My 40 Favorite Music Videos of All Time (Part 3)

10 highlights from the 2000s.

At the dawn of the 2000s, music videos were in a fascinating transition period.

The meteoric rise in internet usage heralded a shift in production and direction techniques, embracing grittier, lo-fi aesthetics fueled by early digital camera adoption. Artists also pushed the envelope even harder, with more videos getting banned from TV airwaves for sexuality, nudity, and, in Robbie Williams’ case, Satanism.

Music video budgets also climbed into eye-watering territory, with directors like Hype Williams, Joseph Kahn, and even Fred Durst (lol) helming multi-million dollar shoots. I don’t know if you could categorically say that music video quality increased across the board, but it meant more visual ideas left a more lasting impression.

In this post, I’ll share my thoughts on my 10 favorite music videos from the 2000s. It’s part of an ongoing series where I highlight my 40 favorite music videos of all time. If you want to travel further back in time with me, check out my salutes to 80s and 90s videos.

Also, don’t forget to like, subscribe, share, and all that good stuff.

---

Let’s go:

21. "Weapon of Choice" – Fatboy Slim (2001)

It’s the most straightforward sales job in the world.

Christopher Walken, a trained dancer, strutting his stuff around an empty hotel. Oh, and at one point, he starts to fly around. Eventually, he sits back down. You don’t get a cleaner creative slam dunk than that.

Interestingly, Walken made the entire endeavor possible by kinda sorta volunteering for the gig.

“He met Spike before he became an actor and he trained as a dancer,” Fatboy Slim said in 2006. “He said to Spike, ‘I would love to get my dancing on film while I’m still young enough to do it.’ So Spike went outside and phoned me and said, ‘Mr. Walken tap-dancing in the video’ and I was like ‘Yes.’”

The rest is music video history. The final cut won the trio six MTV Video Music Awards in 2001 and was named as the greatest music video ever by VH1 the following year. Not bad for an idea that started off as a home movie.

22. "Rollout (My Business)" – Ludacris (2001)

Not many rappers had fun with the music video format quite like Ludacris.

From the Popeye forearms in “Get Back” to the semi-animated zaniness in “Stand Up,” the Southern rap legend has at least a half-dozen classic videos to his name. However, none jump off the screen quite like his work on “Rollout (My Business).” Different frame rates, playback speeds, aspect ratios, and compositions within the frame showcase a mastery of the form. There are also rap lyrics gyrating on the screen and Luda transforming into a baby somehow.

“Before the ‘big head’ post effect was there, we didn’t feel like we had a good enough video,” Ludacris told GQ in 2023. The creative team and his label, Def Jam, knew it was good but not great. It didn’t have that extra sizzle. So let that be a lesson to creators: You can save work in the editing process and craft something that, in the rapper’s words, “moved people’s imagination to a whole other place.”

23. "Bad Romance" – Lady Gaga (2008)

You can’t discuss the theatrical side of music videos without spending at least a few minutes with one and only Lady Gaga.

After busting onto the pop scene with early hits like “Just Dance” and “Poker Face,” the visual accompaniments to her songs became a massive part of her appeal. It’s hard to conceive of now, but Gaga video premieres, whether on TV or online, felt like an event. I’d go so far as to say she was the last artist to work that angle so successfully. “Bad Romance” is arguably the most captivating of all her material to close out the decade.

It’s unapologetically strange and, at times, adorably hacky with its product placement (you get a nice medium shot of her branded Beats earbuds at 1:13), both of which add to its charm. It’s also a love letter to classic cinema, nibbling at the edge of everything from Alfred Hitchcock to Blade Runner to Alien. Part of what makes it so rewatchable is going back through and picking out the Easter Eggs one by one.

24. "You Belong With Me" – Taylor Swift (2009)

First off, everything in this screams late-2000s to me. The swoop haircut on the guy, the bad wigs she wears in multiple scenes, and the High School Musical level of earnestness that permeates the entire video. Is it possible that this song was one of (if not the) last moment where a Taylor Swift single could be enjoyed on the merits of the music alone, unencumbered by ex-boyfriend drama and other general cattiness?

Anyway, back to the video. It’s the epitome of the sum being greater than the sum of its parts. It's a cute concept executed with enthusiasm and a light, deft touch. Most importantly, it captures a universal human experience and tells it through instantly recognizable visual storytelling. That’s the magic at the heart of its transcendence.

25. "Hurt" – Johnny Cash (2002)

“I enjoyed doing [the ‘Hurt’ video] very much because I felt we were doing something worthwhile,” Cash said in an interview shortly before his passing—an observation that ranks up there in terms of grave understatements. Since its initial release, I’ve watched this video dozens of times, and despite that sense of familiarity, it still manages to be spellbinding every time.

