The Stunning Transformation Of Oprah & Gayle

It's the fascinating tale of the world's most influential self-made mogul, and her ride or die. And no, we're not talking about Stedman. "She is the mother I never had. She is the sister everybody would want. She is the friend that everybody deserves. I don't know a better person," Oprah has said of Gayle. And according to Gayle, the feeling is mutual, "Who doesn't want to be her best friend? I never feel I'm in her shadow. I feel I'm in her light, that's how I look at it."

In the most sensational rags-to-riches story ever told, Oprah Winfrey rose from devastating poverty to the very top of a $2.9 billion empire, with BFF Gayle King by her side all the way. A fateful snowstorm brought the two together when they were just 20 and 21, and they quickly realized they were more than just "work friends". "[It's] the night I wore Oprah's underwear," Gayle joked, of the sleepover that would bond them for life in 1976. Now in their 60s, the two media mavens rock matching Bentleys, twinsie jammies, and a mutually profound respect for each other. And after 40 years spent sharing everything together, the question remains: Are they or aren't they more than friends? Spoiler: they're more than just regular BFFs, but not in that way.

A whip-smart, teenaged fan of Neil Diamond, Oprah commiserated over the difficulties she faced in school: "It's that whole being-the-odd-girl-out thing — we didn't fit in to everybody else's perception of what it's like to be a black girl." Gayle added, "I grew up in an all-white community. I remember getting embarrassed in fourth grade when a boy in my class named Wayne said, 'If it weren't for Abraham Lincoln, you'd be my slave.'"

A devastating home life, as well as sexual abuse by family members, forced Oprah to run to the streets, resulting in a pregnancy at just 14 years old. Immediately sent to live with her strict father, she hid her pregnancy until the day she went into labor. A premature baby boy was born and later died. "My father said to me, 'This is your second chance'," Oprah shared with Makers.

They've told the story a thousand times. Oprah was a 22-year-old co-anchor at WJZ News, making $22,000 a year. "She connected with the female audience instantly," NY Times TV critic Bill Carter remembered. "Oprah was genuine." And just steps away from the rising star, 21-year-old Gayle was working at the same station as a production assistant, banking $12,000 a year in her entry level position.

Reflecting on their shared experience as young, single, African American career women leading a shift toward diversity, Gayle admitted, "You're a pioneer, and you don't even know you're a pioneer. But... clearly it was uncharted territory." And speaking about her future best friend, "For the first time, I met somebody who I felt was like me. I'd never met anybody like that. Certainly not another black girl."

"There are some weddings you go to and you're just filled with all this hope for the couple...I didn't feel that at yours," Oprah revealed to Gayle long after Gayle had divorced her only husband, attorney William Bumpus. "But you were maid of honor!" Gayle laughed, of the wedding that took place when she was 27 years old.

But even though she wasn't feeling the love at the time, 28-year-old Oprah championed the happiness of her best friend. Even if she was struggling against her own feelings. She continued, admitting to Gayle, "Also... I felt like, well, maybe it's just me being jealous. Maybe I couldn't feel the joy because I was feeling like our friendship was going to change. But it didn't."

In one of the most speculated-about pairings of all time, Oprah struck up a relationship with the elusive Stedman Graham, 35, when she was 32 years old. Two years later, Oprah told Barbara Walters, "It would be wonderful [to marry] Stedman [but] I know I'm not ready." While the two have stayed together over 30 years, never tying the knot, Stedman did once propose to Oprah in 1992. And who else was hanging around during the impromptu moment? You guessed it — Gayle.

"The truth is, no matter where I am, whether Stedman is there or not, Gayle's in the other room," Oprah shared in O Magazine. Gayle continued, "I really do marvel at this because if Stedman didn't accept me, it would be very difficult for us to be friends." For Stedman, Gayle is a welcome part of the family: "What's made [Oprah and Gayle's] friendship so successful is they both love to talk... and they're interested in the same things," he said. "They basically are sisters."

During her marriage to William Bumpus, Gayle gave birth to her "favorite son and daughter". In 1987 daughter Kirby arrived. And almost a year later she gave birth to William Jr. Oprah wanted to give something special to the new mom. Gayle described Oprah's gift to her the best, "The kids are 11 months apart, and Oprah goes, 'I got you the perfect gift." And I'm thinking, 'Oh good. She's giving me a double stroller.' Back then double strollers were very expensive. But the gift turned out to be a nanny! She said, 'I want to pay the nanny's salary for as long as you feel you need her.'"

