What the Hell Is Going on in Madonna’s 50 Questions Video?

It’s impossible to make a list of musical provocateurs without Madonna immediately springing to mind. The pop star was burning crosses long before Demi Lovato was laying atop them on their album cover. She was famous for being Italian before Lady Gaga could ever utter the words “I’m Italian” in every interview. She paved the way for Addison Rae, which is a lovely rhyme but also a true fact—there would be no TikTok dance crazes if Madonna didn’t help make choreography an essential part of pop stardom.

But recent years have seen Madonna more reclusive. After the release of her last album, Madame X, in 2019, the icon faded back behind our screens during the pandemic, becoming as famous for her constant Instagram shapeshifting as she was for her decades of chart-topping hits.

One could consider this part of Madonna’s landscape of career transformations—after traversing nearly every musical genre over four decades, maybe the only way to keep us guessing was to be an alien one day and part of a movie theater janitorial staff the next. If you wanted to see Madonna unfiltered, both literally and figuratively, you’d have to catch a late-night, hour-long Instagram Live with Diablo Cody.

That’s why it was so surprising to see Madonna casually throw up an intimate, self-produced video on her YouTube channel this week, in which she answers a series of questions to promote her new remix album Finally Enough Love: 50 Number Ones. It would seem that all great Alien Superstars must come back down to Earth eventually, because this is Madonna at her most normal in years.

Of course, normal for Madonna is still pretty outlandish. But the real charm of this video is watching her try to pair her proclivity for banal, expectedly provocative statements with totally genuine answers to the questions she’s asked. Together it makes for seven minutes of whiplash-inducing hilarity.

The video lifts its conceit from Vogue’s famous 73 Questions format, in which celebrities are followed around by a cameraperson being asked PR-rep-approved questions and giving overly rehearsed answers. As Madonna’s done throughout her entire career, she’s decided to inject a little excitement and mystery into the structure.

For reasons that are never explained, the entire video is framed like a Pokemon game, with the tally of questions in one corner and Madonna’s initials in the other, all glowing with shiny chrome lettering. For the entire video, you’ll half expect to suddenly see one of the captions say, “A Wild Madonna Appeared!” Madge would then engage in a raucous duel to the death with the camera person. To borrow Pokemon lingo: “Madonna, a psychic Pokemon, used Cone Bra.” It’s super effective!

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In terms of actual substance and insight, there is little to be found here. Sure, there are definitely some revelations that fans will be excited by—Madonna wants to revisit House music! The hardest video she ever filmed was for “Die Another Day”! Madonna was one of five people who enjoyed Elvis!. But the fun really comes from watching her try to fiddle with this new and unusual video format.

There’s something decidedly ghoulish about watching Madonna running around her farm with no pants on, trying her best to pair sincerity with sexuality and miss the mark entirely. At one point, when asked what people would be surprised to learn about her, she responds, “That I hate being asked questions!” and takes off in a dead sprint into the black of the night.

If you told me this footage was found at the bottom of a well in Poughkeepsie with a bunch of animal skeletons dating back thousands of years, I wouldn’t bat an eyelash. That’s just the vibe.

Several times throughout the video’s duration, Madonna’s mic pack is compromised by a gust of wind, making her answers unintelligible. And even when you can actually understand her, things aren’t much clearer (and not just because Her Madgesty sucking on her grillz the entire time muddles her words to near incomprehension).

The number of times that Madonna mentions the act of coitus must set a new record. When asked what her mantra in life is, Madonna spins around 180 degrees at a breakneck speed and stares into the camera for three uninterrupted seconds, eyes burrowing into your soul: “Sex.” Moments later, she arrives at her property’s horse stables—the great focal point of any home—and grabs some carrots. “Remind you of anything?” she asks. Roaming around with Madonna is worse than sitting in a conversation at an 8th Grade lunch table.

And yet, I don’t know that I’ve laughed harder all year than when Madonna makes a ridiculously dumb joke about big dick being her favorite snack and immediately follows it up with the answer to her life’s greatest achievement, saying with 100 people earnestness, in a low and completely straightforward voice: “My six amazing children.”

Aside from the video’s intrinsic silliness, it does also offer a few gems, like when Madonna’s asked if she has difficulty finding inspiration in a world that’s so different from when she first started her career. “There is no end to the inspiration,” she says. “If you’re a curious person, and you pay attention to life, you will never stop being inspired.” That’s some actual, real advice right there! Shocking coming from the woman who just took a bite of a phallic carrot after feeding it to her horse.

It’s plainly obvious from the jump that these questions were scribbled down on some old doily by Madonna herself, as evidenced by her being asked what her favorite song from Madame X is. That’s something that not even the most hardcore of Madonna stans would be inclined to inquire about.

But hasn’t Madonna earned the right to be a little self-indulgent? It’s nice to see her casually interact with the public at large like this, free from whatever proto-technological, hyper-advanced filters she’s slapping on her visage before posting to Instagram. Even at her most chaotic, Madonna is always endearing.

Give her 50 more questions next month—hell, give her 100! Put her in increasingly exotic and inexplicable locales. I want to see Madonna, answering question number 82, while strapping herself into a wetsuit and getting ready to swim with sharks. “God, it’s riding up my ass—there’s something I’ve said once or twice before,” she’d say with a wink. “Oh Madge,” I’ll say with a warm laugh, “never change.”

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