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Oprah Looks Back on the Most Embarrassing Moment of Her Entire Career

The talk show host's most mortifying experience happened in front of thousands of people.

We all have our most embarrassing moments: Those humbling experiences that we just can't let ourselves forget. Even those stars who never seem to set a foot out of place get mortified once in a while. Take Oprah Winfrey, whose most embarrassing moment happened—literally—on a world stage. In typical fashion for the relatable host and businesswoman, Winfrey was game to relive it, in detail, when an audience member asked. Read on to find out where and when this humiliation occurred, and for more truth-telling from Winfrey, check out Oprah Says This Was the Worst Guest She Ever Had.

Read the original article on Best Life.

Oprah Winfrey's most mortifying moment happened in the '90s.

Oprah Winfrey After the Show

During a 2017 After the Show Q&A, Winfrey literally jumped at the chance to share this embarrassing moment with her studio audience. It happened when she emceed the opening ceremony of the 1994 World Cup, which took place in Chicago.

Always a professional, the host saw the potential for disaster when she was preparing for the event. She even warned the crew.

"I'd rehearsed the day before, and I said to them, 'You guys have this plastic covering the stage that is the same color as the stage, so you guys really need to change that,'" Winfrey recalled. "They did not."

And that's where Diana Ross comes in.

Diana Ross
Featureflash Photo Agency/Shutterstock

Diana Ross was one of the stars performing at the event; naturally, it was Winfrey's job to introduce her to the entire audience at Soldier Field.

The singer made her entrance from the field, walking towards the stage. That's when Winfrey was supposed to make her exit.

"I turn to walk off the stage and fell in a hole," the host recounted. "The hole that was covered with the plastic. I went straight through the plastic. I went down in this big pit in the hole, fell, scarred up my legs, was bleeding. I couldn't get out, but I could still hear Diana singing."

For more cringeworthy moments, check out The Embarrassing "Friends" Gaffe You Never Noticed Before.

And the rescue was just as humiliating.

Oprah Winfrey falls at the World Cup Opening Ceremony in 1994
Peter Robinson – PA Images via Getty Images

Winfrey went on to say that she could hear event security repeating, "Get her out, get her out of the hole!" Four guards came to rescue her, carrying her "spread eagle" out of the pit.

"I'm bleeding, I go to the other side, they bandage my legs, and I limp back up, and I say, 'That was Diana Ross!'" Winfrey continued.

And she wasn't the only one who tripped during the event. One of her other duties was to announce the Parade of Nations, which led to the hole claiming more victims. Another performer, Jon Secada, "could not get himself out of the hole, 'cause there was no time," Winfrey said. "So he sang from the neck up!"

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But Winfrey carried on with the show.

Oprah Winfrey and Diana Ross at the 1994 World Cup
Nandy Ross/YouTube

Winfrey said she was lucky that the camera wasn't on her when she fell, so she was able to save some face. You can't see the incident in the YouTube clip of the ceremony, but, as a commenter points out, you can see that her dress is torn when she joins Ross on stage after her performance.

Of course, the star took it all in stride. "I'd always said this, okay, you can't have an embarrassing moment because anything that happened to you has already happened to somebody else," Winfrey told her audience. "But I don't know anybody who fell in the hole at the world soccer cup thing in front of thousands of people and had to be carried out spread eagle."

And for more revelations from beloved talk show hosts, check out The One Guest Ellen DeGeneres Banned From Her Show.

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