January 14, 2014
Oprah and Gayle. Gayle and Oprah. The relationship of best friends played out in front of millions when they decided to drive cross-country by themselves (of course, with a camera crew in tow). The trip started in Santa Barbara and ended 10 days and 3,600 miles later in New York City, with stops at the Wynn Hotel in Las Vegas, a Navajo reservation, two weddings, a Dairy Queen, Graceland, the Lorraine Motel (where Martin Luther King Jr. was slain), Amish country in Pennsylvania and more. Despite Gayle's constant singing, the duo remained close friends afterward, fulfilling the pinkie swear they made at the beginning of the trip and participating in myriad experiences.