There was a time when everyone wanted to know the real Cindy Sherman. These were the '80s when art patrons could be measured in kilos and the only thing better than having an authentic Schnabel pinned to the wall of your studio loft was owning a photograph—two smiles and a hug—which showed Julian Schnabel himself counting you as one of his friends. The downside to our Pollocks and Mondrians, our de Koonings and Gorkys, was a lopsided devotion to self‑expression. From there, it was only the circumference of a white collar to notions of artistic stardom, to craving a context for the pieces we saw and owned—to the belief that art and modishness were equatable, even synonymous. Maybe this was why so many fashion moguls sought out Cindy Sherman for magazine layouts and advertising spreads. What were these commissions if not celebrity endorsements geared toward the Upper East Side? Sherman's work must have been particularly appealing since it was wholly comprised of self‑portraits—photographic ones at that. Here was a convenient fusion of art and artist, of a luminary and the mechanisms of her illumination. Or was it?

It's a question you can answer yourself, thanks to a Cindy Sherman retrospective that's currently on a limping, lolling tour of the planet earth. Organized by Chicago's Museum of Contemporary Art and the Museum of Contemporary Art, Los Angeles, it will see seven cities, six countries and a new millennium before all is said and done. Included are 151 photographs taken by Sherman over a twenty year period, so any dawdling it does is out of necessity. This isn't the sort of exhibit you breeze through in an hour. In fact, if you can pry yourself away from a single image in less than fifteen minutes, you win.

I write this in all seriousness. That so much effort has gone into discovering Sherman's true identity should indicate just how two‑faced (ten‑faced, twenty‑faced) the woman really is. Most of the images are closely cropped and in extreme close‑up, and yet you can't get an accurate fix even on the color of her eyes. Her head is at once narrow and as broad as a serving platter, the shape of her mouth fluctuates between a prim little slit and the gaping maw of a seductress, and her nose has more alter egos than Sibyl. And it's not as if you can't locate those features which were prosthetically enhanced; she's all seams and zippers, the camouflaged equivalent of a man in a monkey suit. Therefore, the transformations take place somewhere else, perhaps internally or between the lenses of the camera.

Born in New Jersey and raised in suburban Long Island, Sherman had a rather inauspicious start in her field. While studying painting at State University College in Buffalo, New York, she took a requisite course in photography which she promptly failed. It's an anecdote—similar to the one about Michael Jordan being cut from the varsity basketball team in high school—perpetuated by budding artists to convince themselves that their mediocre talent is merely the first stop on the road to fame and fortune. But what these students fail to realize is that, like Jordan, Sherman had the head but not yet the skills for the career ahead of her. It was the technical aspects of making a print that stumped her, not the aesthetics. Sherman's second photography teacher introduced her to conceptual art, a variation on the medium—as pioneered by the likes of Adrian Piper and Eleanor Antin—that meshed nicely with her realistic paintings of magazine images. Her first successful foray in this direction was a series of photographs (Untitled A‑E, 1975) that explored the elasticity of her own face. They can't be called self‑portraits because they bear no resemblance at all to the young Sherman. Included in the retrospective by way of introduction only, they are the origins of a life‑long obsession with female archetypes.

The most charming thing about these photographs are the visible tan lines which trace out the inverse silhouette of a bikini or halter top. It's comforting to know that the author of the subsequent freak show was normal enough, at one time at least, to concern herself with something so prosaic as a sunburn. Figure A shows Sherman as a middle‑aged Floridian, cherry‑lipped and demure in a beach hat and thickly applied eyeliner. In Figure B, she has her shoulders pulled back to mimic the physique of a man, a railroad cap and false eyebrows rounding out the illusion. And in Figures C‑E, she's a ball‑nosed ballerina, a homely child and a sleepy‑eyed sophisticate, respectively. All five photographs demonstrate an intuitive grasp of human nature, of the attitudes and self‑conceptualizing that go into a person's physical attributes. A visage is the product of one's interior life, they seem to be saying. We are what we think we are.

