Warm-Up: Music Videos and the Director’s Chair

Unofficial fan trivia. Boston Made is not affiliated with, sponsored by or endorsed by Taylor Swift or her team. Every fact below comes from her public career.

Taylor Swift’s music videos have always been events, but over the last several years she has also become one of the most decorated directors in the format. This warm-up follows that path, from big-budget collaborations to her own director’s chair and the honor she received at the 2026 VMAs.

The early blockbusters

Before she directed, she worked with some of the best-known names in music video. Joseph Kahn directed “Blank Space” and “Bad Blood,” and “Bad Blood,” featuring Kendrick Lamar, won the Grammy for Best Music Video and her first MTV Video Music Award for Video of the Year in 2015. “You Need to Calm Down” won Video of the Year at the VMAs in 2019.

Those videos were big, star-filled productions, and they set the expectation that a new Taylor Swift video would be talked about for weeks. They also gave her years of time on professional sets, watching how directors, cinematographers and editors built a story in a few minutes of film.

Her directing debut: “The Man” (2020)

Her official solo directing debut was the video for “The Man,” from Lover, released on February 27, 2020. It won Best Direction at the 2020 MTV VMAs, making her the first solo female director in the show’s history to win that category.

That was a first for the category and an early signal of how seriously she took the job. It would not be the last time she won it.

She kept going. She directed the videos for “cardigan” and “willow,” the lead singles from folklore and evermore, and then the Midnights videos, including “Anti-Hero,” “Bejeweled,” “Lavender Haze” and “Karma.” She also directed “I Can See You (Taylor’s Version) (From the Vault)” and “Fortnight,” featuring Post Malone, from The Tortured Poets Department.

All Too Well: The Short Film

Her most ambitious directing project came out on November 12, 2021, the same day as Red (Taylor’s Version). All Too Well: The Short Film, which she wrote and directed, set the 10-minute version of “All Too Well” to a story starring Sadie Sink and Dylan O’Brien.

It won the Grammy for Best Music Video, and it won Video of the Year at the 2022 VMAs. That began a streak: “Anti-Hero” won Video of the Year in 2023 and “Fortnight” won in 2024. By then she held the record for most Video of the Year wins, with five, including three in a row. She has also won Best Direction at the VMAs four times.

The Showgirl videos

She stayed behind the camera for her 2025 album. She directed the video for “The Fate of Ophelia,” the lead single from The Life of a Showgirl, which is built around showgirls and fame. “Opalite” followed with a video she wrote and directed with cinematography by Rodrigo Prieto. It premiered on Apple Music and Spotify Premium on February 6, 2026, and reached YouTube two days later. “Opalite” also became her 14th No. 1 single that month. A third video, for “Elizabeth Taylor,” used footage from the actress’s films and archival newsreels.

A record night at the 2026 VMAs

The 2026 MTV Video Music Awards were held on September 27 at the Peacock Theater in Los Angeles. That night:

• “The Fate of Ophelia” won Video of the Year, extending her own record in that category. She dedicated the award to Dolly Parton.
• She received the first-ever Artist Director Honors, a new award for musical artists whose work behind the camera has advanced the art of the music video. Dakota Johnson presented it.
• She became the most-awarded artist in VMA history, breaking a tie with Beyoncé.
• She premiered “Patient Zero,” a new song from The Life of a Showgirl: The Encore, with a video she directed starring Colin Farrell and Dakota Johnson.

In accepting the honor, she said she has been part of making 60 music videos and has written and directed 18 of them.

Watch the categories when you study. Video of the Year honors the video as a whole, while Best Direction honors the director’s work specifically. She has won both, often for the same video, and trivia questions like to test the difference. “The Man” won Best Direction but not Video of the Year. All Too Well: The Short Film won Video of the Year and a Grammy. The new Artist Director Honors is not tied to a single video at all; it recognizes a body of work.

How to remember it

• Solo directing debut: “The Man” (2020).
• Grammy-winning short film: All Too Well: The Short Film (2021).
• Video of the Year streak: 2022, 2023 and 2024, then again in 2026.
• New in 2026: the first Artist Director Honors at the VMAs.

One last study tip: when a question names a video from 2020 onward, the safest assumption is that she directed it herself. Most of her major videos since “The Man” have carried her name as director, which is exactly why the VMAs created a new honor for her work behind the camera.

The Swiftie Finale opens Friday, Nov. 13 at 1:13 p.m. ET.