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.

8. The children’s books

Sure, we’ve learned a lot from Madonna. She taught us that ambition should be endless, sexuality should be staunchly self-owned, and superstardom can be its own artistic canvas. But we don’t need our kids to read scrolls of Madonna’s “lessons” before kindergarten graduation, do we? When the Kabbalah-entrenched Madge released her first children’s book, The English Roses, I pretty much jackknifed in pain. The moral of the story? The mean blonde girl at school is really just jealous of the thoughtful brunette. Uh, cool? Madonna should’ve pitched this as a variety show called “The Lourdes Ciccone Reassurance Hour.”

7. Shanghai Surprise/Who’s That Girl

With the exception of her short stint on Broadway in David Mamet’s Speed the Plow, Madonna’s only true mistake in the ‘80s was her starring presence in 1986’s Shanghai Surprise and 1987’s Who’s That Girl.Who’s That Girl was simply a boring film where Madonna honked and screeched like Judy Holliday on psychotropics, but Shanghai Surprise was a particularly rough patch. It gave us the nervous, clueless Madonna who seemed to be acting for her husband Sean Penn’s approval. This was a far cry from the bemused, street-rat appeal of her Desperately Seeking Susan days. It felt like the worst possible representation of “Open Your Heart’s” signature bleat: “I’ll make you love me.”

6. The Ray of Light fallout

I like Ray of Light. I even like that it scored Madonna a few Grammys. But I don’t like what that album did to Madonna, who routinely calls it her favorite personal effort. Following the album’s success in ’98, Madonna placed more stock in sharing the hackneyed revelations of her self-professed spiritual journey than ever. Though her followup, 2000’s Music, was a phenomenal dance album, it featured a swarm of Kabbalah-tinged platitudes. “Paradise (Not For Me)” is ruined by that vague “light” references. I can note the same kind of problems in every album thereafter, and I think we can trace her annoying didactic streak back to the adult-contemporary electronica of Ray of Light.

5. American Life

I’d argue that Hard Candy is a worse album, but 2003’s American Life gave us one cringe-worthy spectacle after another. And while Hard Candy was disposable, American Life was a reeking turning point. The meaningless, flag-dappled video for “American Life”? The rap about lattes and “shot-tays”? The tuneless condemnation of materialism in “Hollywood”? The flagrant “artistry” of it all? It was actually a valiant attempt at a breakthrough, but it came across as a garbled, songless drone rendered in ugly electroclash.

4. W.E.

There are merits to Madonna’s 2011 directorial bid for Oscar glory: The fabulous costumes! The De Beers commercial lighting design! Andrea Riseborough’s vivacious portrayal of Wallis Simpson! James D’Arcy’sPerkins-ian good looks! But the fiasco surrounding the film’s awful reception at the 2011 Venice Film Festival – as well as the dubious intentions behind Madonna’s investigation of the pretty-much-execrable Edward VIII and Simspon’s lives – torpedoed this venture. The overlong film left me with one unsettling question, one I hope to never again ask of Madonna: What are we trying to prove here?

3. Swept Away

You have to admire Madonna’s desire to honor the legacy of Lena Wertmuller, the first woman to be nominated for the Best Director Oscar, with a remake of her ‘70s jam Swept Away. That’s where the joy ends. Madonna was catastrophically unlikable in this flop, and I shudder thinking of her batty lip-sync ofRosemary Clooney’s “Come on a My House” during one key scene. Worse, it tainted the perception of her marriage to then-husband Guy Ritchie, and I remember rooting for that to work out.

2. Evita

Controversy! I don’t care that Madonna won the Golden Globe for Best Actress in a Musical/Comedy (beating Frances McDormand in Fargo, bizarrely enough), racked up a couple of Billboard hits as Eva Peron, or acted alongside the scintillating Antonio Banderas. Evita represents everything that Madonna shouldn’t be about: self-conscious vocal prowess, prim regality, stilted dialogue, and worst of all, someone else’s vision. I treat this film as a void in Madonna’s career, a time when she began to value pretension over performance, critical respect over personal urgency.

1. The Britney/Christina liplock at the 2003 VMAs

I can forgive the other nine items on this list. Easily. They’re glitches in Madonna’s carnal machine, mere kinks in an otherwise pulsing fame monster. But I’ll never forget the horror of watching Madonna lock lips (or “share energy,” as she put it) with the two shallowest excuses for Material Girl descendants on this Earth. AsBritney and Christina chirped “Like a Virgin” in wedding dresses while Madonna descended a cake in an equestrian groom’s regalia, the message of the awful circus was clear: Madonna was “passing the baton” and submitting to the freakish popular opinion that, yes, manufactured Britney Spears and artistry-deaf Christina Aguilera are Madonna’s true heirs. After all, they sometimes have blonde hair too! They even dance! Sometimes they’re “sexual,” when the choreography calls for it! Call me a far-out Madonna disciple, but Britney and Christina exhibit none of Madonna’s self-invention, wit, or throbbing humanity. None of the charisma, none of the half-winking, half-committed self-lionization. For Madonna to legitimize some jackassRolling Stone critic’s idea that she’s simply Old Britney remains my own personal version of soul torture. As far as I’m concerned, Madonna can never get lower than this. Justin Timberlake, I’m still exchanging mystified glances with you.