Original Airdate: September 11, 2019

Oprah talks to Cybill Shepherd, Ali MacGraw, Beverly Johnson, Jamie Lee Curtis and Bo Derek about what it's like to age in the spotlight. In a candid conversation, Cybill Shepherd reveals that her model looks opened doors for her and also discusses the moment she realized that heads were no longer turning her way. Oprah also sits down with ‘70s icon Ali MacGraw to talk about how she's learned to embrace getting older, as well as what it was like for her to realize she was not the "it girl" any more. Supermodel Beverly Johnson shares the moment she realized she should stop trying to look like a younger woman and Jamie Lee Curtis discusses why aging has finally given her freedom. Bo Derek reveals why getting older makes her better.