25 Years of Oprah and Gayle on The Oprah Show
Today, Oprah Winfrey and Gayle King have one of the most iconic friendships in pop culture history. Like Oprah, Gayle works in the media industry, hosting The Gayle King Show on OWN and on Oprah Radio. On top of being the original Oprah Show Ultimate Viewer, Gayle has been on the show 139 times—that's more than anyone except Oprah!
Look back at 25 years of Oprah and Gayle on The Oprah Show
Gayle flew out to Chicago—with 9-month-old daughter Kirby in tow—and had a front-row seat at an Oprah Show taping. In between the show taping and playing with Kirby, Gayle interviewed Oprah about her newfound fame and where she saw her career heading.
Watch footage from Gayle's 1987 trip to Chicago
Even then, people were curious about Oprah's plans for the future—and Gayle was no exception. When Gayle asked her best friend how much longer The Oprah Show would be on the air, Oprah told her just four more years! "I love doing the show, but I'm tired. I'm not tired of doing the show, but if I could just have a day off, I'd be thrilled. So I'm going to do it for as long as it still feels good to me, which will be for a while," Oprah said at the time.
Look back on their road trip!
Gayle: Would you rather urinate though your nose or smell things with your genitalia? I think I might have to urinate though my nose. They're both bad...
Oprah: I'm not playing this game, Gayle.
Oprah has said on several occasions that their road trip was the worst experience of her life, but Gayle wants her to clarify once and for all that it had nothing to do with her. "No, it didn't have anything to do with you," Oprah says to Gayle. "I thought we'd be stopping at lovely little bed-and-breakfasts; I thought we'd wake up in the morning and somebody would have nice little muffins there. And it turned out to be an 11-day [trip] to get to the next thing, and you're on the interstate—you can't take the scenic route."
Look back at this hilarious Oprah Show moment!
"I love Oprah saying 'my brain will be disrupted,'" Gayle says. "I was the type that was writing '2 good 2 be 4-gotten.'"
Watch Stedman talk about Oprah and Gayle's friendship
"What's made their friendship so successful is they both love to talk," he says. "So they made a pretty good living out of talking, and they're interested in the same things. They basically are sisters." Stedman also says that Gayle is like family to him and Oprah, and he's glad Oprah has such a good friend.
"Someone was just asking me the other day, 'Do you and Stedman get along?' And I said, 'Very, very, very well,'" Gayle says. "I mean, there's really nobody like him."
Look back on their trip back in time
During their stay in the colony, Oprah and Gayle battled with mice, cooking over an open fire and the dreaded task of using leaves for toilet paper. While Gayle didn't like "roughing it," Oprah says it was one of her favorite experiences of all time. "I love this better than even the road trip," she says.
It all started in 2006 when Gayle read a top 20 list of the best burgers in America, and she was determined to try to sink her teeth into as many as she could. Gayle's food tours continued after that as she traveled from Nevada to North Carolina sampling America's best pizza, sandwiches and cake.
Watch Oprah and Gayle tell one of their most hilarious food stories!
Watch Gayle's dream come true
It seemed like a normal workday for Gayle, who is the editor-at-large for O, The Oprah Magazine. The plan was for Oprah to call Gayle to make sure she was in her office when Josh arrived, but Gayle unexpectedly called Oprah first to talk about—who else—Josh Groban! "His voice does something to me," Gayle said. "I just feel him!"
While Gayle sang some of her favorite lyrics into the phone, Josh walked into her office holding a bouquet of yellow roses. "Oh my goodness!" she screamed. "Josh is here!"
"That was so much fun because Gayle has always been my biggest fan and greatest cheerleader and has always wanted the best [for me], because that's what besties do!" Oprah says.
Watch Gayle try to conquer her fears
Oprah couldn't help but get in some laughs as Gayle struggled with wanting to let go. "It's going to feel like a roller coaster, that's all!" Oprah said. "I hate roller coasters!" Gayle said. Eventually, with Oprah's encouragement, Gayle finally let go—and took off flying!
Look back on all of Oprah and Gayle's great adventures