SEASON 1, EPISODE 103 | AIRED ON 09/04/12

Moment 16: Oprah and Gayle's Big Adventure

Oprah says it was one of the craziest things she's ever done. In 2006, Oprah decided to see the USA in a Chevrolet with her best friend, Gayle King, and drive from her Santa Barbara home to New York City for the Tony Awards. Their 10-day, 3,600-mile journey delighted viewers—but it ended up being an experience Oprah would rather forget!

Why TV Guide Magazine loved this moment