Playing dress‑up proved addictive. Sherman soon found herself loitering within thrift stores, making impulsive purchases whenever a new idea struck her. "So it just grew and grew until I was buying and collecting more and more of these things," she told the journal Art Papers in 1995, "and suddenly the characters came together just because I had so much of the detritus from them." She even wore these costumes to parties and gallery openings, the belle of her own masquerade ball. After graduation in 1977, Sherman moved to New York City where she embarked on a three year project whose purpose was to call Hollywood on its female stereotypes. These Untitled Film Stills featured Sherman once again, this time as familiar but unidentifiable movie heroines. Each of the sixty‑nine pictures catches Sherman in acts of composed spontaneity. They're not unlike the hazy cover images of a supermarket tabloid, those intrusive celebrity pot‑shots that are both candid and compromising, but also retain some semblance of their subject's allure. In one of these stills (#54), she's a dead ringer for Marilyn Monroe—a rare instance when Sherman actually shows her hand. The rest of the pictures are composites and the most effective of those in the artist's vast oeuvre.

Sherman concluded these experiments when she realized she was duplicating stereotypes. From here, her work took a decidedly nihilistic turn. When asked in 1981 to create a portfolio for Artforum magazine, she responded with Horizontals, a clothed modification of pornographic centerfolds that had her looking like a rape victim or, at the very least, someone who had made a rough night of it. The point of this series was to mimic the poses found in Playboy or Penthouse, only without the payoff. But I have to agree with Artforum's decision to reject these pictures. They aren't as intriguing or subtle as the film stills, nor are they satirical enough to completely diffuse the sexual aura which wafts from them like day‑old perfume. Calvin Klein has made a killing proffering similar images, if that tells you anything.

The same can be said of her Fashion portraits (1983, 1984, 1993, 1994) which were commissioned by Interview magazine and Harper's Bizarre. In these, Sherman is the butt of someone's cruel joke, a homeless woman plucked from the streets and forced into designer duds that are ill‑fitting and clash violently with the grime in her fingernails, in her hair. They were to be the antithesis of the typical fashion layout, a commentary on conformity and mass consumption. Exactly how Sherman planned to navigate the fact that they were, by their very nature, also advertisements for lines of clothing remains a mystery. In any event, the photographs were ground‑breaking if for no other reason than that they subverted traditional notions of beauty and femininity.

Nihilism gives way to downright profanity as we approach the '90s. These later works, particularly those labeled Disasters (1986‑89) and Fairy Tales (1985), are lessons in morbidity. It was at this point that Sherman plunged headlong into every sort of taboo and inborn fear imaginable. The dusty remnants of a nuclear holocaust approximate the splayed limbs of what looks to be an unlucky office secretary. A child weeps over a piggish snout which resulted, we can only assume, from a run‑in with a disgruntled sorcerer. Incorporating dramatic lighting, flamboyant costumes, prostheses, wigs, and all manner of prop and backdrop, such photographs show Sherman, the subject, slowly dissolving into an artifice of her own creation. It's as if she were depicting the human form from the inside out, forcing the anguish of her previous pictures through pores as wide and ugly as a gunshot wound. This new track served Sherman well. It realized its Surrealist inheritance without succumbing to the movement's romanticism. Its dark humor made us laugh nervously in the face of our own bodily frailty.

This was not the case with the string of works completed in 1992. In the Sex Pictures, Sherman was finally replaced by a collection of mannequins which were arranged in unlikely heaps that recalled sexual positions and configurations too ambitious to be attempted at home. Done in part as a response to the obscenity and censorship debates that kicked off the decade, this work is shoddy, transparent and, due to its blatant disregard for the rudiments of good taste, a bit heavy‑handed for even the most seasoned of museum attendees.

No, Sherman was at her best when she was teasing us with her ears and neck, the only parts of her we knew to be valid—original. For it was then that her images possessed us with their elusiveness, their guile. Much to the chagrin of her star‑hungry public, it turned out that none of Sherman's many portraits were extensions of her own personality. Unlike her Surrealist forbearers, not to mention the Abstract Expressionists, Sherman had reference points everywhere except within. Hers was a societal art, one that reflected and accentuated but never revealed its source. In fact, she prefers not being photographed as her ordinary self and will avoid an interview if at all possible—quirks that made her a frustrating anomaly at the height of her popularity. Unfortunately, this retrospective comes during a period in art history that thinks it has seen it all, that's plagued by indirection and a veritable potluck of influence and style. Most artists don't care who they are, let alone who Cindy Sherman is. So in this sense, her work relies on a context for its potency as much as Kandinski's ever did. It's a good exhibit, maybe even a great one, but how much better it could have been had it taken its leisurely walk through 1988 when artistic celebrity was king and Cindy was nowhere to be found.