Revisiting the heyday of department stores and five-and-dimes

No. 420: Oprah Winfrey, 57, Chicago, television, $2.7B

Oprah Winfrey waves to her fans in September while taping an episode of "The Oprah Winfrey Show" on Michigan Avenue to kick off the show's 24th season in 2009. (Kiichiro Sato/AP)
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