Oprah Winfrey Hilariously Recalls a Joke Gayle King Once Made About Her Cleavage

October 11, 2024

Oprah Winfrey and Gayle King have been best friends for more than 40 years!

In a new episode of The OG Chronicles for O, The Oprah Magazine, Winfrey and King offer riders aboard their Holland America cruise advice about friendship and much more. The long-time best friends' words of wisdom lead to some hilarious stories from the pair, one of which has to do with Winfrey's cleavage.

"I think there's a way you can tease a friend without it feeling like you're tearing her down or taking a dig," 64-year-old King says, before recounting a story about one time when "Oprah had on a dress with a lot of cleavage."

Apparently, the CBS This Morning co-host called up Winfrey, 65, and revealed that she had a black eye.

"I said, 'Oh my god. What happened?'" Winfrey recalls. "You said, 'I passed the TV and your boob hit me in the eye.'"

Another playful disagreement came when King got blonde highlights and Winfrey made sure to make her feelings about them very clear.

"I got some blonde highlights in my hair that everyone said looked good and Oprah said, 'You look ridiculous! Why do you think blonde looks good?'" King says. "I go, 'This isn't blonde, this is highlights in my hair.'"

"She's telling me, 'This is what the sun did to my hair.' OK. OK," Winfrey explains with a laugh.

"I wasn't even offended by that," King says. "I just disagreed with her."

When one cruise passenger asks about making new friends, King laments that "it's hard" to do so.

"I think you may be scarred because remember you had that friend who slept with your husband?" Winfrey says. "And when you found them with your husband you said, 'I thought you were my friend!'"

"She said, 'I never liked you,'" King reveals while laughing.

The pair, who have been BFFs since they were in their early 20s, think their relationship works because they've always respected and never envied each other.

"The reason why our friendship is so great is because... I've always wanted the best for her and she's always wanted the best for me," Winfrey says. "... Gayle is the kind of friend who's secure enough in the friendship, I'm the kind of friend who's secure enough in the friendship, that if she wanted to bring another friend in neither of us thinks, 'Oh, that means I have to move out.'"

"You cannot maintain a relationship with people who lose oxygen as you're on the climb of your life," Winfrey adds later in the video. "And, along the climb, lots of people lose oxygen as you reach higher altitudes... They can't handle the altitude. Then you have to let them go."

ET's Nischelle Turner was on board the cruise and caught up with both Winfrey and King who gushed about their friendship.

"Everybody should have a Gayle," Winfrey said, "And I love that people have come [on the cruise] and they introduced people, and they say, 'This is my Gayle.'"

Watch the video below for more on the pair:

Video

Oprah Winfrey and Gayle King Talk Years-Long Friendship and Setting Each Other Up (Exclusive)

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