“Mirrors” made Justin Timberlake just the second artist to ever win both the video of the year and the Video Vanguard awards in the same night in 2013, an achievement likely more about his overall career momentum at the time than “Mirrors” being a particularly great video. Which isn’t to say it’s bad: Floria Sigismondi gives its split romantic narrative an elegance befitting the stately midtempo ballad, but the pacing of the video never feels right and its multiple timelines never totally cohere into something you want to follow for a full eight and a half minutes.

At the peak of Katy Perry’s pop ostentatiousness, “Firework” could rank as only the second-most-memorable video from the Teenage Dream era with explosive material shooting out of her chest. It’s a solid video with strong intent, but it lacks the gaudy panache that really made the visuals on this album cycle so iconic for Perry, and its straight-faced messaginess can get a little tiresome on repeat viewings.

Green Day spends a lot of time walking that lonely road in “Boulevard of Broken Dreams”… and walking… and walking. Not a lot truly happens in “Boulevard,” as the band traverses desolate landscapes while director Samuel Bayer scratches up the film stock like his name was DJ Premier. It’s effective enough as the hangover back half of a two-parter with the more rambunctious “Holiday” but a bit unremarkable on its own; maybe they should’ve been nominated in tandem.

The arguable centerpiece of the entire 1989 era, “Bad Blood” captures a moment in Taylor Swift’s megapop crossover where everything was about size. And so we not only get an entire fake Joseph Kahn-directed action flick, we get multiple Squads worth of cameos — everyone from Zendaya to Hayley Williams to Ellen Pompeo — as well as a drop-in from the hottest rapper of the time. The spectacle is dazzling, but the actual content is unwieldy; Swift’s blockbuster fantasies were obviously much better served by her own Eras Tour a decade later.

Can’t fault “Lady Marmalade” for lacking star power; no other video of the year winner has even three lead artists to its credit, let alone four topline hitmakers (and a fifth cheering them on from the wings in co-producer Missy Elliott). There’s not a ton to remember about the video beyond the five of them, though; otherwise it’s basically just a more commercial for Moulin Rouge! than any trailer could ever hope to be.

Undoubtedly effective as promo, as the images of Miley’s close-up, tear-stained stare, her sledgehammer-licking and her nude riding of the titular item of destruction all became about as iconic as any pop visuals of the 2010s. Unfortunately, the first one doesn’t really go with the last two, as the video’s jarring vulnerability is undercut, not enhanced, by the provocations of its more salacious imagery — and the presence of the deeply problematic Terry Richardson behind the camera certainly helps little with that part of it.

Swift’s second video of the year winner is a mostly successful spin on the colorful camp aesthetic of Teenage Dream-era Katy Perry — down to Perry herself making a cameo, officially putting to bed any rumors of a lingering feud between the two 2010s superstars. But as “Bad Blood” previously demonstrated, Swift just isn’t at her best going so big and broad; some of the attempts at comedy fall flat and the video’s eye-popping color schemes feel a little visually exhausting by the end.

The surprise top-prize recipient at the 2006 awards, Panic!’s big win for its breakout hit arguably marked the high point of mid-’00s emo’s entire pop culture moment. It wasn’t totally unworthy as a winner, but you really have to be invested in the broad-strokes theatricality of frontman Brendon Urie and his Tim Burton-goes-Moulin Rouge! aesthetic to get much out of it; he’s a captivating carnival barker but there’s not a ton of thrills offered elsewhere in the “Tragedies” circus.

One cannot often fault Abel Tesfaye for not going big enough, but you can’t help but wonder what “Blinding Lights” might have looked like with a late-’90s video budget behind it. As is, The Weeknd is an undoubtedly commanding presence at the bloody-and-bruised center of the video — with a quickly iconic look that soon took him all the way to the Super Bowl — but without a co-star or any particularly memorable set pieces for him to play off of, the action of the song outpaces the action of the visual a little too easily.

Madonna had already built a 15-year resumé as the arguable MTV GOAT by the time she finally won video of the year for “Ray of Light“ in 1998. Her win wasn’t just a belated make-good — the song and the video were a real moment for Madge in their own right, proving she could still thrive at the dawn of the TRL era — but if you were to guess the lone win of her career in the category, “Light” probably wouldn’t be one of your first five guesses. It’s one of her few videos where she feels like she’s playing a supporting role to the (admittedly captivating) photography effects and slice-of-life tableaus.

