Taylor Swift's Getting Funnier

It seems one of the corporate fat cats (probably a literal cat) who works at Republic Records held a Dasani bottle of acid up to Taylor Swift’s collection of deadstock Dôen dresses and threatened to ruin them all with it unless she made a promotional TikTok teasing her upcoming album, Midnights. The result is the following TikTok, the first of a series called “Midnights Mayhem with Me.” Accompanied by ironic easy listening music and festooned in 70s gold tones, Swift whirls an old timey Bingo ball machine and reveals the name of track 13 on the album: “Mastermind.”

It’s pretty funny! For Taylor. She’s getting better.

This has become the subject of heated debate amongst my coworkers and me: some of the colleagues whom I respect the most happen to be diehard Swift fans, and they tell me she’s “always been funny.” I’m not convinced. I am a late-in-life Swiftie who didn’t appreciate her musically until I was 28 years old, but I’ve been aware of Taylor Swift’s attempts at comedy since long before I was converted as a fan.

She’s approximated a particular style of “humor” based mostly on her interest in baking, and she has coasted on it far too long. This sort of thing does not work unless you are Zooey Deschanel in a sitcom and you have the comedic stylings of Jake Johnson to foil your performance. At best, it’s disingenuous. At worst, leaning into your demure purity as a half-joke can have the opposite intended effect, especially when you’re attempting to do it in opposition to what you perceive as the ass-shaking debauchery of hip-hop and pop music.

An early example of this is the “Thug Story” video, a parody of “Love Story” she made in 2009 with T-Pain.

I think the joke here is: she’s rapping about cookies, not crunk juice bombs and Oakley shades like T-Pain does.

She pulls a similar move in the music video for “Shake It Off” in which she “comedically” tries and fails to be good at dancing and wearing gold hoops.

She’s moved on from this sort of thing, presumably with the help of a writers’ room of Harvard Lampoon alumni, and it’s working for her. Besides being Patient Zero for the “millennial pause,” her TikTok is light and fun, and she hasn’t used the term “this sick beat” even once. When it comes to her comedy chops, she’s on a good path.

Up until now, there are only two times I’ve genuinely laughed at something Taylor’s said, and neither was on purpose. One: when I misunderstood the the lyric, “Does she mouth, ‘fuck you’ forever?” in the song “mad woman” as “Does she mouthfuck you forever?” Two: When she sang “I cried like a baby coming home from the bar” in the bonafide banger “Cruel Summer.” Ha! Why is a baby at the bar?! Now that’s comedy.

But her TikTok’s winning me over in a way that feels more fitting with an actual sense of humor, like in this video where she tries to dress in the enormous leather pants/small bra look her friends over at HAIM have made famous. She’s still posturing herself as a little bit adorkable, but at least she’s getting over herself and showing a little midriff while making herself the butt of the joke.

The bar’s low, but I believe that she’s got this, so long as she listens to her better demons and there’s not another Reputation era incoming. That was even less funny than the music video for “ME!”