Photograph by Luisa Dorr for TIME

Cindy Sherman

The victim, the psycho bitch, the good wife. Lady readers will know what I mean when I say we are supposed to embody these roles, but unknowingly, so as not to ruin the mood. It's this mood that Cindy Sherman's role-playing self-portraits have disrupted and repurposed over the past 40 years. Her photographs always beguile at first—She's so pretty! So sad! So crazy!—but in the next moment we remember, "She" took this picture.

She knows.

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This has never felt more subversive than in Sherman's most recent works. Rather than playing a young ingenue from a vintage film, as she often has, she portrays richly costumed older women in the 1920s, perhaps trying to imitate the starlets of the day. Sherman chases youth backward through time to create an astoundingly complex portrait of a woman in her 60s living today. This is particularly piercing in a moment when old-timey sexism has leaped from the grave with a grabbing hand. Sherman has trained us to look, and then look again more closely—not just at her, but at every image of a woman.

July is a filmmaker, artist and writer

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