Which Female Pop Star Makes the Hottest Guy?

As Drag Race winner Sasha Velour once rapped, “Gender is a construct. Tear it apart.” On Thursday, Taylor Swift took that as a mandate for her video for “The Man.” Using makeup, prosthetics, and some lace front facial hair, Swift turned herself into a man (resembling something of an unholy mix of Jared Leto and Scott Disick) to poke and prod at double standards and gender roles.

Of course, as there are literally no original ideas left in this world (something Taylor Swift knows all too well), Swift was not the first female singer to bend gender for both promotion and art.

While stars like Beyoncé, Shania Twain and Madonna have played with a sort of soft butch androgyny before, several others have gone all the way into drag king territory. Everyone from Mariah Carey to Charli XCX have stepped into men’s shoes, but the question remains: which of these gender benders makes the most appealing package?

Taylor Swift

“Total ass bro” is what Taylor Swift was going for with her “The Man” character, and she hit it out of the park. You just know this is the kind of guy who only pleases a woman when he leaves her alone, and only tips more than 15 percent when he’s throwing money at strip clubs. In fact, he’s the exact kind of guy you want Jennifer Lopez and Constance Wu to role up on and scam in Hustlers.

And, yet, some of you out there would probably be into him. Consider therapy.

Gwen Stefani

The video for No Doubt’s “Ex Girlfriend” involves Gwen Stefani hatching an elaborate plan to beat up her ex-boyfriend, who, come to think of it, is the kind of guy Swift is spoofing in “The Man.” This means donning a disguise to get access to the men’s restroom. Stefani’s look here is more of the “quick drag” variety: it’s just a fake mustache, sunglasses and a hoodie, and, yet, the effect is like Italian dandy who just really got into streetwear. Not bad.

Katy Perry

Perry dressed up as a ’70s game show host for an appearance on Ellen, but the main takeaway here is that Perry is one of those stars you never see without eyeliner, even when dressed as a man.

Miley Cyrus

Cyrus went undercover as a male production assistant on an episode of RuPaul’s Drag Race, and the illusion was done well enough to trick actual drag queens for at least a few minutes. Well, until Silky Ganesh got involved.

Charli XCX

Troye Sivan and Charli XCX portray numerous ’90s figures in their “1999” video, with Sivan handling most of the male parts and Charli the female ones. However, XCX held the part of Steve Jobs for herself. A hipster nerd in a turtle neck with pouty lips? He would be very popular in certain parts of Brooklyn.

Selena Gomez

Did we, as a society, fully comprehend how totally wild the plot of Selena Gomez’s “Bad Liar” music video was? She plays four characters caught in a bizarre love quadrangle, except three of those characters are a nuclear family. (The daughter catches the dad, who is a teacher at her school, flirting with the blonde gym teacher and the mother finds out, and at the end it’s revealed the daughter is in love with the gym teacher, too. Lady Gaga could never). Anyway, Selena as “Father/Science Teacher” looks like a Jason Schwartzman character in a Wes Anderson movie, which, we guess is someone’s type.

Lady Gaga

Speaking of things we still don’t fully comprehend: Lady Gaga’s Jo Calderone character. He showed up in her “Yoü and I” video, at the VMAs, and on a magazine cover—and was never heard from again. Yet, he does kind of look like the kind of guy who could have played in Strokes-era garage band and briefly dated Chloë Sevigny.

Mariah Carey

In her “Obssessed” video, Mariah Carey plays her own male stalker who, in a twist on the “Stan” video, is revealed to essentially be Eminem. The level of shade: some of Mariah’s finest. The visual affect: still sort of off-putting.

Barbra Streisand

Long before Taylor Swift was even born, Barbra Streisand directed herself in the musical Yentl, in which she plays a woman who dresses as a boy in order to get an education. (Streisand became the first woman ever to get a directing nomination from the Golden Globes in the process.) In the movie, Yentl does manage to catch the eye of a few admirers, but still, essentially, just looks like Barbra Streisand with short hair.

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