It's the fascinating tale of the world's most influential self-made mogul, and her ride-or-die.
After working together in their 20s, Oprah Winfrey and Gayle King quickly realized they
were more than just "work friends" — they were best friends.
Now in their 60s, the two media mavens rock matching Bentleys, twinsie jammies, and a
mutually profound respect for each other.
Here's a look at the stunning transformation of Oprah & Gayle.
Rags and riches
Though they were born in 1954, their beginnings were starkly different.
Gayle, a Maryland native, was born to an upper-middle class family with a pool and a maid.
She even lived in Turkey from age 6 to 11, thanks to her father's engineering work.
Still, Gayle had times when she felt she didn't fit into her community, saying,
"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.
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.'"
Meanwhile, Oprah was born in Mississippi to an 18-year-old unwed mother, and faced much
harder times.
"There was no running water, no electricity and right out back here used to be an outhouse."
Winfrey was raised by her grandmother through the age of six.
Oprah revealed in an interview for Makers,
"My grandmother never imagined that I could be anything bigger than a maid.
She used to say 'I just hope you get some good white folks when you grow up'.
And I remember being about 5 years old, and I knew that I wasn't going to have that life."
Her devastating home life, as well as sexual abuse by family members, forced Oprah to run
to the streets, resulting in her becoming pregnant 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.
It was then that her father told her that this was her second chance.
And she took it.
Work friends
By 1976, Oprah was a 22-year-old co-anchor at WJZ News, making $22,000 a year.
New York Times TV critic Bill Carter remembered Oprah as genuine, and able to easily connect
with a female audience.
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.
Oprah made the first move, inviting Gayle to wait out a bad Baltimore snowstorm at her
place.
Although they had spent hours together in the newsroom every day, they weren't yet friends,
due to their very different jobs, and the hierarchy of the newsroom.
Gayle explained,
"This is something that's so unique to Oprah and really not surprising to who she is today."
As fate would have it, after borrowing clothes and chatting all night long, the two forged
the beginnings of a life-long bond.
Reflecting on their shared experience as young, single, African American career women leading
a shift toward diversity, Gayle admitted,
"I never felt like I was a pioneer.
I don't think she ever felt like she was a pioneer.
But when I look back on those days clearly it was uncharted territory."
An unhappy marriage
Oprah was the maid of honor at Gayle's 1982 wedding, but she just wasn't into her friend's
impending marriage.
To be fair, Oprah wasn't wrong — Gayle later divorced her husband when she found him in
bed with another woman.
Oprah revealed to O Magazine,
"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."
Even though she wasn't feeling the love at the time, 28-year-old Oprah championed the
happiness of her best friend while struggling against her own feelings.
Oprah admitted to possibly being jealous and being afraid that her friendship with Gayle
would change after her marriage, but fortunately for them both, everything remained the same.
Oprah hits the air
By 1986, the 32-year-old Oprah was about to hit a ratings jackpot with her morning show
on WLS-TV in Chicago, while Gayle, 31, was already establishing herself as a star anchor
on Hartford's WFSB evening broadcast.
"That's our report for tonight, thank you for joining us.
We'll all be black next, we'll all be back next week and I'll be black, we'll all be
back."
It was around then that Oprah began to publicly address her struggles with her weight, which
would become a defining element of her brand.
Oprah told Vogue,
"That's why I first brought it up on TV…
I said, 'I know y'all are thinking, Look at her fat butt.
It's a little issue I've had for a while.'
All my friends, except Gayle, told me I wouldn't get the job in Chicago because I'm black and
overweight."
Even through their individual struggles, the long-distance pals remained closer than ever,
supporting each other despite what anyone else thought.
Starting families
It was also in 1986 that Oprah struck up a relationship with the elusive Stedman Graham,
but they weren't quick to marry.
"It would be wonderful if, if it is Stedman."
"Then why don't you do it?"
"Because I know I'm not ready."
"I don't think he is, but I know I am 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.
Oprah told O Magazine,
"The truth is, no matter where I am, whether Stedman is there or not, Gayle's in the other
room."
Gayle added,
"I really do marvel at this because if Stedman didn't accept me, it would be very difficult
for us to be friends."
Stedman, for his part, isn't threatened by the friendship, and considers the pair to
be like sisters.
A year later in 1987, Gayle gave birth to her daughter Kirby, followed by William Jr.
about a year later.
Oprah wanted to give something special to the new mom, and in true Oprah style, she
blew every other shower gift out of the way by giving Gayle a fully-paid nanny for as
long as Gayle wanted.
And though Oprah has no kids of her own, she and Gayle are so close that Oprah considers
Gayle's kids to be part of her family.
The big 4-0 and beyond
Much of the duo's legendary friendship has been documented on Oprah's own show, and one
of the more telling moments was during Oprah's surprise 40th birthday celebration in 1994.
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.
"Are you really surprised?"
"Yes"
But if there was one moment that nearly broke the pair's friendship, it was when Oprah took
the stage with Tina Turner on The Oprah Show in 1997.
Later, Oprah recalled,
"The only time she has ever been jealous of anything, she just said I'm jealous."
"Which is so interesting because she can't sing."
But the friendship survived Tina, becoming stronger because of Gayle's honesty about
her true feelings.
Road trip
"Let's just add to that lesbian rumor."
"Lesbian rumors."
"Come on in, baby!"
It was the summer of Oprah's 20th season in 2006, and the two had struck out on an adventure
that would take them from Santa Barbara, CA to New York City in 10 days.
Testing the bounds of their patience, the two quickly ran into trouble, as two independent
women stuck together in a car who had never spent 11 straight days in close proximity
to each other.
"I had to sit here for six hours and take in other peoples energy."
"She's just cranky and bitching and getting old and Oprah and nobody cares because we
are all friggin tired."
Cameras rolled as they hashed out their own rules of the road, who picks the music, and
played "Would You Rather".
And with their fair share of hiccups, and grungy motels, the two made it to NYC in one
piece.
"I'm really Oprah, I really am."
"No you are not."
"Yes I am, I am."
Surprising at 60
In 2014, Oprah decided to throw a massive early 60th birthday bash for her BFF, made
possible by the O Magazine staff.
The theme?
"The world according to Gayle," which included Gayle's closest friends and family wearing
her favorite color — yellow — and her favorite shoes — clogs.
Along with bright yellow balloons and smiles all around, there were 960 cupcakes, custom
grilled cheese sandwiches, and burgers from Shake Shack.
Gayle praised her friend's thoughtful generosity, sharing,
"Oprah always says this — that 'love is in the details' — and I certainly felt that."
In addition to all of that, Oprah flew Gayle's entire family to Hawaii for the celebration.
And when Gayle sprained her ankle walking to the gym during New Year's Eve during her
vacation, her best friend stayed by her side in a Maui hospital, even pushing her in a
wheelchair.
Still going strong
Theirs is a friendship most of us can only dream of: a kind of luxuriously endless sleepover.
And even in their early sixties, the two mega successful media stars are just getting started.
Oprah launched her 2017 Year of Adventure with a hike through the Grand Canyon, with
"sister-friend" Gayle, of course.
In an interview with O Magazine, Gayle said,
"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 has also reflected on their enduring friendship.
"She is the friend that everybody deserves.
I don't know a better person."
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