The Most Important Grammy Performances Since 2000

Written by Tyler Huckabee • Illustrations by Chaz Russo

F or the most part, the Grammys spend a lot of time droning on about how much music “matters” and why it’s so important and what it all means. This results in a decent amount of painfully stilted monologues and a few predictably safe tributes to the recently departed.

It’s nice, but it’s generally forgettable. How many last year’s 23 (twenty-three!) Grammy performances can you actually remember now? Nobody needs to be reminded that music can be powerful. The Grammys’ ongoing insistence can occasionally smack of desperation.

In light of that, it’s refreshing when a Grammy performance manages to transcend the evening’s pageantry to become less about how powerful music can be and just be a powerful music moment. Last Monday, Kendrick Lamar delivered one of the most astonishing performances in Grammy history. It was bold, substantive, technically proficient, visually dazzling and sonically perfect, and it further cemented his reputation as one of live music’s most dependable bets.

And it got us thinking, what are the other truly great, important performances in Grammy history? Here’s the most important Grammy performance of every years since 2000.



In 2004, Speakerboxx/The Love Below became the first rap album in history to win album of the year, and Outkast removed all doubt that they’d earned the honor via a blistering performance of “Hey Ya,” which is about as perfect a song as you could ever hope to hear. But even that performance was no match for the show’s opener: An astonishing, whirlwind of Prince cartwheeling through his greatest hits, flanked by Beyonce, one of the few people who can keep up with him. In 2004, Prince’s reputation for being one of the world’s great live entertainers was well-established, and America was just starting to get the sense that Beyonce was going to be around for a while. It was a passing of the torch in some ways. A salute to the past in others. It was magical.



It’s difficult now to remember a time when Kanye West was not an not unjustifiably self-proclaimed rap god, but a scrappy newcomer. In 2005, Kanye was well-known but poorly understood, and his legacy as an icon was far from secure.

Contrary to his current brand, being an underdog serves Kanye well. In 2005, his hunger led him to take risks—like teaming up with John Legend, Mavis Staples, the Blind Boys of Alabama and a church of singing parishioners. It was in turns funny, chilling, inspiring and even transcendent. This was before Kim Kardashian, “Runaway” and “I’mma let you finish…” It was before liking Kanye got a little complicated. In 2005, all you saw was an incredibly rare talent at the absolute height of his game.


Madonna and Gorillaz: “Feel Good, Inc” and “Hung Up”

And if anyone knows about putting up a fictional front on stage, it’s the woman Gorillaz teamed up with at the 2006 Grammys.

Gorillaz are a notoriously tricky act to categorize. Too weird for the mainstream, but too good to not be popular, Damon Albarn and Jamie Hewlett’s creepy-cute quartet of indie/trip-hop/alt-rock purveyors exist only as holograms because it’s a little easier to buy songs like “Feel Good Inc” as the work of a few hipster demons than from actual people.

And if anyone knows about putting up a fictional front on stage, it’s the woman Gorillaz teamed up with at the 2006 Grammys. The Gorillaz holograms were and remain an eerie sight, made all the more so by Madonna’s effortless duet with them. Her then 47-year-old body was at least as astonishing as the technology used to bring the Gorillaz to life, but their collaboration together was a chilling reminder of truths Albarn and Madonna know only too well: the music industry is full of holograms.

Watch Madonna and Gorillaz perform at the 2006 Grammy's on YouTube.


Shakira and Wycleff Jean: “Hips Don’t Lie”

This was 2007. Eight full years after Ricky Martin’s 1999 Grammy performance of “Cup of Life” signaled what was supposed to be the return of latin music to the mainstream. It didn’t really work out—until 2007, when Shakira exploded into the American consciousness with a hearty vibrato, a mess of curls, and the most hypnotic hips in pop music. She was a hurricane, and although Shakira was reportedly suffering from a very rough fever the night of the Grammy’s, you’d never know it to see her gyrating next to Wycleff Jean, who seemed just as astonished at what he was seeing as everyone else was. Can you blame him?

If you stare into Shakira’s hips long enough, will you see the future? It is possible.

While “Hips Don’t Life” is clearly indebted to Bollywood, its ultimate effect on the mainstream was to bring Latin music back in a way few could have possibly predicted. But how could anyone predict someone like Shakira?


