Gayle and Oprah in 1986

Gayle's Big Debut

Oprah Show viewers first met Gayle on a 1986 show about celebrities and their best friends. During the show, which also featured the BFFs of stars from Dynasty and Ryan's Hope, Oprah and Gayle cracked each other up recounting stories about ill-fitting dresses and disastrous hairdos. 
Gayle and Oprah in 1991

Their First Loves

The two best friends couldn't stop giggling in 1991 when they both reunited with their first loves on Oprah's stage! Before their former flames came out to greet them, Oprah and Gayle swapped high school stories and read old love letters.
Oprah and Gayle in 1994

Oprah's 40th Birthday Party

On Oprah's 40th birthday in 1994, she thought she was doing a show about jurors...but instead she walked out to a surprise party! Everyone from Patti LaBelle to Aretha Franklin to Stedman came out to surprise Oprah, but she didn't lose her cool until she saw her best friend Gayle. "This is so touching to me because when Patti was here and then Aretha came and everyone was coming, I thought, 'Gee, I wish Gayle could be here to see this,'" Oprah said.
Gayle and Oprah in 1996

Putting Their Friendship to the Test

What do Oprah and Gayle really think about each other? During a 1996 show featuring a personality test, the best friends were asked to describe each other in just one word. Oprah and Gayle respectively said "nice" and "fun." When asked what people would be most surprised to learn about their best friend, Gayle said that Oprah is really outgoing "but not that social," and Oprah shared that Gayle "can eat enough breakfast for three people."
Oprah and her audience help Gayle find a dress in 1997

The Perfect Dress

In 1997, Oprah and Gayle were both attending the Primetime Emmy Awards—and Oprah didn't want Gayle raiding her closet for something to wear! To keep her best friend at bay, Oprah tasked the audience with the job of picking out Gayle's dress. Gayle looked on via satellite as the audience reviewed five different gowns; a black halter dress by Fred Hayman won out in the end.
Gayle and Stedman play a trivia game in 1997

Gayle Knows Best

It was Gayle versus Stedman during a 1997 show that pitted best friends against boyfriends. The contest took a hilarious turn when Gayle and Stedman were both asked, "What does Oprah enjoy shopping for the most?" Stedman incorrectly answered "panty hose," while best friend Gayle knew the answer was furniture and art.
Gayle and Oprah in 1998

Gayle King, Bargain Hunter

Everyone knows that Gayle is Oprah's best friend, but in 1998, viewers learned that she's also a master bargain shopper. Cameras followed Gayle as she found rock-bottom prices on cleaning products, clothes and even Oprah's Christmas present!
Gayle on a blind date in 2002

Gayle's Blind Dates

Gayle made a bold move in 2002 when she let Oprah Show producers play matchmaker for her, and viewers watched as she went on four blind dates. While Gayle was out trying to find her match, Oprah said she was home "waiting up like a mother." No long-lasting love connections were made on Gayle's dates, but she said she met four nice guys that she wouldn't have otherwise met.


Oprah's 50th Birthday Party

Oprah had no idea what the plan was for her on-air 50th birthday party—but Gayle did! Gayle served as co-host for the big day, which included surprise visits from celebrities like John Travolta, Tina Turner, Stevie Wonder and Jay Leno.
Oprah and Gayle go back in time

Oprah and Gayle Go Back in Time

No phones. No toilets. In 2004, Oprah and Gayle went way back in time (to 1628, to be exact) to live like the colonials did for a PBS series called Colonial House. Their 24-hour Puritan adventure included wood chopping, cooking over an open fire and a good old-fashioned bonfire dance. 
Oprah and Gayle on their road trip

The Road Trip

In 2006, Oprah and Gayle put their friendship to the ultimate test when they road-tripped from California to New York. Along the way, the best friends took in America's sites, played a mean game of bingo and even crashed a couple weddings. 
Girls weekend

A Girls' Getaway

It was the ultimate girls' getaway! For five days in 2006, Oprah and Gayle joined 60 deserving women at the Miraval Life in Balance Resort and Spa in Tucson, Arizona.
Oprah and Gayle learn new dance moves in 2008

Strutting Their Stuff

Gayle loves to dance, but in 2008, Oprah told Gayle she was stuck in a rut. “Ever since I've known her, she's been dancing the same way," Oprah said. "Her moves are stuck in junior high school." Hip-hop choreographer Tweetie came in to show Oprah and Gayle the latest moves—watch what happened!
Oprah and Gayle at the State Fair of Texas

The State Fair of Texas

Oprah and Gayle kicked up their heels in 2009 when they went to the State Fair of Texas. The day's highlights included a competitive game of Flip-the-Chick and a fried-food taste test.
Oprah and Gayle at Yosemite

The Great Outdoors

In 2010, the best friends hit the road once again—this time to Yosemite National Park for an overnight camping trip. After getting a grand tour of some of Yosemite's beautiful sites, Oprah and Gayle set up camp, got to know their neighbors and wrapped up their stay with a mule ride into the sunset.

Look back on all of Oprah and Gayle's ultimate adventures!