We may be a little biased here at Oprah Daily, but Oprah and Gayle are our absolute favorite celebrity best friends.
The pair’s close-knit relationship is legendary, with fans often dubbing their own besties the “Gayle to their Oprah” and vice versa. The women themselves even marvel at their story.
While Oprah grew up impoverished, often moving between her parents’ homes in Nashville and Milwaukee, Gayle spent part of her childhood in Turkey, where she had a housekeeper and a swimming pool. But despite their vastly different upbringings, the women found one another and never looked back.
“Something about this relationship feels otherworldly to me, like it was designed by a power and a hand greater than my own,” Oprah said in the August 2006 issue of O, The Oprah Magazine. “Whatever this friendship is, it’s been a very fun ride—and we’ve taken it together.”
To celebrate these forever friends, we’ve put together a timeline of some of Gayle and Oprah’s standout moments—from their initial meeting in the 1970s to more recent updates, like when Gayle shared the sweet story of her diamond necklace from Oprah on Watch What Happens Live in December 2022.
1976: Oprah and Gayle first meet as young journalists.
They were twenty-somethings in the early days of their careers, both employed at Baltimore's WJZ station. Oprah, now 68, was an anchor for the 6 o’clock news, and Gayle, now 67, was a production assistant. Despite working in different departments, both were around the same age and single young Black women. The two struck up an immediate bond.
In the August 2006 issue of O, The Oprah Magazine, the two recounted their friendship origin story. Lady O invited Gayle to stay with her for the night after Gayle couldn’t make it home during a snowstorm. And as they say, the rest is history.
“We became friends that first night because for the first time, I met somebody who I felt was like me,” Gayle said. “I’d never met anybody like that. Certainly not another Black girl. I grew up in an all-white community.”
The two explained that both of them could relate to the fact that even their musical tastes put them at odds with peers. Gayle loved Barry Manilow, and Oprah was a fan of Neil Diamond.
“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,” Oprah said.
Gayle added: “But we still had a very strong sense of being Black and were very proud of being Black. So to meet another Black girl like that was, wow!”
1986: Gayle makes her first appearance on The Oprah Winfrey Show.
During the debut season of the iconic The Oprah Winfrey Show, Gayle made her first of many guest cameos over the years. Apparently, the episode’s topic was about celebrities and their best friends (fitting, huh?), and the duo spent the show entertaining each other by “recounting stories about ill-fitting dresses and disastrous hairdos.”
1994: Gayle surprises Oprah for her 40th birthday.
In one of our favorite moments from The Oprah Winfrey Show archives, Gayle pulled off the ultimate surprise by unexpectedly popping in on Oprah in the middle of an episode.
For an on-air party for her milestone birthday, celebrity guests like Gladys Knight, Phylicia Rashad, Aretha Franklin, and Patti LaBelle were all in attendance, talking about how they lived their best lives in their 40s. But just as Knight was providing some wisdom, a clearly shocked Oprah interrupted to make a special announcement: “Gayle is here!” she exclaimed.
The two embraced, and through tears, she explained why exactly her bestie’s appearance was so welcome.
“This is so touching to me, because Patti was here and Aretha came, and then everyone was coming, I thought, Gee, I wish Gayle could be here to see this,” she said.
Gayle was equally grateful to be in attendance, offering the most humble response. “I have no song to sing,” she said. “I have no words of wisdom. I just wanted to be here with you today.”
The. Best.
2004: Gayle and Oprah throw it back to colonial times on The Oprah Winfrey Show.
For the ultimate exercise in stepping out of their comfort zones, the duo visited a family in Maine for the PBS series Colonial House, where people live like it’s 1628. (Yes, voluntarily). It would become one of the show’s most unforgettable segments.
With no technology, running water, or electricity, Oprah and Gayle set out to spend a weekend as the colonials did—traditional garb and all. The two made a valiant attempt to survive the experience, participating in a bonfire dance in lieu of more modern entertainment. Oprah even recalled Gayle’s hilarious moves, bursting into laughter as she told the story.
“Her partner threw her down, and she falls to the ground,” Oprah said through giggles. “She forgets to make the turn—flung her a little too far there, fella.”
Later on, the friends bonded with their host family as the group all worked together to cook dinner and bake a cake. It was an experience Oprah called “one of the most special meals” she’d ever had, as it reminded her of her childhood. However, it wasn’t quite enough to convince them to live the colonial life.
“The whole idea of this experience was that we were going to spend the weekend with all of these lovely people,” Oprah said. “After Gayle got thrown down in the square-dancing episode the night before—the guy went do-si-do, and she went down—we decided to leave a little early.”
Well, at least they tried.
2006: Our resident besties set out on a grand cross-country road trip.
