Last Sunday, Kendrick Lamar won big at the Grammys — five awards for Not Like Us, including Best Music Video, directed by Dave Free and Lamar himself. But the rapper is no stranger to the category: he had already won it back in 2018 for Humble, a song that’s part of his 2017 Pulitzer-winning album, Damn., directed by The Little Homies and Dave Meyers. As all-things-video gain more and more relevance in today’s world, we thought it would be fun to take a look back at the latest twenty-five winners of the Grammy category and rank our favourite ten. So please, join us in this trip down memory lane to remember some of the most emblematic, shocking, beautiful, forward-thinking, and visually striking music videos of the 21st century (so far).
2025: Kendrick Lamar – Not Like Us
Ok, this isn’t nostalgic, but it’s the most relevant since it’s the latest. This mega hit where Kendrick disses Drake has been a topic of conversation this past year — and rightfully so. The music video is highly celebratory, showing a tight community being happy and proud — dancing, smiling, getting together, and just having fun.
2000: Korn – Freak On a Leash
People were so excited – and a bit scared – when we hit the new millennium: technology was booming and some of humankind’s wildest dreams seemed easily reachable. Artists reflected that on their music videos, and Korn’s Freak On a Leash, which won the Grammy in 2000, further proves that. The video, directed by Todd McFarlane (creator of Venom and Spawn, among others), bridges a digital, illustrated world with our bone-and-flesh reality, and plays a lot with special effects (especially of a bullet that’s the common thread in the video, probably inspired by The Matrix, which was released that same year).
2002: Fatboy Slim ft. Bootsy Collins – Weapon of Choice
Decades before the viral Kenzo fashion film from 2016, Spike Jonze was already making people dance in empty yet impressive locations. In 2001, he took legendary actor Christopher Walken (Dune: Part Two, The Dead Zone, Pulp Fiction) to the lobby of the Marriott Hotel in Los Angeles and made him prove his background as a dancer in musical theatre — which earned Walken ann MTV Moonmen award for Best Choreography. Wild, careless, and incredibly cool, it’s still one of the best videos of the century — which the Grammys awarded in 2002.
2003: Eminem – Without Me
It wouldn’t be a proper article about the 2000s without mentioning Eminem, one of the most prolific and awarded artists of the past two decades. In 2003, the music video for his biggest hit to date, Without Me, directed by Joseph Kahn, won big at the Grammys — and looking back at it, it’s easy to understand why. Eminem and Dr. Dre mocked Batman and Robin, there were cameos by porn star Jenna Jameson and TV fitness presenter Kiana Tom, and everything felt like a fever dream. Just brilliant.
2006: Missy Elliott – Lose Control (feat. Ciara & Fat Man Scoop)
“Music make you lose control, music make you lose control.” The iconic opening, paired with the stunning visuals of a group of lined-up dancers in blue hoodies, white gloves, and adidas sneakers, is one of the reasons why Missy Elliott’s Lose Control music video won the Grammy in 2006. With a high-energy choreography throughout the whole song, and of course featuring Ciara and Fat Man Scoop, and even a cameo by Tommy Lee, the video directed by Dave Meyers was also nominated in six categories at the MTV Music Video Awards.
2009: Weezer – Pork and Beans
If you experienced the first days and years of YouTube, before everything became professional and too calculated, you’ll probably remember this iconic music video by Weezer that earned the Grammy in 2009. Directed by Mathew Cullen and released in May of 2008, it features many internet phenomena and YouTube celebrities, who joined forces with the band to create this now historic audiovisual piece — including Mark Allen Hicks (the ‘Afro Ninja’), Cara Cunningham (‘Leave Britney alone’), Caitlin Upton ('Miss South Carolina’), Tay Zonday (‘Chocolate Rain’) or Gary Brolsma (‘Numa Numa’).
2011: Lady Gaga – Bad Romance
At just twenty-five years old, back in November of 2009, Lady Gaga released the groundbreaking music video of Bad Romance, one of her biggest songs to date. It broke the record of becoming the first-ever YouTube video to reach two hundred million views, and it became ingrained in people’s minds — especially if you were a teenage back then like me. Directed by Francis Lawrence, the music video is still iconic today — the Alexander McQueen looks, the choreography, the conversation surrounding beauty or mental health, etc. In 2011, the Recording Academy crowned it as the Best Music Video (and rightfully so).
2013: Rihanna – We Found Love ft. Calvin Harris
It was the peak era of Tumblr when this music video, directed by Melina Matsoukas, came out — and we all made sure to share the GIFs and photos of We Found Love on our social media. It felt more like a short film than a music video, especially thanks to the opening monologue by model Agyness Deyn speaking about a toxic relationship: “It’s like you’re screaming but no one can hear. You almost feel ashamed that someone could be that important, that without them, you feel like nothing. No one will ever understand how much it hurts.” Skating together, smoking weed, making love, taking drugs, and having fun — the most romanticised portray of youth that won the Grammy (and the VMA) in 2013.
2017: Beyoncé – Formation
The most awarded artist in Grammy history collected one statue in 2017 for Formation, a music video directed by Melina Matsoukas (which also won in six categories at the 2016 MTV Music Video Awards). Who doesn’t remember the memorable clip of a fully-braided Beyoncé sticking out of a vintage car, or her standing in front of a house with a bolero hat while nodding up and down? Using historical references and bridging them with more contemporary shots, Queen B served choreography, face, styling, and power.
2019: Childish Gambino – This Is America
Crazy dance moves and a scathing critique on the brutality and violence that Black people endure in the United States are the two pillars on which the This Is America music video stands on. Unfortunately, the song’s message is just as important (or even more) today than it was back in 2018, when it came out — it won the Grammy in 2019. Directed by Hiro Murai, and recorded almost entirely as a single shot, this is one of Childish Gambino’s biggest hits because of its sincerity and reflection on society.