The backstory, which Rick Rubin details on Lex Friedman’s podcast, only adds to the video’s mystique. You can feel the weight of Cash’s legacy, of a life’s worth of sadness and regret, imbuing the lyrics with a depth of feeling I’ve scarcely encountered elsewhere, in the Man in Black’s catalog or elsewhere.

That cut from him singing the line, “Everyone I know goes away/In the end,” to the picture hanging on the wall gets me every time. This one’s a true powerhouse.

26. "99 Problems" – Jay-Z (2003)

Speaking of Rubin collabs, let’s talk about “99 Problems.”

Directed by Mark Romanek, it’s a gritty, energetic homage to Jay-Z’s roots. Many of the video’s scenes were filmed near his childhood home, The Marcy Houses in Bedford Stuyvesant. At the time, this record was also supposed to be Jay’s last, context that shaped the short film’s autobiographical nature and the lens through which various aspects of his life are viewed.

For example, watch how the tone shifts subtly and slowly, almost frame by frame, from a breezier, more community-oriented tone to one that’s much bleaker. Along the way, he doesn’t pull any punches with the visuals, grappling with police brutality, mass incarceration, and other realities he dealt with before becoming one of rap’s biggest stars. I suspect many of his contemporaries weren’t as fortunate.

27. "Come Into My World" – Kylie Minogue (2002)

Sometimes, you’ve got to tip your hat to gimmicks that work this well.

Shot in one day in a Paris suburb and directed by the legendary Michel Gondry, “Come Into My World” leans on a repetition technique that wasn’t necessarily new. In fact, Gondry had done another version of this idea for the Chemical Brothers’ “Star Guitar” music video, though not at this elaborate scale. Hey, if it ain’t broke, don’t fix it.

By the time that fifth Kylie Minogue clone emerges right before the video ends, I realized that, despite not having watched it in its entirety in several years before this write-up, I hadn’t moved a muscle after clicking “Play.” I knew what was coming, I knew more or less how everything was pulled off technically, and yet I was mesmerized all over again.

If that’s not proof positive of Pitchfork calling this video “arguably the most rewatchable” of the decade, I don’t know what is.

28. "Honey" – Erykah Badu (2008)

An ode to Badu’s eclecticism as an artist, the “Honey” music video is slept on by too many of these “best of” lists I read before coming up with my own. Everything about the visuals, from the local record store setting to the quirky, often hilarious reimaging of classic album cover art, is a tribute to Badu’s influences and the far-reaching impact of black music on popular culture.

For those keeping score at home, some of the famous album covers she interpolates in the video include:

• Maggot Brain by Funkadelic

• Paid in Full by Eric B. & Rakim

• 3 Feet High and Rising by De La Soul

• Illmatic by Nas

• Let It Be by the Beatles

Sit back, relax, and enjoy the nostalgia hit.

29. "Get Ur Freak On" – Missy Elliott (2001)

Picking just one favorite Missy Elliott music video was a challenging task. Her ability to create distinctive, often surreal images that perfectly complement her music is unmatched in the hip-hop lexicon. But, of all those timeless audiovisual marriages, “Get Ur Freak On” is the video that tops my list.

The retrofuturist vibes are impeccable, with an industrial jungle setting (if that makes any sense) that feeds off the bhangra-meets-sci-fi production from Timbaland. Also, in case there’s any notion that Elliott isn’t the master of her creative domain, here’s what the video’s director, Dave Myers, told Fortune in 2019:

“She reached out to take me to dinner and then took me to see Crouching Tiger Hidden Dragon. We just vibed about perspectives of the world and weird stuff and developed a trust […] There are no limits with Missy. The crazier, the better.”

The last sentence could also describe her music’s appeal more generally.

30. "Stan" – Eminem ft. Dido

Let’s cap this portion of my list off with a throwback to a time that seems like ancient history: When Eminem was routinely put on a pedestal as the best rapper alive.

Regardless of what you think of his late-period work (spoiler: I think it’s 90% mediocre), there’s no denying how evocative “Stan” is as a piece of writing. To that end, a literal interpretation of the lyrics could’ve gone south quickly, especially considering the first choice for the lead role was Macauley Culkin. Against tall artistic odds, co-directors Dr. Dre and Philip Atwell pull it off.

From the muted color palette to the exquisite lightning choices throughout, this music video gets under your skin as much, if not more than the song itself. It subtly echoes the stark aesthetics of 90s-era thrillers like Silence of the Lambs and Seven, ramping up the dread and apprehension as the narrative hurtles towards is shattering climax.

---

Which of these videos are your favorites? Which classic from the 2000s did I leave off the list that merits a spot? Sound off in the comments section.