After 18 number-one hits, 67 albums, more than 100 million records sold and half a century in the spotlight, the legendary Diana Ross is more than a music icon. She also symbolizes what can happen when a little girl dares to dream—a little girl like Oprah, who watched the Supremes on The Ed Sullivan Show back in 1964.
"I have to really keep myself from going into the ugly cry," Oprah says about interviewing Diana, "Because of how much this legend, this woman means to me and my life. ... I'm going to try to keep it together."
Before embarking on her solo career in 1970, Diana got her start with Motown as a member of the Supremes, alongside Mary Wilson and Florence Ballard. The Supremes rose to fame with several hit songs, including "Baby Love," "Stop! In the Name of Love" and "Where Did Our Love Go."
In those days, Diana says she had no idea what impact she and the Supremes were making and how they were influencing young girls across the nation. "We didn't really know what to do except to try to be the best we knew how to [be]," she says. "I don't think we felt like we were stars."
"When did you think you'd made it'?" Oprah asks.
"Never!" Diana laughs. "I've never been that overconfident about what's possible. ... When did you think you had made it?"
"I think sitting here with you has made me make it," Oprah jokes.
Diana may not realize her impact, but there's no debate that she's a beloved singer whose concerts pack in thousands of adoring fans—concerts like her infamous performance in New York's Central Park in 1983. During that show, hundreds of thousands of people stood in the pouring rain for hours to see her sing.
"The storm was amazing," Diana recalls. "They tried to get me to get off the stage, and I refused."
Today, Diana says she still loves performing on stage, whether things go perfectly or not, and has had many memorable moments throughout her career, from meeting Nelson Mandela—"That was pretty exciting!" she says—to being nominated for an Oscar® for her portrayal of Billie Holiday in Lady Sings the Blues.
With such an impressive career, it surprises some people to know that Diana has never won a Grammy® Award. (She has been nominated 12 times.) When Oprah asks Diana if this upsets her as much as it upsets her fans, she answers, "No, nothing really upsets me. I just appreciate still having the longevity that I've had in my career."
Diana says she would love to record new songs and currently listens to all different types of music—especially music by her son, Evan."I listen to most everything that's out there because I need to stay aware of what's happening in the industry," she says. "I'm happy to embrace [everything]."
Throughout her career, Diana has had relationships with Motown's Berry Gordy, Robert Silberstein and Norwegian adventurer Arne Naess. Diana's 14-year marriage with Arne ended in 2000, and nearly four years later, he died in a tragic mountain climbing accident. She still calls him "the love of my life."
What did Diana learn from that relationship? "That love is everlasting," Diana says. "And I love him now."
Growing up, Diana's children say that they lived relatively typical lives. "There was a sense of routine and normalcy," says Tracee, her daughter.
They also say that their mother always trusted them and encouraged them to follow their dreams. "Somehow, despite how large her career and her persona [have] been, she has helped us not feel in her shadow," says Rhonda, her oldest daughter. "We can be ourselves. She somehow helped us to have that."
Another one of Diana's roles—besides being a mother, grandmother and singer—is that of an actress. One of her acclaimed movies, Lady Sings the Blues, was nominated for five Academy Awards®. Her other Academy Award-nominated film, Mahogany, featured a theme song sung by Diana, which rose to the top of the Billboard charts.
Despite these successes, Diana says that acting has been a challenging part of her career. "The work of it—the acting part, using your imagination—that was good," she says. "But the waiting and the sitting? I found that, really, I wanted to be with my kids and not sitting in a trailer somewhere."
"But did you love doing those movies?" Oprah asks.
"I loved working with those people," Diana says.
One of the people Diana worked with on both of her most memorable movies was co-star Billy Dee Williams. It has been 35 years since we've seen them together on the big screen and, to Diana's surprise, this legendary actor is here today!
"The chemistry that the two of you had on screen was like something we had never seen before," Oprah says. "Was that real for you?"
"Oh, absolutely," Billy Dee says.
"What do you remember about being on set with Diana Ross?" Oprah asks.
"Her mouth," Billy Dee answers. "How can I explain it? ... It was like putting the perfect puzzle together."
"We worked really, really well together," Diana says.
Diana's done it all. She's had hit movies and chart-topping songs, including Grammy®-nominated "Ain't No Mountain High Enough," the song that gave Diana her first solo number-one single.
With such an amazing career, it's hard to imagine a day when Diana will stop singing, but she says that there's one situation that could get her to stop. "I think that if my voice for some reason changes—because your voice does change—then it's time for me not to sing," she says.