the stage during the band’s speech, which confused the entire audience. He smoothly walked back down to his seat moments later to a round of applause and was even given a shout-out from the band.
7. Lady Gaga, 2011
The Star Is Born actress had a truly out-of-this-world experience when she arrived on the red carpet in an egg pod. Models in gold ensembles lifted the vessel through the hordes of people to the stage area, where she crawled to perform.
8. Taylor Swift Wore a Ruby ‘T’ Charm
Swift wore a tiny, dangling T along with her red dress, which sparked speculation from interviewers about whether it stood for Taylor or Travis Kelce. Her boyfriend plays for the Kansas City Chiefs and red is one of the team’s colors.
9. Beck & Kanye West, 2015
After the rapper interrupted Taylor Swift at the MTV Video Music Awards in 2009, he got a lot of criticism. Perhaps this is why he changed his mind when he went onstage to take the mic out of “Album of the Year” winner Beck. Beck welcomed Kanye to speak his mind, but the rapper simply returned to his seat as people looked on in shock.
10. Beyoncé, 2017
It was a sight to behold when the TEXAS HOLD ‘EM performer ascended the stage in a shimmering gold dress and crown. At that time, she was pregnant with twins Sir and Rumi she danced and sang to Sandcastles and Love Drought. While all performances by Queen B are amazing, this one is definitely one of her most memorable.
11. Adele, 2017
George Michael’s death hit close to home for the talented singer, who got choked up during her tribute to the late singer. As she began to sing his song Fastlove she asked to start over even though the show was being broadcast live. “I’m sorry for swearing and I’m sorry for starting again,” Adele said. “Can we please start it again?
12. Michelle Obama, 2019
The audience was taken aback when host Alicia Keys brought several well-known women on the stage, including the former first lady, to kick off the performance.
13. Demi Lovato, 2020
Demi Lovato performed a strong rendition of Anyone, her first live vocal performance since her hospitalization, at the 2020 Grammy Awards, nearly two years after suffering a near-fatal accident. Lovato had to begin the song anew since the situation was so emotional.
14. Prince and Beyoncé, 2014
Prince and Beyoncé performed together at the ceremony, where they put on an electrifying medley of songs. The performance was one of the most talked-about of the singer’s career.
15. Harry Styles and Taylor Swift, 2023
The Shake It Off singer got back together with her ex at the 2023 Grammys. Taylor immediately rose to offer the former member of One Direction a standing ovation as he won “Best Pop Vocal Album” for Harry’s House.
16. Kendrick Lamar: “Drake, What’s Up?”- 2025
It might appear that Kendrick Lamar’s Grammy sweep was the last straw in his long-running dispute with Drake. Fans of Drake must have been uncomfortable when the Compton rapper, dressed in denim-on-denim, which is considered the Canadian tuxedo, took up the golden gramophones.
17. Trevor Noah’s Mispronunciation Of “Hawk Tuah” – 2025
When Trevor Noah mispronounced “Hawk Tuah” during the glitzy award show, internet users were perplexed. One person questioned, “Why did Trevor Noah say hawk tuah like that?” “Did I just hear Trevor Noah pronounce Hawk Tuah “hook twa”?” said another curious user. A third added, “Thank you, Trevor Noah, for forcing me to explain the Hawk Tuah coin to my mother.”
18. Bianca Censori Bared It All – 2025
One of the greatest “uhh… what’s happening?” moments at this year’s awards event was made possible by Bianca Censori’s attire. The only issue with her attire was that it was essentially nonexistent. Beside her husband and rapper Ye, now known as Kanye West, the 30-year-old model wore a fully transparent outfit and completely eschewed her underwear.
19. Jaden Smith Wore Castle On Head
With a huge castle atop his head, the 26-year-old seemed to be the epitome of “living in his own head” as he strolled around the Crypto.com Arena in Los Angeles. It should come as no surprise that Will Smith’s son was mercilessly ridiculed online.
