Naomi and Wynonna Judd appear on Oprah's country music show in 1990.

July 30, 1990
They made their Oprah Show debut in a country music showcase and stole the show. "I have the solution for all the other mother-daughters out there who aren't getting along," Wynonna jokes. "I figure if you put them on a bus, let them travel up and down life's highways for about six years, they'll either kill each other or they'll make it. And I'm figuring on winning the Nobel Peace Prize any day now."

Naomi was also asked about her youngest daughter, Ashley. "She should be arriving in Hollyweird, California, today to be an actress," she said. "Bless her heart, she can't carry a tune in a bucket."

Though she performed twice during the show, Naomi later admitted her then-recent hepatitis C diagnosis had zapped some of her energy. "I barely remember doing that show, actually," she said. "That's when I was still hiding it."

Naomi Judd thanks Don Potter on Thank You Day

September 19, 1994
When Naomi learned Oprah was hosting a national "Thank You Day," she instantly knew who she wanted to honor—Don Potter, the Nashville producer credited with creating the Judds' signature sound.

Speechless, Don listened as Naomi shared one of her favorite memories. "We'd never been in a studio. We're sitting there just scared out of our brains—a couple of hillbilly girls in a lot of trouble, actually—and he started us out with a prayer," she said. "[He] got all the musicians around us and he said, I'll never forget it as long as I live, he said, 'Father, we ask that this be pleasing to your ears and that you use this music to heal these two girls and that this music go out into the world to help touch and heal other lives.' And from then on, our lives changed."

Ashley, Wynonna and Naomi Judd's first television interview together

May 15, 1995
By 1995, the Judd women had gone through many transformations. A hepatitis C diagnosis put Naomi's performing career on hold, but it didn't stop her from becoming a best-selling author and executive producer. Wynonna became a new mom and triple-platinum solo artist. Ashley had established herself as one of Hollywood's most promising young actresses.

In their first television interview together, Naomi, Wynonna and Ashley proved they weren't only a show business dynasty—they were a family with struggles like any other. "The Judds are normal people," Naomi said. "We're unpredictable because real life is unpredictable."

Watch as Naomi, Wynonna and Ashley discuss their relationship Watch  

Ashley, Wynonna and Naomi Judd's revealing after the show conversation

July 11, 1995
After their first interview together ended, Naomi, Wynonna and Ashley stayed to thank the audience—and wound up taping another show!

As the Judds took questions from fans, the conversation eventually turned to Wynonna's weight—and lead to one of her most triumphant Oprah Show moments ever.

Watch the moment that had Oprah high-fiving Wynonna! Watch
Wynonna Judd on location

September 9, 1997
As a lead-in to the Season 12 premiere, a select group of guests shared their must-see clips during "Celebrities' Favorite Oprah Show Moments Week." While on location at the Puyallup Fair in Washington, Wynonna talked about her favorite moment. "My fondest memory of being with you was back in 1995 when the three Judd women got together for the very first time on a talk show," she said.
Naomi Judd discusses her hepatitis C remission.

March 5, 1998
When diagnosed with hepatitis C in 1990, Naomi said doctors only gave her three years to live. In 1998, Naomi flew to Amarillo, Texas—where Oprah was taping her show—to announce she was in remission.

Naomi, a certified nurse, said she used a combination of conventional and complementary medicine to treat her mind, body and spirit. "Never ever, ever give up hope. Cling to hope because it's going to help you cope," she said. "Use my story as an example. Let me give you hope. "
Ashley Judd in Suriname

Photo Credit: Getty Images

February 16, 2000
The humanitarian side of Ashley Judd shined brightly during a show about celebrity adventures. Ashley traveled more than 3,000 miles on three separate planes to reach the South American country Suriname, where she wasted no time learning the local way of life.

Ashley also took a canoe to a remote village of 100 people that had no indoor plumbing, garbage floating in the river used for bathing and mosquitoes the size of her hand! Still, she said her weeklong adventure taught her a lot about the spirit of life.
Ashley Judd and Natalie Portman

April 27, 2000
Between world adventures, Ashley stopped by The Oprah Show with actress Natalie Portman to discuss their movie Where the Heart Is, based on the Oprah's Book Club selection by Billie Letts.

During the interview, Natalie revealed Ashley is "the queen of games." Ashley taught Oprah how to play her favorite, Druthers, and asked a question no one could have seen coming: "Would you rather have a third big boob or a big third buttock?"

Watch to see Oprah's answer Watch  
Naomi Judd on aging gracefully

May 2, 2001
Naomi invited cameras into her Tennessee home to talk about aging. "I'm 55," she said. "I'm the speed limit, but I am not slowing down."