Amy Winehouse: “You Know I’m No Good” and “Rehab”

This is cheating a bit, because Winehouse wasn’t even at the Grammys in 2008: her visa wasn’t cleared in time to make the ceremony. But the Grammys get what the Grammys want, and the Grammys wanted the year’s most talked about artist to sing for their show. So Winehouse was livestreamed in from London, ripping her way through “You Know I’m No Good” and “Rehab.”

It’s hard to listen to “Rehab” today without feeling like an asshole. The coy, winking powerhouse of a pop song ended up being a middle finger at the addiction that would soon claim Winehouse’ life, and this, more than anything, is what makes the performance so vital to the past ten years of pop music and has made Winehouse such an indispensable figure over the past decade. Rarely has an artist’s work, life and death all blended together in such tragic harmony. It’s horribly sad now, but in 2008, it was magnetic. She may have been fiddling while Rome burned, but when the music is this good, you couldn’t help but join in.


Radiohead: “15 Steps”

Few bands give less of a damn about the music industry than Radiohead. Never had that been more apparent than in 2009, when In Rainbows dropped online for the price of a song, both anticipating and probably helping create the eventual streaming music boom. They might as well have driven around Los Angeles throwing Molotov cocktails into the homes of Grammy voters.

Still, the Grammys like nothing more than proving they can be good sports about the industry’s odd ducks, and they managed to wrangle Thom Yorke and Co. into their first live televised performance in the U.S. since 2000. With an assist from the USC Trojans Marching Band, the performance captured everything about what made Radiohead such a weird and wonderful gaggle of music geniuses, but the performance is really notable for what it heralded. Radiohead was the first major act to get wise to the coming age of digital music. After In Rainbows, even the Grammys couldn’t deny it.

Watch Radiohead's performance on YouTube.



It’s never been easy to separate Lady Gaga the gonzo performance artist from Lady Gaga the recording artist She is, in some ways, a pop music Marilyn Manson—a genuine talent whose theatrical antics can overwhelm her true gift. That was particularly true in 2010, when her garish getups were splayed across every magazine cover on every supermarket checkout line in America, when she bothered to wear clothes at all.

But if there’s one pop star who had mastered the balance of theatricality and musicianship, it’s Elton John, and his appearance at the 2010 Grammys grounded Gaga. While Lady Gaga opened with the inescapable “Poker Face,” which featured her doing the usual Lady Gaga thing, the performance went to a different stratosphere when Elton John joined her on stage and the two sat down at twin pianos for “Speechless” and “Your Song.” For a lot of Americans, it would be the first time Gaga’s impressive, classically trained voice would become more central than her outfits, and John’s presence was a reassuring reminder that she was not breaking the mold so much as accepting a torch. When you saw the two, beautiful, sparkling weirdos on stage, you couldn’t help but warm up to both of them.



Hey, did you know there was a time when Rihanna was thought of as sort of a demure, girl-next-door type? At the 2011 Grammys, Cee-Lo’s Muppet-backed take on “Forget You” was flashier and Janelle Monae’s “Cold War” was a better performance, but history will remember the the 53rd Grammy Awards’ opener as its true game changer, in which Rihanna emerged as mature, liberated and in control.

This was not a foregone conclusion. Two years earlier, the black eye Chris Brown gave Rihanna had been blasted into the American consciousness, making her an unenviably ubiquitous poster child for domestic abuse. She was seen as a victim. Sympathetic, of course, but in need of rescue. But from the very start of “What’s My Name?” she displayed a newfound ease and confidence. Even Drake, one of the most blindingly charismatic performers of the decade, couldn’t compete. 2011 was the year when Rihanna began her transformation from pop star to icon—from survivor to champion. After all, when was the last time you heard Chris Brown on the radio?



How do you top Paul McCartney, Bruce Springsteen, Dave Grohl and Joe Walsh teaming up for an Abbey Road medley? By being a tribute to the future of music instead of its past. In 2012, the music industry was clinging to Adele like a life raft, since she was (since remains) one of the few musicians completely immune to all the predictions about the death of album sales. She did this by crossing generations and cultural divides, and “Rolling in the Deep” was every bit as popular on Pitchfork as it was NPR. It defied every ounce of conventional wisdom about the state of the modern music industry, and did so the old-fashioned way: good songs and a voice like a god.

It defied every ounce of conventional wisdom about the state of the modern music industry, and did so the old-fashioned way: good songs and a voice like a god.

