Around this time eight years ago, Madonna collected her only major motion picture award to date: the Golden Globe for Best Actress in a Comedy/Musical for Evita.
That put her in the same class as heavyweights like Nicole Kidman, Julia Roberts, Sissy Spacek, and Judy Garland.

But our friend Oscar didn’t even notice.
And, unfortunately, that career-defining role was followed with a small string of big bombs (The Next Best Thing, Swept Away) and a ho-hum cameo in a James Bond flick, more notable for her controversial theme song than anything else. To wit, the biggest movie news for Madonna in the new millennium thus far has been that she was named the Worst Actress of the Century (!!) by the mean-spirited Razzie Awards.
Thanks to a record-setting number of citations over the years, she’s no stranger to those dubious “achievements.”

Is Madge really THAT bad of an actress? What’s with the disconnect between her revolutionary videos and live performances compared with her stabs at cinematic legitimacy?

With her ambition to act hardly a secret and a bushel of new films already in the works, here are a few guidelines that might help Madonna better choose her thespian battles.

It would be crass to say these roles required no stretch for Madonna. On the other hand, it would be disingenuous to say that elements of Madonna’s personal life didn’t creep into these major roles. A brash, streetwise bohemian? A coarse yet talented woman of ill repute? A tough-minded diva impervious to obstacles on her ascent?

Opposite Clive Owen in Guy Ritchie’s BMW The Hire: Star spot, Madonna riffed on her own notoriety so well as to generate true laughs. “Breathless” Mahoney from Dick Tracy was a perfect role at the perfect time for the post-1980s entertainer, effortlessly blending her famous sexuality and deft musical abilities.
And it doesn’t require explanation to claim her alleged non-performing for the documentary Truth or Dare (a.k.a. In Bed With Madonna) was out-and-out enthralling. Naturally, everyone suspects there was a lot of vamping for the camera’s sake; acted or not, it was an arresting performance.

Resounding duds like Shanghai Surprise, Body of Evidence, and The Next Best Thing (and Who’s That Girl and Dangerous Game and Shadows and Fog, etc.) required Madonna to abandon who she was and embody a character and flesh her out.

Some have suggested that Madonna, the woman, is too “larger-than-life” to inhabit someone else and dissolve into a role to the point of convincing audiences.
Valid or not, that argument is being very generous. Critics (and much of the public) mercilessly pummeled her headlining movies - and, to be fair and balanced, her 2003 appearance on Will & Grace (which I personally adored) - as at best stilted and wooden, at worse false.

Perhaps more of a critique and judgment of Madonna herself, the universal disdain for her fictional projections (or lack thereof) can’t be discounted. It’s always been trendy to put down Madonna’s acting abilities, so distilling an honest assessment is next to impossible.

Number Two: The smaller, the better.

Die Another Day, Four Rooms, Blue in the Face, and Girl 6 - and even her theater roles (Speed the Plow, Up For Grabs) -- weren’t debacles for Madonna because she graciously ceded the spotlight to other performers.

When the part is a small one, Madonna can be sublime. She seems to inhabit smaller characters skillfully, knowing the burden of the piece doesn’t rest on her shoulders. This bodes well for Guy Ritchie’s upcoming Revolver.

Number Three: Remember where you came from.

A glaring example of how strenuously Madonna “acts” is the array of accents she employs. Even sitting down for an interview becomes a performance.

Since more people tune in for a sit-down with Matt Lauer than would fork over ten bucks for a Madonna movie, most people get their fill of the inflections and London-by-way-of-Detroit-by-way-of-New-York lilts by catching snippets of her with journalists.

Understandably, this incredulity then spills into people’s gut feeling about her legitimate attempts at acting. Why would anyone bother to take someone who basically mocks herself seriously?

The greatest linguist in the world would be hard-pressed to place her Amber’s accent in Swept Away. Even more painful was that faux British twang of The Next Best Thing.
The biggest puzzle of that movie was not, as advertised, whether Rupert Everett as a gay man fathered her baby, but where on Earth her California yoga instructor character picked up such an unusual and distracting drawl. Everett and director Arthur Schlesinger should have thwarted that faux pas the moment she opened her mouth on the set.

With her newfound spirituality and a purportedly growing comfort in her skin, Madonna should shed the brittle voices she wears in public like so much armor.

Number Four: Stick to what you’re good at.

And for Madonna, it’s music. Some of her videos are mini cinematic masterpieces; Bedtime Stories, Express Yourself, Frozen, and Take a Bow jump to mind. Good direction and effective editing can capture Madonna’s emoting, and thus her message, in quick, four-minute visual bursts. It’s no coincidence that she barely utters a spoken word in any of them.

Her concerts, too, are tours-de-force and rival the greatest theater spectacles of all-time, melding Broadway, arena rock, and even circus production values. Throw a wig and a cool costume on the old gal, and she’ll have you bopping along.

She engenders a suspension of disbelief and allows the viewer to see, say, a geisha (Drowned World), a yenta at a beauty parlor (The Girlie Show), or an angst-filled repentant (Blond Ambition). She even reportedly drove some Re-Invention Tour goers to tears as a woman strapped into an electric chair.
When the music stops, however, our problem begins. Most critics agreed the only tolerable part of Swept Away was the musical interlude, with Madge in full glamour mode. Evita was, when you boil it down to its parts, a giant music video.

That’s precisely why Madonna was born for the part, letting her well-honed miming follow the impressive tracks she had already laid down. The club crooner in Vision Quest, if that really counts as a “role,” was a nice way to plug Madonna the singer without inducing vomiting among moviegoers. And, again, Dick Tracy was an appropriate platform for Madonna to ostensibly snag Warren Beatty as the quasi villain while really a showcase for tackling Stephen Sondheim tunes.

Who knows how different things would be if Madonna had been cast, as long-planned, in the Chicago movie. Imagine “Grammy-, Golden Globe-, and Oscar-winning megastar Madonna!” Hey, two out of three ain’t bad.

Speaking of the Oscars, recognizing Hollywood’s disdain, it took cajones to perform Sooner or Later (from Dick Tracy) at the 1991 Academy Awards with such spunk and sultriness … and even larger cajones to bring Michael Jackson to the event as a “date.” Facing an outright snub for an acting nomination in 1997, it was nothing short of grace that found her on the Academy Awards stage again that year, shakily but surely crooning You Must Love Me, the lyrics of which operated on so many levels that night.

If that’s the closest Madonna ever gets to Oscar, well, then that’s still something to sing about.