“Tell me what to do,” Cindy Sherman said, asking the photographer for guidance as she sat for her portrait. Her words seem almost comic, since she is posing in her own New York studio, staring out at her camera and the mirror she keeps perched beside it, and the one thing she has proved, across a career that turned 40 this year, is that she has known what to “do” in this setting.

She has used that camera and mirror to capture herself playing a vamp and a secretary, a starlet and a matron, a corpse and a clown and other iconic roles our culture has cast women in. Now, after a sabbatical from the studio “coming to terms with health issues and getting older,” Ms. Sherman, 62, has produced her first new photos in five years. They are more explicitly about herself than ever before — images that confront what aging means to a woman. In the series, which starts May 5 at Metro Pictures gallery in New York, she plays the veteran leading ladies of cinema’s Golden Age, turning herself into avatars of Gloria Swanson, Greta Garbo and others in their twilight years. “I relate so much to these women,” she said. “They look like they’ve been through a lot, and they’re survivors. And you can see some of the pain in there, but they’re looking forward and moving on.”