Thirty-five years ago, Oprah was working as a news anchor in Baltimore, where she met a production assistant named Gayle. The two didn't know each other that well, but one night there was a snowstorm, and Oprah told Gayle she could stay at her home to wait it out. Gayle accepted the offer, and the two women stayed up all night talking...and they never really stopped.
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!
In 1987, Gayle was anchoring the news in Hartford, Connecticut, and Oprah was taping the second season of The Oprah Show. When Gayle needed a big story to boost ratings, her news station sent her to interview Oprah.
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.
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.
Oprah and Gayle's 11-day road trip across America was a hit with viewers everywhere, but just one hour into the trip, Oprah knew she was in trouble. That's when Gayle decided to play some car games to pass the time.
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."
In 1991, Oprah and Gayle tapped into their inner teenagers when they read their old love letters from high school on the air. The two best friends cracked each other up as they recalled their teenage days—especially when Oprah read a letter that she wrote to her first love, Anthony: "On today, June 22, 1971, I've decided to voice my thoughts on paper to prevent my brain from becoming disrupted."
"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."
Back in Season 18 of The Oprah Winfrey Show, someone came up with the brilliant idea to send Oprah and Gayle 400 years back in time to live in the colonial days. The two best friends joined 26 other people who were living in a remote "colony" in Maine reconstructing life as it was in 1628. That meant no running water, no electricity and no toilets.
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.
One of the things Oprah loves about her best friend Gayle is that she's so passionate about the two loves of her life: The first is her children, Kirby and Will, and the second is food! Over the years, Gayle has served as The Oprah Show's go-to food reporter. She has traveled from coast to coast in search of the best culinary classics.
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.
In 2005, The Oprah Show's Wildest Dreams bus toured the country, making over 100 viewers' dreams come true. When it rolled through New York City, Oprah decided to pull a fast one on Gayle by fulfilling one of her wildest dreams—meeting singer Josh Groban!
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.
In 2006, Oprah and Gayle embarked on the ultimate spa getaway with some deserving O, The Oprah Magazine contest winners. At the Miraval Resort and Spa in Tucson, Arizona, Gayle—who is afraid of heights—agreed to be hoisted 40 feet in the air for a self-improvement exercise called A Wing and a Prayer. The idea of the exercise was to get over your fears and let yourself drop in the air, all in the name of self-improvement. But there was just one problem: Gayle wouldn't let herself fall.
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!