In a fan-favorite Oprah Winfrey Show episode, Oprah and Gayle escaped on the ultimate road trip. Dubbed “See the U.S.A. in a Chevrolet,” the two set out on an 11-day, 3,600-mile adventure from Santa Barbara to New York City.
In one exceptional clip from day two, they had been driving for hours in Arizona, and the close quarters were getting to them.
“All you had to do today was listen to my singing, which should have been very pleasurable,” Gayle said as Oprah complained about the trip.
“That’s why I’m so damn cranky,” Oprah countered.
That’s when the CBS This Morning host shot back with a little sass. “I’ve been driving for six hours. All she’s had to do was sit here and relax, and she’s bitching.”
See? Even Oprah and Gayle have fights. The mood lightened considerably hours later when the two women found themselves rooms at a motel with 55-year-old teepees. During the trip they also played bingo, met some cowboys, and even crashed a wedding. To sum it all up in one word: epic.
2018: Oprah and Gayle support each other at career-defining moments.
Both media legends in their own right—Oprah is a billionaire business mogul, and Gayle is an Emmy-winning journalist and member of the Broadcasting and Cable Hall of Fame—each of these BFFs had a banner year in 2018.
First up was Lady O in January. With words heard around the world, she accepted her Cecile B. DeMille Award at the Golden Globes with a roaring speech that sparked #Oprah2020 presidential race rumors. Along with Oprah’s partner, Stedman, Gayle was also Oprah’s date that night. Oprah even took to Instagram to show us a glimpse of their glam session, in which she poked fun at her friend’s lack of moisturizer.
“Get your elbows,” she told Gayle. “Hey, a little Ash Wednesday on the elbows, there.”
In June, for a segment on CBS This Morning, Gayle joined Oprah for a first peek at Lady O’s new exhibit at the National Museum of African American History and Culture, which showcased Oprah’s monumental life and career.
And four months later, the tables were turned when Gayle took the spotlight as she was officially inducted into the Broadcasting & Cable (B&C) Hall of Fame. Oprah presented her friend the award at the ceremony with a heartfelt toast.
“She deserves to be celebrated, not just for her news acumen, but for being her consistently joyful, vibrant, best-outlook-on-life, best-outlook-on-everybody self,” Oprah said. “We are here tonight to celebrate you for continuing to build a legacy in the space of nice. We are here to honor your curiosity, we are here to honor your inquisitive interest in all of humankind. We’re here to honor your desire to know the truth.”
January 2019: The OG Chronicles is born.
In a move that was long overdue for the dynamic duo, a joint video series was officially launched, called The OG Chronicles, starring Oprah and Gayle. (See what we did there?)
For the show, the two share the small screen as they dish out advice for their fans. As they comment on love lives and friendships, we’re also treated to some super-fun personal stories from the BFFs. In the first episode, we learned that Gayle once donned Saran wrap and a trench coat to spice up a relationship, while Oprah cooks soul food to keep it romantic with Stedman.
“I made some cornbread yesterday, and you would have thought I stripped myself butt naked,” she revealed.
One thing that’s obvious? We’ll never get tired of these women and their long-lasting friendship. It’s clear that they have a bond like nothing else, and it’s beautiful to see. So what’s their secret?
“When we first met, Gayle was always very happy with her life,” Oprah said. “And, therefore, happiest for my life... You cannot have a friend that’s unhappy with their life be happy with your life. You’ve gotta have happiness to give happiness to other people.”
March 2019: Oprah praises Gayle for her contentious R. Kelly interview.
Following Lifetime’s explosive Surviving R. Kelly documentary, the disgraced artist sat down with Gayle in his first interview since he was arrested in Chicago on 10 counts of aggravated criminal sexual abuse.
The explosive segment garnered Gayle widespread praise as she kept her cool while Kelly proceeded to lose his. And one person who was in her corner during her glowing show of professionalism? Her bestie, Oprah, of course.
“Bravo @GayleKing for calm and steady focus during #RKelly interview. Outstanding job! Tell @CBSThis Morning we want to see the whole thing,” Winfrey tweeted.
April 2019: Oprah recognizes Gayle’s big Time magazine honor.
Just over a month later, Gayle’s hard work was put on display again when she was named one Time’s 100 Most Influential People of 2019.
“It feels surreal & WONDERFUL to not only be included #time100 list but to make one of the covers,” the honoree wrote on Instagram. “Wow! thank YOU @ava for a tribute that moved me tears .. to @cbsthismorning team who cheers me on ..to @eneida821 & @laz2020 who killed it on hair & make up, & photographer @paridukovic who said he had the perfect photo. Thinkin’ I’ll get extra copies of @ @TIME this week .. thanx time editors!!!”
And it should come as no surprise that Lady O was right there to support her again—just as they have always done in the past 45 years.
“So proud of you @GayleKing! And you @ava for capturing the spirit of her in your words. #Time100.”
