At the 2023 GRAMMYs, Taylor Swift won Best Music Video for her short film set to the 10-minute version of "All Too Well."
It's a golden gramophone the singer has won once before, nearly a decade ago for the star-studded visual to 1989 single "Bad Blood." But this win was different. As Swift collected the 12th GRAMMY of her storied career, this victory came from a video she had single-handedly directed; it also marked the first time an artist won the category for a video they directed solo.
Delivering iconic visuals is nothing new for the superstar, either. After all, she's been doing it from her earliest days as a teenage wunderkind known for penning diaristic country-pop hits like "Tim McGraw," "Our Song," "Love Story," and "You Belong with Me." But over the years, Swift's precision in executing her singular, cinematic vision has only gotten more creative, more exact and more ambitious — and now, those talents are GRAMMY-winning.
To celebrate Swift's big GRAMMY win for "All Too Well: The Short Film," GRAMMY.com has distilled her extensive filmography down to the 11 most essential and unforgettable music videos in the Swiftian canon — from "Teardrops on My Guitar" to her latest No. 1 smash "Anti-Hero."
Check out GRAMMY.com's picks for the most iconic Taylor Swift music videos below.
"Teardrops on My Guitar" (Taylor Swift)
Although it was only her second single, the video for 2006's "Teardrops on My Guitar" contains many of the hallmarks for what would become Swift's signature visual aesthetic throughout her early career. Unrequited love interest in the form of One Tree Hill's Tyler Hilton? Check. An iridescent gown fit for a fairytale? Check. A narrative arc that establishes our girl as the underdog, who you can't help rooting for to get her happy ending? Check and check.
"You Belong With Me" (Fearless)
Is there any video more quintessential from Swift's country era than the one for "You Belong With Me"? Not only did the Fearless visual give Swifties their queen in her now-iconic "Junior Jewels" T-shirt, but it established the goofy side of Swift's personality — as yet unseen in her filmography — as well as her willingness to embody characters in her videos, like the brunette mean-girl of a cheerleader and an ultra-relatable band geek who are competing for the heart of the hunky boy next door.
"Mine" (Speak Now)
"Mine" was the lead single for Swift's third album — not to be confused with fellow Speak Now single "Ours," which led off the 2010 LP's deluxe repackaging. And though she'd dabbled in the past on videos for "I'm Only Me When I'm With You" and "The Best Day," the song marked the pop star's first true directorial effort helped along by co-director Roman White. And she was clearly taking notes that would inspire her future work during the process — just watch the scene where she and her rakish, blonde fiancé get into a screaming match in their kitchen and tell any Swiftie it doesn't look familiar…
"Everything Has Changed" feat. Ed Sheeran (Red)
This 2012 collaboration with Ed Sheeran upped the ante in Swift's videography by handing off the bulk of the storytelling to other people entirely — in this case, a pair of elementary schoolers portraying younger versions of Tay and the "Thinking Out Loud" crooner. The close friends and frequent collaborators only appear in the final moments of the video, but the kids and their adorable story would pick up nearly a decade later in the visual for the pair's 2022 duet remix of Sheeran's "The Joker and The Queen."
"Blank Space" (1989)
What does Swift do when the media paints her as a serial dater — verging on maneater — who's constantly burning her way through a revolving door of famous men? Write a smash hit about it, of course. With help from Joseph Kahn, Swift turns tabloid fodder into cinematic gold by casting herself as the unhinged nightmare dressed like a daydream, always ready to make the bad guys good for a weekend and add their names to her little black book. Too bad the poor fools won't find out until it's too late that their names are in red, underlined…
"Look What You Made Me Do" (reputation)
#TaylorSwiftIsOverParty? As if. With the release of the "Look What You Made Me Do" video, Swift officially entered her reputation era and shifted her skewed public perception off its tilted axis and back in her favor. Yes, there were snakes serving tea, bathtubs filled with diamonds, and a Taylor or two for every era that had come before. But the true feat of the glossy, karma-fueled visual was reminding the superstar's fans, doubters and haters alike that her ability to come back from the proverbial dead with a smash single in hand will always be stronger than anything thrown at her.
"The Man" (Lover)
For her solo directorial debut, Swift wanted to make both a statement and a splash. So she chose to skewer the sexism and toxic masculinity she's endured throughout her career as "The Man," cleverly dressing in drag as a rich, cocky manspreader by the name of — you guessed it — Tyler Swift. As has become custom over the years, the music video was filled with Easter eggs and cameos from famous faces like TikTok star Loren Gray, Dwayne Johnson and even her own father. The video eventually made history as well, when Swift became the first solo female to ever take home the prize for Best Director at the MTV Video Music Awards in 2020.
"cardigan" (folklore)
Filmed at the height of the pandemic, Swift proved with the video for "cardigan" that she is always capable of creating magic, even in the most challenging of circumstances. Taking cues from the fantasy and period films she had devoured during the early days of quarantine, the visual took a more fantastical turn than many of the past videos in the star's filmography. As the sole star of the show, a nightgown-clad Swift is transported to magical worlds by her trusty piano — a perfect parallel to the fictional worlds she dreamed up on folklore.
"willow" (evermore)
When evermore arrived by surprise just five months after its older sister, Swift announced that she was venturing deeper into the metaphorical woods. And with that, the music video for "willow" picks up right where "cardigan" left off. The clip doubles down on the fantasy of folklore by setting the singer on a journey filled with witchcraft, scenes straight out of a storybook, and an onscreen reunion with Taeok Lee, who last appeared as a backup dancer on the Red Tour in 2013.
"All Too Well: The Short Film" (Red (Taylor's Version))
There was really only one way to do the mystical 10-minute version of "All Too Well" justice after Swift dug it out from the vault for Red (Taylor's Version) — a short film, directed by Swift herself. Enlisting actors Dylan O'Brien and Sadie Sink as the doomed lovers at the center of the autumnal tale, Swift wrote the treatment, took charge on set, and manifested her creative vision with her most fully-realized project to date. The sweeping, 15-minute mini-movie soon inspired Swift to write and direct her first feature film, and helped the singer win the 2023 GRAMMY for Best Music Video.
"Anti-Hero" (Midnights)
"It's me, hi, I'm the problem, it's me." With that witty inner dialogue, Swift introduced Swifties to the most hilariously self-destructive version of herself. But even self-loathing looks like a blast through the superstar's point of view, whether she's outrunning ghosts dressed in whimsical '70s-style bedsheets or commiserating with her gigantic monster of a doppelgänger who just wants to be part of the gang.