At the absolute post-grunge peak of ’90s alt-rock, there was perhaps no bigger band on MTV than Aerosmith, whose trio of Alicia Silverstone-starring Get a Grip videos brought Steven Tyler and company to a new peak of popularity a full 20 years into their career. “Cryin’” perhaps holds up the best of the three, as its leading lady’s performance — an intoxicating mix of lip-biting vulnerability and bungee-jumping badassery — gave notice that she was well on her way to becoming an era-defining superstar in her own right.

The first black-and-white video to take home the VMAs’ top prize since 2009 is a sci-fi fantasia with elements of Frankenstein and Poor Things and cameos from Ethan Hawke and Josh Charles. But the most memorable parts of “Fortnight” are the scenes with just Taylor Swift and Post Malone staring at one another, their chemistry easy and obvious, even in the eye of a tornado of unread letters.

It might not be her best-remembered video, but coming at the height of the media scrutiny and often outright cruelty that plagued her life and career in the mid-’00s, the paparazzi-besieged “Piece of Me” played an important part in cementing Spears’ pop star lore and setting her career up for its second decade. Whether the video’s excessively ’00s fashion, styling and tanning adds to or detracts from its iconicity is likely in the eye (or age) of the beholder.

Clearly the “This Note’s for You” video was needed in 1989, when MTV’s first decade culminated in an era of visual excess and explicit commercialization that classic rocker Neil Young was all too happy to take the piss out of. Doesn’t make it OK for Young to have beat Michael Jackson and Madonna for the VMAs’ top prize — a trophy it took the latter another decade to take home, and which the former somehow never won in his lifetime — but the clip remains a fun time capsule and a fascinating anomaly in the awards’ history.

The telenovela-inspired clip for “Havana” took Camila Cabello’s true breakout solo smash to the next level, giving it both greater gravity and more campy fun, while making her look like an unquestionable star. Historically, though, it’s hurt somewhat by emerging from one of the great VMA classes in recent memory, which also included top-level clips from the Carters (Beyoncé and Jay-Z), Childish Gambino, Drake, Ariana Grande and Bruno Mars & Cardi B — all of which were at least as deserving of the big win, and a few arguably moreso.

The video that proved that Lil Nas X would have pop culture resonance well beyond his historic “Old Town Road” moment, “Montero” often teeters on the edge of garish in its bluntly rendered heaven-and-hell landscapes, but remains compelling enough to enrapture fans and enrage haters in equal measure —and ensure a tsunami of content surrounding the song, driving it to immediate-smash status. “Y’all are not gonna win bro,” he tweeted about the latter group when it first mounted the backlash to the song and its video; he may as well also have been talking about the other nominees for video of the year in 2021.

“My Name Is” and its TRL-conquering video made Eminem a star in 1999, but the next year’s”The Real Slim Shady” was the one that guaranteed he was already on his way to icon status. Not all parts of the video have aged brilliantly — good luck explaining to anyone under the age of 35 why a Tom Green mini-parody was really necessary at the time — but the unforgettable shots of Slim directing an army of nodding lookalikes still feel equally thrilling and terrifying a quarter-century later.

One of Swift’s most successful videos at capturing the tenor of the song it accompanies, “Anti–Hero” cleverly reflects the pop superstar’s late-night mania by personifying the different voices in her head with their own Swiftian incarnations. The clip could certainly do without (or at least with a shorter version of) its post-bridge vignette imagining Swift’s descendants fighting over her will, but the closing shot of the multiple Taylors enjoying a drink together on her rooftop is among the most satisfying in her videography.

Sneaking in to steal video of the year in 1999 from the Backstreet Boys, Ricky Martin and KoRn at the very height of the teen-pop, Latin-pop and nu-metal explosions was Ms. Lauryn Hill and her evocative splitscreen clip for Hot 100-topping solo breakout “Doo Wop (That Thing).” The video is less spectacular than those other TRL-era-defining clips, but arguably more effective, with the ’60s and ’90s versions of L Boogie’s performance clip meshing seamlessly to reinforce the idea of “Doo Wop” (and its universally acclaimed parent album, The Miseducation of Lauryn Hill) as immediately timeless.

A gimmicky video that the band would end up immediately resenting — but what a gimmick. “Right Now” brought Van Halen into the ’90s with the kind of socially conscious statement video that would loom large in the decade’s culture, via “Right now…” text captions accompanying rapid-fire scenes portraying societal ills, scientific advancements and general facts of life. The Mark Fenske-directed clip mixes in just enough silly with the serious (“Right now, Mike is thinking about a SOLO project”) to not become overbearing, and… well, the ’90s was kind of a serious time anyway.

Eminem at his absolute pop peak, playing the superhero he’d essentially become to suburban America with the appropriate mix of irreverence, incredulousness and vendetta-settling irascibility. Decades later, the adventures of Em and Dre in “Without Me” were still fondly remembered enough to inspire a sequel in 2024’s “Houdini”; the concept proved ageless enough that it helped the latter match the former’s No. 2 peak on the Hot 100.