20. Host Keltie Fall On The Red Carpet – 2025
Unfortunately, Keltie Knight, the E! News correspondent, fell on the red carpet in front of the entire world. The reporter was photographed wearing huge Aquazzura platform heels while wearing a silver Atelier Zuhra strapless chainmail gown. She needed a moment to recover from the embarrassing mishap.
21. Babyface Snubbed By Reporters – 2025
Babyface got snubbed at this year’s Grammy Awards in favor of Chappell Roan, and the moment went viral. Midway through an interview with the AP, the Grammy winner was cut off to interview the “Good Luck, Babe” singer.
22. The Weeknd’s Surprise Performance After Grammys Boycott – 2025
The Weeknd and the Grammys don’t appear to be at odds anymore. The singer announced four years ago that he would not be attending the awards ceremony after his 2021 album, After Hours, earned no nominations. Fans were completely taken aback when he took the stage this year because of his forceful remarks and the fact that he had not performed at the previous four Grammys.
23. Will Smith’s Return – 2025
The 56-year-old actor attended the ceremony and paid respect to the late producer Quincy Jones. This was his first time attending the awards show since his notorious “slap”. Some viewers expressed dissatisfaction with his attendance, writing: “Will Smith was not banned from the Oscars, but he was a presenter at the #Grammys.”
24. Charli XCX Underwear Rain – 2025
Sadly, fans were apparently unable to witness the entirety of Charli XCX’s incredible performance at the 2025 Grammys, even though it was pouring underpants onstage. While the stage lights were still flashing and the audience was spotted dancing to her renditions of Von Dutch and Guess, the show reportedly cut to a commercial break.
25. Kacey Musgraves And Lainey Wilson’s “Shady” Reactions – 2025
Beyoncé won a Grammy for a country music song, the first time a Black woman has done so since the Pointer Sisters did it in 1975. The internet clapped its hands together and created a stir after the music history-making moment, attacking fellow category nominee Kacey Musgraves and Lainey Wilson for their “unimpressed” responses.
26. Helen Reddy Proclamation – 1973
Long before Ariana Grande sang “God Is a Woman,” Helen Reddy made that proclamation during her 1973 acceptance speech. Australian singer Reddy won “Best Female Pop Vocal Performance” for her song “I Am Woman” in 1973. The artist and her anthem were symbols of the women’s liberation movement at the time.
27. Annie Lennox’s Mysterious Outfit
Lennox fooled show producers and the audience while dressed in drag in 1984. Lennox was set to perform “Sweet Dreams (Are Made of This),” but the show’s production staff were panicking because they couldn’t find her … because she was unrecognizable while dressed in drag.
28. Frank Sinatra’s Acceptance Speech Was Cut Off – 1994
In 1994, Sinatra’s acceptance speech was cut off early, so Billy Joel paused his performance to purposely waste time. When Sinatra accepted the Legend Award at the 36th Grammy Awards, he gave a tearful yet humorous acceptance speech that was cut short by music. Billy Joel and his choir responded by halting their rendition of “The River of Dreams,” jokingly recognizing the disruption before continuing.
29. Soy Bomb Guy” Crashed Bob Dylan’s Set – 1998
During Dylan’s 1998 “Love Sick” performance, a shirtless backup dancer with “SOY BOMB” painted on his chest interrupted the show, confusing while Dylan remained stoic. The dancer was revealed to be performance artist Michael Portnoy, who later explained that “Soy Bomb” represented a “dense, transformational life explosion.”
30. Wu-Tang Clan Rapper ODB Crashed an Acceptance Speech – 1998
Before Shawn Colvin could take the “Song of the Year” award for “Sunny Came Home,” Wu-Tang Clan’s ODB interrupted, saying Wu-Tang should have won and famously proclaiming, “Wu-Tang is for the children.” Wu-Tang and Puffy had been nominated for “Best Rap Album” in a separate, untelevised category earlier in the night, which caused some confusion.
