12 Throwback Photos of Oprah & Gayle — and the Friendship Lessons They've Taught Us

Their enduring bond serves as an inspiration for us all

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You’re Never Too Old for a Slumber Party

Winfrey and King’s storied friendship all began one snowy Baltimore evening when the future talk show host invited King to stay the night. Winfrey and King — who worked together at the same news station as an anchor and production assistant, respectively — spent all night chatting. “We didn’t really know each other,” King said of the fateful night, “but she was just that kind of girl even then. When I said didn’t have any clothes with me, she said, ‘You can wear mine,’ and when I said I didn’t have any underwear she said, ‘You can borrow mine, it’s clean!’ ” And the rest, as they say, is history.

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Be Your BFF’s Biggest Cheerleader…

When Winfrey was in the midst of changing jobs early on in their friendship, everyone in her circle seemed to be against the move — except for King. “Gayle was the only one who said ‘I think you can do it!’ “

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…Unless You Need to Be Brutally Honest About Her Style

Because a real friend doesn’t let her BFF look less than stellar on TV. King once appeared on the CBS Morning Show wearing an emerald top with a blingy, oversized, bib-style necklace — a look Winfrey wasn’t too fond of. Apparently, the media mogul sent a note to King’s assistant that morning saying, “plz tell Gayle I’m on treadmill & it’s hard to focus w/ the circus around your neck.” King’s response? “I think she’s WRONG.” (Oprah has also sent notes on Gayle’s lipstick choices – but hey, at least she’s watching!)

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You Can’t Put a Price on True Friendship

“When she was making $50 an hour, I was making $27. Somebody said, ‘Do you ever feel lesser?’ ” King recounted as a guest on Winfrey’s talk show. “And I go, ‘No, it’s not a friendship based on money.’ I never feel like I’m competing. I never feel lesser than.”

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Your Soulmate Better Love Your BFF Too

“Gayle is someone I care for and she’s family … I care so much for and respect so much of who both of [them] are and I’m glad [they] are great friends,” Winfrey’s longtime love, Stedman Graham, said in an interview. “I love it. I just think it’s wonderful. I hope [they’re] friends forever.” (Searching for your own Stedman? You’ll probably want to watch Oprah and Gayle’s series of relationship advice videos.)

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It’s Normal to Squabble About the Small Stuff

“I’m not big on birthdays, she is,” Winfrey told her studio audience of King. “Some of our biggest fights have been about birthdays.” (And if you know it’s a pain point, set rules ahead of time: Oprah and Gayle no longer exchange Christmas gifts because “we don’t really need anything.”)

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Be Open About Your Feelings

Despite being inseparable, Winfrey emotionally revealed in a 2010 interview with Barbara Walters that she hadn’t succeeded in telling King how much she appreciates their longstanding friendship. “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. I don’t know a better person,” Winfrey said, through tears. “It’s making me cry because I’m thinking about … how much … I probably have never told her that.” 

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Remember: If She Knows All Your Secrets, One Might Slip!

Ever wondered what Oprah does when she wants to let loose? Let Gayle reveal all: “Oprah has smoked a little marijuana too, I don’t mind saying. I’m not telling tales out of school,” she told Ellen DeGeneres. Care to elaborate, Gayle? “I refuse to answer on the grounds that it may incriminate her!”

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Priortize Experiences with Each Other

You learn a lot about a person while traveling. For Winfrey and King, the adage rang true during their two-day, 3,600-mile road trip together — which was all documented for Winfrey’s hit talk show. “When you’ve been on the road for a long period of time, you just get absolutely silly for no reason,” King said of their time together, over a montage of the famous friends goofing off at a store.

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Be There for Each Other in the Hard Times

Winfrey and King spent New Year’s Eve in 2014 at Kula Hospital in Maui after King sprained her ankle during the twosome’s Hawaiian vacation. To ensure a memorable time for the BFFs, Winfrey flew in King’s family to the resort, where they all rang in the new year together.

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Find Any Excuse to Hang Out Together

What’s better than a tropical vacation with your BFF? Getting paid to go on a tropical vacation with your BFF! Oprah and Gayle headed out with 2,600 of their closest friends on a three-day “Girls’ Getaway” trip on Holland America’s Nieuw Statendam in January 2019, the day after Oprah turned 65.

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Show Up — Literally

In a June 2019 interview with PEOPLE, Gayle told the story of her first New Year’s Eve post-divorce in 1993.

“My ex was going to have the kids,” said Gayle, who was the anchor at WFSB in Hartford, Connecticut, at the time. “I was talking to Oprah on the phone that morning. And I said, ‘What are you guys doing?’ And, she told me something.”

Preparing to spend night alone, King was shocked when “four hours later, the doorbell rang and she and Stedman [Graham] were at the door,” she says. “She had been planning to come. I didn’t know that … I just kept saying, ‘I can’t believe you guys were here.’ That was something that I’ll never, ever, ever forget.”

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