Rihanna was already a confirmed hitmaker, but she wasn’t a superstar until she laced up for the many unforgettable looks — the French maid’s outfit, the top hat and one-piece, the silver body paint — of the “Umbrella” video. The clip came at just the right time not only for Rihanna, but for MTV and the VMAs, proving at the cultural low point of the music video format (and possibly for 21st century pop stardom in general) that the right visual could still become instantly iconic.

The final piece of OutKast’s complete cultural takeover of late 2003, the joyous “Hey Ya!” video presented Andre 3000 as a one-man Fab Four, perfectly capable of creating globe-sweeping Andremania with one expertly deployed pop song. It all worked — perhaps a little too well for the artist’s liking — and today stands as an essential Polaroid of OutKast’s ultimately short-lived run at the apex of popular music.

With clever sleight-of-hand, inspired camerawork and some stellar dance moves, Jonathan Glazer’s clip for U.K. acid jazzers Jamiroquai’s future-fearing Stevie Wonder pastiche “Virtual Insanity” briefly made frontman Jay Kay an MTV star. The video’s unexpected win at the VMAs certainly shows an MTV in a sort of transition moment between superstar eras, but its simplicity and lack of special effects means it’s aged much better than most big-budget affairs of the late ’90s.

Before his current 2024-’25 run, it looked like “HUMBLE.” and its video would represent the pop star peak for Kendrick Lamar, standing out from the SoundCloud rap pack like he does in its video as the one visible face among hordes of the faceless nodding masses. It felt like the evolutionary “Real Slim Shady” — and if this year, “Not Like Us” makes Kendrick the first rapper since Eminem to win multiple video of the year trophies, it would be extremely well-deserved.

The VMAs legacy of The Cars’ biggest MTV hit will forever be it winning video of the year over Michael Jackson’s “Thriller.” Undoubtedly a miss, but not as big of one as it could’ve been, considering that “You Might Think” is a perfectly imperfect encapsulation of the freewheeling creativity and visual borderline-anarchy of the channel’s earliest days, with its elastic reality turning frontman Ric Ocasek into a comic book superhero — or supervillain, it’s sorta hard to tell behind those sunglasses.    

Arguably the moment when Taylor Swift officially separated herself from the pack to become a one-of-one icon for the 2020s, “All Too Well” demonstrated that not only could Swift turn a 10-minute re-recording of a decade-old deep cut into a Hot 100-topping smash, but she could make an award-winning short film out of it too. With help from Sadie Sink and Dylan O’Brien, the wistfulness and emotional brutality of the clip matches the song stride for stride, with its mid-song kitchen argument in particular capturing the kind of fight whose actual meaning loses weight almost instantly, but whose impact stays with you decades later.

Nothing says “1980s” quite like those blocky computer-generated everymen, or Straits frontman Mark Knopfler’s neon headbands, for that matter. But it’s the obvious datedness that has made “Money for Nothing” so enduring — down to the still-chuckle-worthy fake MTV video that plays on its in-store TVs — and it remains as essential a slice of mid-‘80s pop culture as you could hope to reheat in your installed microwave oven 30 years later.

The first clip from a Black artist to take home video of the year, “Waterfalls” is perhaps even more heavy-handed with its ‘90s messaging than “Right Now” — and with far more dated special effects — but it’s balanced by the timeless cool of T-Boz, Left Eye and Chili, three all-seeing deities casually shimmying on the water. And the more dramatic parts do still work: No matter how many times you see it, the ghost of the now-slain drug dealer of the first verse (played by ‘90s rapper Shyheim) trying and failing to hug his mother stays a gut-punch.

The mix of live action and animation that defines the first part of “Need You Tonight”/”Mediate” looks a little clumsy today compared to some of its similarly VMA-conquering peers — but what hasn’t aged at all is the all-consuming magnetism of INXS frontman Michael Hutchence, looking well on his way to becoming the Mick Jagger of the MTV era. And the second half’s recreation of Bob Dylan’s “Subterranean Homesick Blues” lyric card-tossing bit is a smart and still-captivating throwback to what many consider to be the first classic music video.

The first woman artist to win video of the year wasn’t Madonna, Janet, Whitney or Mariah, but Sinéad O’Connor, framed in uncomfortable close-up as she sang (and viscerally felt) one of the most wrenching torch songs of the late 20th century. The famous tear scene — as indelible an image as MTV’s second decade produced — wasn’t inspired by the departed lover from the Prince-penned lyrics to “Nothing Compares 2 U,” but O’Connor’s own recently deceased mother, a loss she made the whole world feel during her all-too-brief period of pop stardom.

