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Season 21: "Oprah and Gayle's Big Adventure, Part 1"
After her landmark 20th season, Oprah had a summer vacation she'll never forget: She embarked on a cross-country road trip with her best friend Gayle. They saw the USA in a Chevrolet, driving from Santa Barbara, California, to New York City just in time for the Tony Awards, where The Color Purple was nominated. "It was one of the craziest things I've ever done," she said.

On September 18, 2006, the first of a five-part series chronicling 10 days and 36,000 miles on the road aired. Along the way, Oprah and Gayle impersonated themselves at an impersonation convention in Vegas, visited the Amish and even crashed a wedding. "Just seeing people live their lives to the best of their ability—the cowboys in Oklahoma and the weddings that we were able to crash. I loved seeing how America really lives. I love the country, and what I realized is it doesn't matter where you live, it doesn't matter how you live—we are all one heart."

Look back at Oprah and Gayle's Big Adventure


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