Then came vocal cord surgery, and those who fret about such things fretted about whether or not or Adele’s voice would ever be back to a hundred percent. Worrying was a waste of time, as it turned out—girl still had the chops—but more importantly, the future seemed to snap into focus when Adele sang. The perfect mix of raw talent, commercial viability, personal charm and refreshing authenticity were apparent from the single phrase “We could have had it all.” Could have?



Justin Timberlake kicked this evening off with Jay-Z and “Suit and Tie,” which didn’t prove anything we didn’t already know about Timberlake’s bonafides. We’ve known Justin Timberlake was a big deal since before he could drive.

Frank Ocean was another story. He’d spent the past few years making waves with the hipster-hip-hop set Odd Future before striking out on his own, but his work there barely hinted at his full potential. Then, in 2012, he published a beautifully written letter in which he said that his first love was with a man. As Pitchfork’s Ryan Dombal said at the time: “Its beautiful ambiguities had people reacting with sensational headlines, and then amending those sensational headlines, and then thinking about how and why they personally reacted to such sensational headlines.” That’s a long way of saying that Frank Ocean is one hell of a writer. When his debut solo effort Channel ORANGE released shortly thereafter, it confirmed all the best suspicions about him.

For all that, when the Grammys landed, Ocean was a relatively unknown musician with only one critically acclaimed album under his sweatband. The Grammys are not known for taking risks on indie upstarts, but they took one on Ocean and instead of using it on “Thinking About You”—the closest thing he had to a hit—he plinked around on a keyboard and crooned the lovely, understated “Forrest Gump.” It was mystifying. It was hypnotic. And it was a rare moment in which star power took second place to genuine emotion.

Watch Kendrick Lamar and Imagine Dragon's performance on YouTube.



Two important things to remember about this performance. First, Kendrick had just lost “rap album of the year” to Macklemore, in one of the most infamous Grammy flubs of the past decade. Second, Imagine Dragons was mostly known as a middle-of-the-road alt-rock act with one popular single to their name. All that to say, expectations were low for this mashup

But this mashup didn’t just work; it astonished. “Plan B is to win your hearts and minds right now,” Kendrick told the audience, before launching into a breathless, searing flow that dropped jaws across the nation and swiftly erased any doubt that Kendrick deserved every word of hype he’d been getting over the past year. His blistering delivery could have overwhelmed Imagine Dragons, but they seemed invigorated by his performance. “Radioactive” sounded downright lit.

The 2014 Grammys had a number of notable moments: Pharrell, Stevie Wonder and Daft Punk teaming up for “Get Lucky.” Macklemore and Ryan Lewis soundtracking a mass same-sex wedding, officiated by Madonna. But those performances are supposed to be good. It was hard to not feel like your strings were being pulled. What made the Kendrick/Imagine Dragons collab work was the immediateness of it. No flashy gimmicks. No iconic legends brought out of retirement. Just sheer, raw force.

Kendrick Lamar and Imagine Dragons


Sam Smith and Mary J. Blige: “Stay With Me”

In 2015, “Stay With Me” was one of those songs you had heard even if you hadn’t really heard it. It was so omnipresent that it was hard to remember a time before it had been part of the cultural conversation. Performing the song was a given for the Grammys, who live for the sort of rags-to-riches tale Sam Smith so easily inhabited, but gigs like this are often so obvious as to be rote. How do you freshen up a song that had been overplayed to the point of sounding like white noise?

The answer: You add one of the most powerful voices of that or any other year. Mary J. Blige was a natural fit for “Stay With Me,” her voice sounding powerfully weary next to Smith’s rich melancholy. It added a new layer of devastation to a song that, before, had sounded simply glum. If it hadn’t been famous before this, this performance would have done the trick.


Kendrick Lamar: “The Blacker the Berry” and “Alright”

As noted, this entire article was inspired by Kendrick’s terrific, socially relevant medley of two songs off 2015’s To Pimp a Butterfly and one unreleased number that closed the performance off like an exclamation point. The visual feast—from the chain gang opener to the African jungle-inspired climax—was something to behold, but pyrotechnic wizardry has yet to conjure anything as mesmerizing as Kendrick’s flow—convicting, thrilling, haunting and inspiring. He was the best reason to watch the Grammys this year, and most others.