I know what you’re thinking: “Valentine’s Day” is way too high on this list. Two counter-arguments: this is my list, and “Valentine’s Day” is a fluffy, silly performance that ended up generating way better future content as it pertains to Taylor Swift. Hear me out.
After movies like “Love Actually” and “He’s Just Not That Into You” wove together a whole bunch of love stories connected by tenuous threads, Hollywood decided to go back to that well again and again. So, unsurprisingly, one of those giant ensemble movies ended up being set on Valentine’s Day. Swift plays high-schooler Felicia who’s obsessed with her boyfriend Willy (Taylor Lautner), and the scene everyone remembers is the one where Felicia is being interviewed by a local news organization about “young love.” She immediately says she’s “not the cheerleader” to Willy’s track star — quite obviously referencing the “cheer captain” from her hit “You Belong With Me” — and then shows off the moves she learned on the dance team. Honestly, she’s funny. She takes her terrible dance routine deadly seriously! It’s a good bit!
Here’s what’s important, though: without her performance in “Valentine’s Day,” Swift and Lautner never would have dated. Without their brief relationship, Swift never would have written perhaps the only song where she apologizes to a boy — the pained, exquisite “Back to December” from “Speak Now.” The two never would have rekindled their friendship and Lautner never would have filmed the music video for the “Speak Now” vault track “I Can See You” in 2023. Consequently, Lautner never would have backflipped down the Eras Tour stage that year. See? I told you. “Valentine’s Day” deserves this spot.