Aside from healthy eating and plenty of sleep, Naomi said peace was the key to feeling and looking radiant. "Happiness is the best cosmetic—it gives you less lines, less wrinkles," she said. "I'm not growing older; I'm just growing."
Ashley Judd, Sandra Bullock and Ellen Burstyn

May 29, 2002
Ashley literally kicked off her shoes for some good old-fashioned fun with her Divine Secrets of the Ya-Ya Sisterhood co-stars Sandra Bullock and Ellen Burstyn. She also celebrated a major personal milestone —her marriage to race car driver Dario Franchitti.

Ashley said the experience taught her not to live in fear of the paparazzi. "About three or four weeks out, a bunch of things were in the newspapers and they were all totally correct, and I had this, like, Victorian reaction where I got a fever. My disposition became incredibly tender and faint," she said. "And I thought: 'This is the greatest event of my life, and it's got to be like everything else. I've got to really put my philosophy to the test: Water off a duck and what really matters. You've got to let it go.'"
Wynonna Judd talks about her weight in Oprah's office.

February 11, 2004
When Wynonna's weight hit an all-time high, she asked Oprah for help. With her husband, Oprah's trainer Bob Greene and producers in the room, Wynonna told Oprah why she felt her life was spiraling out of control. "I'm in trouble because I lost myself. I'm the woman who forgot to put herself on the list," she said. "I'm losing my way here." Just two weeks after that conversation, Wynonna was arrested for drunken driving.

Read more about Wynonna's struggle with weight and the family secret she didn't learn until age 30. 

With Bob's help, Wynonna committed to improving her health and getting her life back on track.

Wynonna, Ashley and Naomi Judd

May 10, 2004
Three months later, Wynonna returned to The Oprah Show to share her weight loss progress—and have a serious conversation with her family. Wynonna says her family had never discussed her weight with her and invited Ashley and Naomi on the show to talk about it for the very first time.

Watch Ashley and Naomi reveal why the family never addressed Wynonna's weight Watch  
Wynonna, Ashley and Naomi Judd

August 27, 2004
The cameras kept rolling after Wynonna, Ashley and Naomi's frank conversation, and their after-the-show discussion aired later that summer. Though finally admitting her issues to her mother and sister was tough, Wynonna said she was relieved to have everything on the table. "There's all this emotional stuff in this entanglement, and I feel myself little by little sort of setting myself free, and I think I'm celebrating that today," Wynonna said.

Ashley also offered words of support for her sister. "For what it's worth, I think you're doing great. I want you to be happy, I want you to be healthy and I think this is an incredible odyssey and you are excavating in a way that you've never had to," she said. "I've always recommended to you to keep those elbows out fairly sharply because boundaries are good and you've sometimes resented that mine are so strong. Well, I will give them to you, willingly."

Wynonna Judd

November 8, 2004
After finally discussing her weight with her mother and sister, Wynonna found there were many obstacles on her way to recovery and gained back the weight.

Find out why Wynonna became depressed

Seeing her own despair, Wynonna decided to take a drastic step. She told Naomi she needed space and shared how she delivered the painful news to her mother. "I had to write her a letter and say: 'I need some time. I want to figure out a way to disentangle without severing our ties. It feels like a death ... It's sort of like the death has to happen for the rebirth. I have to do some work right now and find out what it is I want from this relationship, because I want it to be different.'"

Still, Wynonna hoped to find the strength to change her life. "You fall down and you get back up. And I'm in the 'getting back up' stages," she said.
Wynonna Judd

September 27, 2005
Nearly two years after breakdown in Oprah's office, Wynonna emerged feeling more empowered than ever. She had come to terms with three difficult areas in her life: food, family and finances. "I woke up this morning and I thought, 'What's my motto for today?'" she said. "And it was, 'I may not be where I want to be, but I'm sure as heck not where I was.'"

See how she changed her life at home

After not speaking to her mother for six months, Wynonna reported their relationship was much better. "I'm learning to ask for what I need because we expect family members, mates, to really read our minds."
Vince Gill, BeBe Winans, CeCe Winans and Wynonna Judd

November 5, 2008
The morning after Barack Obama was elected president, Wynonna joined Vince Gill, BeBe Winans and CeCe Winans to sing a special song, "We Need One Another Right Now," on Oprah's stage.

Watch the performance Watch
Wynonna Judd at Fort Bragg

November 24, 2009
Just in time for the holidays, Fort Bragg welcomed home 3,500 soldiers from a deployment in Iraq. Wynonna wanted to be there personally to say thank you. "The thing that really humbles me about the military is the humility with which these people operate," she said. "It's about community—common unity. There's no one person. It's a team thing."
Wynonna Judd, Naomi Judd and Oprah

September 14, 2010
Twenty years after their first Oprah Show appearance, the Judds are back!

See what they had to say about Wynonna's devastating divorce and reviving their mother-daughter relationship.