Taylor Swift’s 10 best music videos

ByQuyen Anne

Jan 11, 2024

Taylor Swift is the music industry’s ultimate chameleon. After launching her career as country’s next big thing back in 2006, the Grammy winner’s evolution as a pop princess will soon come to a head with the release of her fifth studio album, “1989,” out Oct. 27. Although the release is still a few days away, Swift has been busy promoting the album by dropping new singles and releasing outrageous music videos.

Though the twerk-heavy “Shake It Off” and the soulful “Teardrops on My Guitar” are in two totally different ballparks, both music videos express who Swift is at certain moments in time — and they aren’t the only ones.

In honor of the album’s highly anticipated release, take a look back at Swift’s 10 best music videos.

‘Tim McGraw’ (2006)

Before “Teardrops on My Guitar” became a mainstream success, there was “Tim McGraw.” The enchanting music video features the then-country crooner cozying up to a handsome suitor in — where else? — “a Chevy truck that had a tendency of getting’ stuck.” Swift disclosed to USA Today that the track was inspired by an ex-boyfriend.

‘Teardrops on My Guitar’ (2007)

You can’t expect to have a Taylor Swift list without the video that started it all. Released in 2007, “Teardrops on My Guitar” is an ode to Swift’s high school crush, Drew (played by “One Tree Hill” alum Tyler Hilton).

Swift stars as the pro-typical “girl next door” who fawns over her best friend. Unfortunately for Swift, Drew’s heart belongs to somebody else. Le sigh.

‘Our Song’ (2007)

Straying away from acoustic ballads, “Our Song” boasts a bit of country twang. Featuring a bubbly Swift hanging out on a front porch in a tulle dress, the blond beauty sings about her fairy-tale-like romance with an unnamed boy toy.

From cruising around in cars to late-night rendezvous, it seems that Swift was seriously smitten with a certain mystery man.

‘Love Story’ (2008)

The real title of this video should be “When Shakespeare Met Swift.” This period piece-esque video depicts Swift as a damsel in distress longing for her handsome prince (played by Miley Cyrus’ then-boyfriend Justin Gaston).

Although Taylor herself has yet to encounter a happily ever after in the romance department, the ending to this “Love Story” matches those of classic fairy tales.

‘You Belong With Me’ (2009)

Swift may look like a prom queen, but in the charming video for “You Belong with Me,” the songstress trades in her ball gown for a marching band uniform. Playing the geek next door, Swift pines for her quarterback crush (Lucas Till, better known as Havok in “X-Men: First Class” and “X-Men: Days of Future Past”) who is taken by the quintessential popular girl (played by a brunette T-Swift).

And while it may seem like the nerd will strike out in the end, sometimes it’s the nice girls who finish first.

‘Fifteen’ (2009)

Swift has quite the collection of famous friends, but hard-core fans of the singer know that Abigail Anderson is her longtime bestie and the inspiration behind “Fifteen.” Centering on the pair’s freshman year of high school, the soulful ballad details the triumphs of falling in love and what it’s like to fall too fast.

‘Mine’ (2010)

Perhaps Swift’s most memorable love song to date, “Mine” is a video scrapbook that captures the various (albeit precious) stages of a relationship. Swift plays a small-town girl who falls for a small-town guy (“The Covenant’s” Toby Hemingway).

Though their romance is seemingly picturesque (a proposal on the water, anyone?), Swift’s character fears that the courtship will crumble much like the marriage of her fictional parents. As you could probably guess, Swift and her man are chapel-bound in the end.

‘The Story of Us’ (2011)

Most of T-Swift’s tunes are drawn from her own experiences, and “The Story of Us” is no different. After encountering an ex-boyfriend at an award show, Swift was inspired to pen a track about when former flames see one another for the first time following the said split.

The video takes place in a prep school library and shows a newly single Swift still reeling from her breakup, and how she feels about seeing her one-time beau again.

‘I Knew You Were Trouble’ (2012)

Hell hath no fury like Swift scorned. The chart-topper ditched her country roots for a pop anthem about dating a man who did her wrong. The video stars former “Spider-Man: Turn Off the Dark” actor Reeve Carney as the bad boy who stole T-Swift’s heart.

Rumor has it that her whirlwind romance (followed by a highly publicized breakup) with One Directioner Harry Styles inspired the track.

‘Shake It Off’ (2014)

Swift’s most recent video is by far her peppiest to date. Released in August, “Shake It Off” is Swiftie’s attempt to tackle the haters and naysayers by living life as she chooses.

“We don’t live just in a celebrity takedown culture, we live in a takedown culture,” the singer dished on “Good Morning America” earlier this summer. “You have to not only live your life in spite of people who don’t understand you — you have to have more fun than they do.”

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