“The impossible is possible tonight,” frontman Billy Corgan promised on Smashing Pumpkins’ symphonic rock smash, and the Jonathan Dayton- and Valerie Faris-directed music video certainly made you believe it. A spellbinding redo of the classic silent short A Trip to the Moon, “Tonight, Tonight” showcased a scope, an ambition and a sense of romance that most of the Alternative Nation was supposed to be far too cool for, helping to launch the era’s preeminent group of overachievers far past the rest of their ’96 peers.

As confrontational as Beyoncé has gotten as a pop star, with a video that took on Katrina and police shootings and got her Super Bowl performance — which included the song, just a day after the video’s surprise release — boycotted by some unions. The video’s purposefulness was powerful, and so were the shots of a glammed-out Bey ghost-riding the whip, or her commanding a phalanx of male backing dancers in a dark church hat and darker lipstick. She never looked bigger or badder.

For the many cultural failings of the ‘00s as a decade, it did make Missy Elliott MTV’s biggest star for at least one night, as the reality-warping rap icon’s took home video of the year for her greatest pop moment. “Work It” might not have one image as iconic as the garbage bag outfit from “The Rain,” but it wins in sheer volume: Missy the DJ swarmed by bees, Missy the B-girl dancing with the next generation, Missy the icon cool enough to even ignore Prince’s advances.

Just before grunge was about to explode worldwide at the end of 1991, R.E.M. took their bow as American alt-rock’s most-celebrated elder statesmen with the breathtaking and VMAs-dominating “Losing My Religion.” The video turned the band’s most exquisite composition into living, breathing art, and made its once-camera-shy frontman Michael Stipe an absolute MTV superstar, helping set the band that defined underground ethics and aesthetics for the ’80s on the path to signing what was at that point the highest-paying label deal in industry history in the ’90s.

Don Henley’s timeless anthem of lost innocence somehow got a video even more evocative than its lyrics, thanks to fashion photographer-turned-video director Jean-Baptiste Mondino. A barrage of unforgettable black-and-white images from its opening observed-from-afar lovers on the beach to its haunting closing shot of Henley driving down the empty street, “The Boys of Summer” plays like a nostalgic itch you can’t scratch, deep and indelible and forever just out of reach.

“Bad Romance” was the kind of video it should take an artist 5-10 years to build up to; Lady Gaga got there in about 18 months. With its combination of sci-fi imagery, innovative art direction and choreography and sheer superstar presence, “Romance” not only cemented Gaga as a superstar but raised the bar for her entire generation, and reconfirmed that great music videos were still an essential item in the pop star job description.

Nirvana were the leading lights of the ’90s grunge explosion, but Pearl Jam were actually its biggest stars — thanks in no small part to the ineffable power of the “Jeremy” video, a devastating look at the teenage suburban alienation that would quickly become a decade-defining concern. It’s essential three decades later for what it started, but also for what it ended: Pearl Jam didn’t appear in another music video that decade, and “Jeremy” title performer Trevor Wilson quit acting shortly after, before tragically dying in 2017.

Even before Lady Gaga announced that music videos were officially back at the turn of the 2010s, Beyoncé confirmed that they could still be as vital as anything in pop culture. The black-and-white dance clip for “Single Ladies” was a classic video the way they used to make ’em — low-budget and high-energy, with a simple concept executed to perfection and a star performer you couldn’t turn away from if you tried — and proved that going viral in the early days of YouTube could be just as impactful as entering heavy rotation at the dawn of MTV.

In its own way, as much of a standard-setter for ambition and ingenuity in ’80s music video as “Thriller” was — and with a performer who wasn’t even quite a superstar yet to help sell it. “Sledgehammer” certainly got Peter Gabriel the rest of the way there, as Stephen R. Johnson’s clip lent him an otherworldliness by treating his body like silly putty in its array of mind-stretching animations — matching Gabriel’s most limber vocal and (appropriately) hardest-hitting song yet with a video that refused to accept any perceived limitations within its artform.

The dizzying height of both Rihanna’s superstardom and of the EDM era, and still the greatest music video of the entire 21st century a quarter of the way through. Melina Matsoukas’ clip for “We Found Love” doesn’t just match the obvious euphoria of RiRi’s floor-filling Hot 100-topper, it finds a Pantone swatch book’s worth of shades within it — romantic, exhilarating, life-affirming, death-defying, perception-altering, terrifying, paralyzing and cathartic as love comes from a hopeless place and ultimately goes right back, forever changing all involved, including us.