So simple, but oh-so-sweet.
March 2020: Oprah interviews Gayle for the first time.
In Denver, during the last leg of Oprah’s WW 2020 Vision Tour, Gayle was interviewed by Oprah for the first time ever in their decades-long friendship. The two covered a lot of ground during their conversation, including the story of how they first met (which we detail above), Gayle’s divorce, and internet trolls. But they ended on a sentimental note about their friendship.
“The secret to me is trust. I trust you totally, even if I disagree with you, I still trust you,” Gayle said. “I have this joke with Oprah where people say, I found my best friend with my husband...I say to Oprah, ‘If you ever walked in and caught me with Stedman, you should not be mad, you should take me to the mental institution. Don’t be mad, I need help!’ But I mean, we’re honest with each other and trust each other and actually are very like-minded.”
June 2020: Oprah and Gayle reunite after quarantining separately.
After months of living on opposite coasts—Gayle in New York and Oprah in California—Gayle joined Oprah at her Santa Barbara home for a socially distanced lunch. In the days following, Oprah proved to be an excellent host, delivering ice cream to Gayle’s doorstep, who was staying in her guest house.
But after quarantining for 13 days, Oprah and Gayle finally reunited with a hug after the latter tested negative for Covid-19.
September 2021: Gayle becomes a grandmother—and Oprah becomes a grand-godparent.
Gayle’s daughter, Kirby Bumpus, and Kirby’s husband, Virgil Miller, welcomed their first child, Luca Lynn Miller, in 2021. Gayle announced the arrival on CBS Mornings, saying, “I’ve wanted to be a grandmother for a long time, and it’s really something when you see your own child become a parent.” Gayle also later revealed her special nickname for Luca on The Late Show with Stephen Colbert. “I have a little song,” Gayle said, clearing her throat. “Luca-uke-lele, what a pretty baby!”
Since Oprah is such an important part of Gayle’s life, it’s only natural that she has a role in Kirby and Luca’s lives, too. During Christmas 2021, Oprah finally met the newest addition to the family. “That is a beautiful baby,” she told her goddaughter, Kirby.
April 2022: People magazine honors Gayle and Oprah’s decades-long friendship.
Nearly 50 years after they first met, the dynamic duo’s friendship was celebrated in People’s Beautiful Issue 2022. Along with pairs like Octavia Spencer and Allison Janney, Sarah Paulson and Amanda Peet, and Mandy Moore and Minka Kelly, Oprah and Gayle got glammed up for shoot with a photographer they know and love, Joe Pugliese, who also captured Kirby’s wedding.
This was only the second time Oprah and Gayle had done a professional shoot together—the first was for the cover of O, The Oprah Magazine, in September 2019. At the People photo shoot, the pair joked around while working with a movement coordinator, Steven Galloway. Gayle even suggested Oprah should slide down into the splits—but they opted for some classic power poses instead. Check out all the behind-the-scenes moments here.
December 2022: Gayle reveals the sweetest gift Oprah has ever given her.
During an appearance on Watch What Happens Live, Gayle explained the story behind the heart-shaped diamond necklace she wears almost all the time. Turns out, the charm came from a pair of earrings Oprah had. “One day your heart will sing, from your heart to mine,” Oprah told Gayle when she gave her the gift. It was even more significant because Gayle was going through a particularly difficult time—she was on the heels of her divorce—and Oprah’s support meant the world.
March 2024: Gayle celebrates their friendship in interview with Newsweek.
Oprah Daily’s editor at large recently sat down with Newsweek to chat about CBS Mornings, King Charles, and more. While most of the interview focused on Gayle’s prolific career in journalism, her and Oprah’s friendship is so iconic that it’d be hard not to bring it up—and the interviewer even noted that Gayle “must get asked about her all the time.” He clarified, “Do you, and is there something you’re sick of being asked about?”
Gayle replied, “I never get sick of being asked about Oprah because I so love that she is loved the way she is. I so love that she is embraced the way she is. And it only makes me proud.”
She continued, “I feel about Oprah the way I feel about [my] favorite son, Will, and [my] favorite daughter, Kirby, that I can’t wait for people to meet them because they never disappoint me. So anytime someone gets to meet her or wants to ask me something about her, I don’t have the hang-up, Oh, God, I wish they’d stop asking me about Oprah. Because I don’t. You would only feel that way if—and I’ve said this before—I don’t see myself in her shadow. I see myself in her light. So anytime somebody says something about her to me, I am never offended by that ever.”
McKenzie Jean-Philippe is the editorial assistant at OprahMag.com covering pop culture, TV, movies, celebrity, and lifestyle. She loves a great Oprah viral moment and all things Netflix—but come summertime, Big Brother has her heart. On a day off you'll find her curled up with a new juicy romance novel.