Now that they're all grown up, Gayle and her kids frequently vacation with Oprah. After Gayle divorced her husband in 1993, Oprah said of her friend, "I admire a lot of things about Gayle. But when I think about the way she raised her kids, that makes me weepy... It's always, always, always been about what's best for her children." She added, "Her children are my children."

With megawatt surprise guests Patti LaBelle, Aretha Franklin, Phylicia Rashad, and Stedman appearing for Oprah's birthday celebration on The Oprah Show, it's hard to imagine anyone topping the lineup. But the moment her bestie walked out from backstage, Oprah lost her cool, tearing up with a birthday tiara on her head. "I was gonna have a quiet little dinner and not make a big deal about [my 40th birthday], but..." she said.

Oprah later explained the rush of emotion, as she stood in the audience with her partner in crime, "This is so touching to me because when Patti was here and then Aretha came and everyone was coming, I thought, 'Gee, I wish Gayle could be here to see this'."

BFF Gayle, who was so famously well-adjusted to Oprah's wild success, finally hit her breaking point, when Oprah took the stage with Tina Turner on The Oprah Show in 1997. Later, Oprah recalled, "The only time [Gayle's] ever been jealous of anything — and she just said, 'I'm jealous' — was with me singing with Tina Turner. Which is so interesting because [Gayle] can't sing."

But the friendship survived Tina, and that one flash of envy, becoming stronger because of Gayle's honesty about her true feelings. But it's not the only thing Gayle has offered the relationship. "The therapy that I didn't have, and the therapy that I don't need, is because of my thousands and thousands of hours on the phone with Gayle," Oprah told Barbara Walters.

"Oh no, it's my last Oprah Show appearance, I am not wearing jeans," Gayle said, as she fixed her hair in the dressing room mirror before stepping out on stage for the last time, for Oprah's final season of the show. As Oprah, who had many shows yet to tape, reviewed her own jeans-based options, Gayle audibly disapproved, hoping for a more upscale sense of occasion. "Gayle, it's The Oprah Winfrey Show, I can wear whatever I want," Oprah expressed, with growing frustration.

But Gayle has always felt the gravity and importance of Oprah's successes, far more deeply than maybe Oprah herself. "It's one of the things that's so amazing about this friendship. Gayle is more excited about my success than I am. It makes her genuinely happy. We've made this journey together," Oprah shared in O Magazine.

"She's never asked me for a dime. There is a level of mutual respect that comes from being with somebody you know doesn't want anything from you but you," Oprah said of Gayle. "But let me just say this, too. The person who has the money has to have a generous spirit."

And she sure does. For Gayle's big 6-0, Oprah flew Gayle's entire family to Hawaii for the celebration. And when Gayle sprained her ankle walking to the gym during New Years Eve on that vacation, her best friend stayed by her side in a Maui hospital, even pushing her in a wheelchair.

Theirs is a friendship most of us can only dream of. A deeply and mutually adoring partnership. A kind of luxuriously endless sleepover. And even in their early sixties, the two mega successful media stars are just getting started. Recently, Oprah launched her 2017 Year of Adventure with a hike through the Grand Canyon — with "sister-friend" Gayle, of course. Oprah also hopes to become a master teacher, and yes, "make peace with the weight thing". And, if she can find a spare moment in between crushing it on CBS This Morning, O Magazine, and sharing her Weight Watchers journey, we're betting Gayle will be with her for all of it.

"There isn't a definition in our culture for this kind of bond between women," Oprah said of her friend. "So I get why people have to label it — how can you be this close without it being sexual? How else can you explain a level of intimacy where someone always loves you, always respects you, admires you?" Gayle added, "I think about when we get old, but I can't imagine life without Oprah. I really can't. I'll go first if I can be 90 and [Oprah] can be 91." Oprah assured, "Something about this relationship feels otherworldly to me, like it was designed by a power and a hand greater than my own. Whatever this friendship is, it's been a very fun ride—and we've taken it together."