How Diana Ross’ sparkling diamond earrings became one of Oprah Winfrey’s earliest aspirations
TheGrio...
The media mogul reflected on how Sidney Poitier, Diana Ross and Maya Angelou helped her see herself—and her future—in popular culture.
Oprah Winfrey says one of her earliest symbols of success wasn’t a television studio or a magazine empire—it was a pair of diamond earrings inspired by Diana Ross.
Reflecting on the first moments she felt represented in media for Glamour Magazine’s “Girlhood Firsts” series, the media mogul shared that watching Ross perform during her iconic 1983 “Concert in the Park” in New York became a defining memory. As rain poured over the stage, Winfrey recalled being captivated by one detail: Ross’ sparkling diamond earrings.
“I remember calling her production company the next day,” Winfrey said with a laugh. “I asked them, ‘What was the mascara? And how many carats were the diamonds?’”
She was told the earrings were 10 carats, a revelation that became a personal goal.
“So I strived until I could get my first 10 carats,” she said. “Then later, she told me it was only five. So I could have quit halfway through.”
While the story draws laughs, Winfrey said it reflected something much deeper: what it meant to finally see glamorous, accomplished Black women on television.
Watching Ross and The Supremes perform on “The Ed Sullivan Show” left an indelible impression.
“We had never seen Black women look like that,” Winfrey recalled. “We had not seen Black women be that glamorous. We had not seen Black women talk like that.”
Ross wasn’t the only figure who expanded Winfrey’s sense of what was possible.
She also recalled lying on the floor of her childhood home at age 10 watching Sidney Poitier become the first Black man to win the Academy Award for Best Actor. Seeing him arrive among Hollywood’s biggest stars planted a seed.
“I remember thinking, ‘If he could do that, I wonder what I could do,’” she said.
Winfrey also credited Maya Angelou and her memoir, “I Know Why the Caged Bird Sings,” with helping her feel seen for the first time. The book’s portrayal of a young Black girl growing up in the South mirrored parts of Winfrey’s own childhood, including surviving sexual abuse and finding refuge in reading.
Taken together, Winfrey said those moments of representation did more than inspire admiration—they expanded her imagination, proving that Black excellence, beauty and resilience belonged at the center of the story.