Oprah Winfrey and Gayle King’s best memories photos and friendship quotes

You’re never too old for a slumber party

Winfrey and King’s legendary friendship began one snowy night in Baltimore when the future talk show host invited King over to his house and they chatted all night.

“We didn’t really know each other,” King said of that fateful night. “But even back then, she was just that kind of girl. When I said I didn’t have any clothes, she said, ‘You can wear mine.’ When I said I didn’t have any underwear, she said, ‘You can borrow mine, it’s pretty!’ “And the rest, as they say, is history.

Be your BFF’s biggest cheerleader…

When Winfrey was in the midst of a career change early in their friendship, everyone around her seemed to be against the move, except for King. “Gail was the only one who said, ‘I think you can do it!'”

…unless you have to be brutally honest about her style.

Because true friends won’t let their best friend look not so nice on TV. King once appeared on the CBS Morning Show wearing an emerald top and a flashy, oversized bib-style necklace, a style Winfrey was not too fond of. Apparently, the media mogul sent a memo to Dr. King’s assistant that morning: “Tell Gail that she’s on a treadmill and has a circus around her neck and is having a hard time concentrating.”

What was the king’s reaction? “I think she’s wrong.” (Oprah also sent a note about Gail’s lipstick choices, but at least she’s watching!)

You can’t put a price on true friendship

“When she was making $50 an hour, I was making $27 an hour. Someone said, ‘Have you ever felt like you’ve fallen short?'” Dr. King said as a guest on Winfrey’s talk show. “And I said, ‘No, it’s not a friendship based on money.’ I never feel like I’m competing. I never feel like I’m less than.”

Your soulmate should love your BFF too

Stedman Graham, Winfrey’s longtime boyfriend, said in an interview: “Gail is someone I care about, she’s family…I care about them very much and respect them both very much and I’m glad that they’re great friends.” “I love it. I think it’s great. I hope[they]can be friends forever.” (Looking for your own Steadman? Check out Oprah and Gail’s series of relationship advice videos.)

It’s normal to argue over trivial things.

“I don’t really like birthdays, and neither does she,” Winfrey told the studio audience about King. “Some of our biggest fights have been over birthdays.” (If you know it’s a pain, set the rules in advance: Oprah and Gail no longer exchange Christmas presents because they “really don’t want any.”)

However, the two never had a serious argument, Winfrey confessed to PEOPLE in 2021.

express your feelings openly

Despite being inseparable, Winfrey emotionally revealed in a 2010 interview with Barbara Walters that she had trouble expressing to King how much she appreciated their longtime friendship.

“She’s…the mother I never had. She’s…the little sister everyone wants. She’s the friend everyone deserves. I don’t know anyone better. I don’t know anyone better,” Winfrey said through tears. “I…I’m tearing up because I think about how much…I probably never said that to her.”

Remember: if she knows all your secrets, someone might slip up!

Have you ever wondered what Oprah does when she wants to be free? Let Gail tell you all about it. “Oprah has smoked a little bit of marijuana too, okay to say. I’m not talking outside of school,” she told Ellen DeGeneres. Gail, can you elaborate? “I refuse to answer because she could be found guilty!”

Prioritize each other’s experiences

You learn a lot about a person while traveling. For Winfrey and King, that adage rang true during their 3,600-mile, two-day road trip. It was all recorded on Winfrey’s popular talk show.

“When you’re on the road for a long time, you just get stupid for no reason,” King said of their time together, over a montage of his famous friends goofing around in a store.

Let’s be there for each other in difficult times

Winfrey and King spent New Year’s Eve at Kula Hospital on Maui after King sprained his ankle during a trip to Hawaii in 2014. To make sure the BFFs had a memorable time, Winfrey flew the King family to the resort, where they all celebrated the new year together.

find an excuse to spend time together

What’s better than a tropical vacation with your BFF? Get paid to go on a tropical vacation with your BFF! Oprah and Gail went on a three-day “girls trip” to New Statendam, Holland America with 2,600 of their closest friends in January 2019, the day after Oprah turned 65.

Show up — literally.

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

“My ex-boyfriend was planning on having a baby,” said Gail, who at the time was an anchor at WFSB in Hartford, Connecticut. “I was on the phone with Oprah that morning, and I said, ‘What are you guys doing?’ And she said something to me.”

King, who was preparing to spend the night alone, was “shocked four hours later when the doorbell rang and she and Stedman (Graham) were at the front door,” she said. “She was coming. I didn’t know that… I just kept saying, ‘I can’t believe you guys are here.’ It was something I’ll never, ever, ever forget.”

Introverts and extroverts complement each other well

Although similar in many ways, from their values ​​to their interests, Winfrey and King’s ideal evening is very different. Speaking to PEOPLE in the 2021 Beautiful issue, the Good Morning America anchor said she “loves a good night out,” while Winfrey prefers curling up at home with a book.

The friendship is out of this world

In 2025, when Martin Luther King Jr. joined an all-female crew that blasted off to the edge of space on a Blue Origin rocket, Winfrey appeared overcome with emotion as she watched her friend’s momentous moment from the ground.

“It’s more than just this moment of going up into space. I think this is going to be an everlasting experience,” Winfrey said on the Blue Origin livestream. “Gail has supported me at hundreds of events. I can’t even remember them. But none of us will ever forget this day.”