The 10 Worst Missteps of Madonna’s Career

Now hear this: I love Madonna. Always will. And that’s why I’m completely sensitive to her infuriating moments.

Recently, audio circulated of Madonna preparing for her new tour. In a short clip, she sings Lady Gaga’s “Born This Way” as a mashup with her own, similar-sounding “Express Yourself,” as well as the pointed track “She’s Not Me.” Yes, it’s a cute and witty barb, one that’s meant as a gentle affront to Madonna’s heiress apparent Gaga, but I’m not laughing. I’m not exactly weeping either, but I’m more annoyed than titillated. It’s just… not that funny? Or rather, too on the nose, petty, and not funny. For me, it’s of a piece with Madonna’s post-2005 career, a stretch where too much of her output and decision-making feels like the work of a canny assistant, someone who knows and can mime the ferocity of Madonna, but simply isn’t the queen herself. And what could be a more depressing sight than watching a hired hand manipulate the strings of our self-invented sorceress?

Thing is, it’s hard to believe Madonna cares about Gaga’s tricks, because she barely cares about her own recording career anymore. The anonymous barrage of MDNA – much like the Timbaland-overhauled Hard Candy — proves Madonna has no problem handing over creative control to someone who simply feels commercially legitimate, any hotshot whose involvement validates the old credo that Madonna knows what’s hot, maybe before we do. She’s lost all faith in her iconic powers, the chutzpah that defines the symbol of Madonna, and she feels she must use bankable names and means to remain a household name and re-confirm the boring tropes about her success (e.g. “She’s business-smart!”; “She’s constantly reinventing herself!”) that non-fans have begrudgingly given her credit for.

I want the Maodnna who feels like an effortless dictator, not the one who is mechanically compensating for lack of inspiration. I understand it’s not exactly easy to percolate with ideas in your 30th year as a pop star, but coasting on overworked blandness – and stupid digs at a great like Gaga — is no solution I can reasonably sit through.

That brings us to today’s topic: Madonna’s biggest career missteps. Because she’s the most meaningful pop icon to emerge in the past half-century, these moments don’t quite define her legacy, but they’re still noticeable blotches on the tapestry of Madonna’s career. Here are my choices for her 10 biggest duds.

10. I’m Going to Tell You a Secret


When MTV announced it was airing Madonna’s pseudo-sequel to Truth or Dare in 2005, fans gawked. Would we be in for another saucy, somewhat calculated, ultimately endearing documentary in the tradition of her 1991 black-and-white triumph? We sure weren’t: I’m Going to Tell You A Secret may have given us a glitzy glance at Madge’s Reinvention tour, but it ultimately put more distance between fans and the queen. Consider the cloying segments featuring a pontificating Lourdes, the eye-rolling moment where Madonna asks auditioning dancers if they “smoke grass,” and worst of all, the climactic trip to Israel at film’s end. It’s all a perfect encapsulation of the aloof self-importance I always want Madonna to lose.

9. The music video for “Celebration”

And speaking of Lourdes! The titular video for Madonna’s 2010 hits collection featured references to every lame thing that landed her in the tabloids that year. Look, there’s young, beautiful Lourdes donning a wedding dress and winking like her mother! (Ugh.) There’s Jesus Luz manning the turntables! (UGH.) There’s more of the unnecessary yoga gymnastics that Madonna insists we applaud! (I’m seething now.) “Celebration” felt like a desperate plea to non-believers, not a proud culmination of her generation in the business.

 

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