Merry Swiftmas: Taylor Swift’s best music videos from each era

NEW YORK, NEW YORK - NOVEMBER 12: Taylor Swift attends the "All Too Well" New York Premiere on November 12, 2021 in New York City. (Photo by Dimitrios Kambouris/Getty Images)
NEW YORK, NEW YORK - NOVEMBER 12: Taylor Swift attends the "All Too Well" New York Premiere on November 12, 2021 in New York City. (Photo by Dimitrios Kambouris/Getty Images) /

Taylor Swift has long been known for her amazing, high-production-value music videos. For this Swiftmas update, we’re looking at the best music video from each of Taylor’s musical eras.

Since the early days of her career, Taylor Swift has been making impressively constructed, high-quality music videos. One thing that sets hers apart from other artists is how many of them are narratively driven, with a full story being told within a few minutes. As part of celebrating Swiftmas, I’m sharing my favorite music video from each album’s era.

Debut: Teardrops On My Guitar

There are many fantastic videos from Taylor Swift’s first album, but “Teardrops On My Guitar” not only has an incredibly mid-2000s makeup look for Taylor but also captures the sort of storytelling that she would become known for. The video shows Taylor in a school, pining after her crush Drew, and in the hallway, library, and science lab. It captures the high school experience the same way that her debut album does.

Fearless: You Belong With Me

This is not just the best music video from the Fearless era, but Taylor’s best music video of all time, if you ask me. Starring Lucas Till and Taylor Swift (twice), it perfectly recreates the love triangle story of the song. Those notes through the window sequences have become iconic, as has Taylor’s Junior Jewels band camp t-shirt. It would be worth choosing just for the fun dress-up and dancing in her bedroom scene, but the dramatic ending at the school dance is top-tier teenage drama. And casting herself as the cheerleader villain as well as the wallflower protagonist? Pure genius.

Speak Now: The Story of Us

If you love dark academia vibes, then “The Story of Us” is certainly the music video for you. Many of Taylor’s videos in the Speak Now era were a bit more subdued than her Fearless ones, but having a video set in a library for a song based around stories and chapters is a clever touch. If the prep school tie and button-down look are a little over-the-top, maybe we can blame the popularity of Gossip Girl for that. Regardless, it’s a fun setting for a video, and Taylor and an ex awkwardly glancing at each other from separate study tables is certainly relatable for many who dated and broke up with someone they went to school with.

Red: I Knew You Were Trouble

The Red music videos saw a more mature version of Taylor Swift and this video certainly encapsulates that, as she sees her lover through everything from tattoo appointments to bar fights. It’s a grungier look for the singer than we’d ever seen before, complete with pink-tipped hair, as a whole relationship plays out onscreen with some poignant narration at the beginning and end of the video. It also stars Reeve Carney, from the cast of Hadestown on Broadway, who recently appeared as Tom Ford in the film, House of Gucci. The darkness of the video highlights that though the song is upbeat and fun, it’s about a toxic and painful relationship.

Red (Taylor’s Version): All Too Well Short Film

I couldn’t talk about the best Taylor Swift music videos without mentioning the new “All Too Well” short film that debuted along with Red (Taylor’s Version). The song, while a fan favorite, wasn’t a single on Red‘s original release and never got a music video, but now fans have an extended fifteen-minute-long film starring Sadie Sink and Dylan O’Brien. It shows the toxic and manipulative relationship depicted in the song, with several breaks for dialogue. It highlights the inequalities created by the large age gap described in the new lyrics of the extended version of the song and how manipulative the man in the relationship is.

1989: Blank Space

1989 saw Taylor Swift change her image, fully making the transition from country darling to pop superstar, but it also saw her playing with her reputation in the media on the track, “Blank Space.” The music video is a gorgeous depiction of the sort of glamorous, but crazy man-eater that the tabloids (and lots of online comment forums) liked to portray the singer as. Mainly filmed at Oheka Castle, the video was compared to Gone Girl when it was released for its themes. It not only is perhaps the most beautiful of Taylor’s music videos but also features her best acting performance.

Reputation: Look What You Made Me Do

The album Reputation saw Taylor Swift once again responding to the press’s portrayal of her. In this spooky video with frankly insanely high production value, we see a zombie version of Taylor, Taylor on a throne surrounded by snakes, and past versions of Taylor fighting each other. The video contains an incredible amount of Easter eggs for things that had been occurring in Taylor’s life, from the drama with Kim Kardashian and Kanye West to her relationship with Tom Hiddleston. Like “Blank Space,” the video satirizes the version of Taylor Swift that the media paints her as.

Lover: The Man

While most of the album Lover is a beautiful tribute to Taylor’s relationship with long-time boyfriend Joe Alwyn, “The Man” addresses the sexism that is rampant in the entertainment industry. In the music video, Taylor Swift is transformed into a corporate man with makeup and prosthetics. It’s very reminiscent of The Wolf of Wall Street, which is all too fitting considering the Leonardo DiCaprio reference in the song. We see the male version of Taylor man-spreading on public transit, with lots of young beautiful girls on a yacht, and getting praised for doing the bare minimum of taking care of a child. It’s a direct commentary on sexism in the industry and the video itself was both written and directed by Swift herself.

Folklore: willow

The past few eras have been much shorter since Taylor Swift started surprise-dropping albums. While Evermore never had any music videos, Folklore had a couple, and “willow” is absolutely beautiful. It continues what Taylor began in the “cardigan” music video, but also plays on the “invisible string” motif from the album. The costumes and sets are gorgeous and it once again proves Taylor’s abilities as a director.

Next. Celebrating 15 years since Taylor Swift the album. dark

What’s your favorite Taylor Swift music video? Is there a song that Taylor will be rerecording that you hope we get a music video for? Let us know in the comments or on Twitter.