‘I’m Done with It’: Oprah Winfrey Condemns Keenen Ivory Wayans, Other Comedians for ‘Hurtful’ Skits About Her Weight Over the Years

Oprah Winfrey never saw the humor in her struggles with weight being mocked for public consumption.

Years of yo-yo dieting and testing out new fads promising to melt the fat away came to an end this year when the media mogul debuted her slim figure while promoting the reimagined “Color Purple” ahead of awards season.

She would later reveal that her shocking transformation was aided by a weight loss drug, though she steered clear from disclosing if she had opted to take the widely popular Ozempic. In a new interview for “The Jamie Kern Lima Show” podcast, the 70-year-old reflected on what it was like for the world to witness her fluctuating weight.

In particular, she referenced the infamous 1988 episode of her eponymous daytime talk show when he lugged a physical representation of the 60-plus pounds of fat she had lost onto the stage. She revealed to podcast host Lima that the nearly 70-pound weight loss was the result of her not eating “a morsel of food for five solid months in losing that weight on Optifast.”

Oprah Winfrey (left) says Kim Wayans’ 1988 “In Living Color” skit of her eating until she bursts (right) was the “most hurtful” ridicule the former talk show host faced during that era. (Photos: @oprah/Instagram, In Living Color)
Oprah Winfrey (left) says Kim Wayans’ 1988 “In Living Color” skit of her eating until she bursts (right) was the “most hurtful” ridicule the former talk show host faced during that era. (Photos: @oprah/Instagram, In Living Color)

Oprah said, “Three days later, I was five pounds heavier, and a week later, I was 10 pounds heavier, and that show happened in November.” By December, she gained more weight and felt ashamed that she had been unable to sustain her slim figure. She chose not to attend a party hosted by Don Johnson of “Miami Vice.”

“I wouldn’t go because I thought I was too fat to go. I had gone from 145 on the day of the show to … I think I was 157 in the course of like a week and a half or two, and the shame started again.”

She got emotional as she shared the shame she felt after being named at the bottom of fashion critic Mr. Blackwell’s list of the best and worst dressed. She said it was 1987, and she was on the cover of a magazine with the headline “Dummy, Frumpy and Down Right Lumpy,” wearing a black dress she had custom-made.

“I took in all the shame,” Oprah explained. “Making fun of my weight was a national sport for 25 years. Comedians did it. The best comedians did it. The highest comedians did it. People with their shows did it. It was just accepted that you can make fun of me.”

She said the humiliation worsened when the sketch comedy show “In Living Color” began to make fun of her fluctuating figure. It was “one of the most hurtful things,” she said. The show was created by Keenen Ivory Wayans and starred his siblings Damon, Kim, Shawn, and Marlon, and a host of other acts who would go on to become household names.

Kim Wayans regularly portrayed the journalist as a woman who was unable to control her eating habits and the ways in which she thought about foot. One skit in particular especially left Winfrey feeling tormented.

“‘In Living Color’ had done a skit where the woman was doing something, and she just kept eating and getting fatter and fatter and fatter, and the comedy bit was that eventually she just exploded,” the billionaire mogul recalled.

The bit appeared in season 1, episode 4. Kim played Winfrey as she gorged various foods, steadily inflating and exclaiming, “Food is my lover! Food is my friend!” until she burst. “The whole audience fell out [laughing], and the woman was me.”

“@Oprah about to go slap all the wayans brothers and sister for in living color,” an X user said, referring back to one of the episodes.

However hurtful the jokes may have been, they did not stop Oprah from welcoming the comedy family onto “The Oprah Winfrey Show” in 2004. The Academy Award-nominated actress sat down with the five siblings again in 2013 for “Oprah Prime” on OWN about their lasting impact on entertainment.

The producer said in 2021 that she began to lose weight after undergoing knee replacement surgery on both legs. She frequently posted videos of her miles-long treks among the hills in Hawaii with her longtime friend Gayle King.

Though many were pleased with Oprah sharing her more vulnerable side after enduring decades of criticism. One YouTube comment read, “Some of the same emotion rose up in me as when I read Worthy. I cried as Oprah shared for all that she has carried in the public eye. And I cried for all the shame I have privately carried as I turn 70 in August. Thank you both.”

Another wrote, “What the doctors need to talk about is the Standard American Diet! Loaded with sugar and salt, that’s Highly addictive! And it’s like a drug that causes someone to constantly want to eat. In addition to many people having these chronic Diseases. Yes Oprah I’m glad you stop beating yourself up !”

Since coming clean about her use of a weight loss drug, Winfrey has faced backlash and, more recently, ridicule after being treated for gastrointestinal issues. Many speculated that her ailment was a side effect of the undisclosed weight loss drug.

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