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What do Barbie, the late Alexander McQueen, the Disney villain Malificent, Lady Gaga, Wonder Woman, Cyndi Lauper, the clothing line Rodarte and the animated character Hello Kitty have in common with fine artist and filmmaker Cindy Sherman?

Each has inspired M.A.C. cosmetics in the creation of makeup palettes that reflect their highly individuated aesthetics.

If Rodarte, or la donna mobile Lady Gaga were edgy choices, Sherman – whose line appears this fall – is the most daring yet.

Images of the three "faces" Sherman has created and the associated products have already appeared. In these self-portraits, Sherman is made up, variously, as a clown, what appears to be a mentally-ill prom queen and a drunken sophisticate: The images are variations on the artist's large body of subversive autobiographical work.

Last fall, Sherman collaborated with Balenciaga for the annual after-hours shopping event called Fashion's Night Out. Creative director Nicolas Ghesquière commissioned Cindy Sherman: Untitled (Balenciaga), a series of self-portraits featuring borderline grotesques dressed exclusively in the line's couture.

The effect was troubling, disruptive. Did the frightening, ugly subjects suggest something inherently hideous about Balenciaga, about haute couture's rarefied circle? Or did these portraits simply communicate the fact that the fashion house could afford Sherman (whose work sells for millions of dollars) to model for them?

Both are true.

The M.A.C. line is a still more subversive a move, considering the relative accessibility of the brand and keeping in mind that high fashion's relationship with the grotesque, in iconography, is far better established.

Yes, makeup is central to the depiction of monstrosity in cinema and art, but the huge cosmetics industry is rarely, if ever, self-reflexive.

Leaving aside its deep roots in race and class (fabricated pale skin, historically, has long been the desired look of the female aristocrat), makeup is most closely associated with female beauty and is always sold as such.

Yet Sherman's work is the rough equivalent of a mascara wand in the eye: What does this mistress of disguise's unsettling work have to tell us about our love affair with the colours, textures and fragrance of makeup?

Sherman, like U.S. photographer Nan Goldin, became prominent in the 1970s, when fashion – in the underground where it inevitably begins – was being forged by an epicene, polysexual subculture.

John Waters's early and most trangressive films begin around this time as well and emerge from his first (never shown commercially) 16 mm film, Eat Your Makeup (1968).

In the film, Divine plays Jackie Kennedy; another of his Dreamland babes (Maelcum Soul) kidnaps girls and forces them to model to death. The women caress and taste, then eat their makeup: This notion progresses, however diabolically, from both the sensual quality of cosmetics and something else.

In the 1970s, politicized women were troubled about their relationship to makeup, the daily wearing of which feminist goddess-leader Germaine Greer deemed "a psychic problem."

If makeup, like a mask, both conceals and reveals our identity, the desire to ingest makeup has a lot to do with our desire for wholeness, which was the central female quest during and after the equal-rights movement.

Sherman has long politicized the idea of the female subject through her portraiture (in which she is both object and subject) and in the changing nature of her self-representation.

In her maturity, she has shifted from doe-eyed, plasticized ingenue or fetching corpse to a modernized Bride of Frankenstein: In the 1990s, she, very fashionably, interpolated doll parts and mutilation into her work. And now, she seems preoccupied with the less shocking, more complex modifications that find an analogue in aging.

The Balenciaga women are vulgarians or near-beauties – in ruins.

The M.A.C. women are extreme types with one commonality: Each is engaged, theatrically, with her hideousness.

The pink-wigged clown, painted to seem both happy and sad, responds to a fairly constant critique about makeup being axiomatically clownish, while advancing a sense of both playfulness and misery.

The electric-pink-cheeked prom queen is both vacuous in her prettiness (her hair falls to her shoulders in artful ringlets) and terrifying: Her mouth is slashed like the Joker's, and the portrait is, indeed, a serious joke about the polemical nature of makeup. That is, it asks us to look deeply inside any portrait of a plainly pretty girl and wonder what might lurk or flourish there.

Finally, the middle-aged woman, who looks hard and coarse outfitted in chic leopard and gold and sporting vivid purple lipstick, is a study in the vulgarity of garish concealment and the triumph of embellishment.

So many contradictions, all funnelling into one cogent argument about the versatility and dynamism of makeup.

Critic Laura Mulvey refers to "the culture of appearances" in Sherman's work, to the tension, in some shots, between the carefully applied makeup and the imperfection suggested by the subject's lack of ease.

Once, it was a political act to opt out of wearing makeup. Now, with Sherman in the mix, it would appear that opting in, with a few carefully phrased (rendered, that is) objections, is political as well.

Who are women, really? This September, with an array of tubes, sticks and pots, we will have even more ways to make up the answer.

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