A long time ago, Oprah Winfrey was the target of many jokes about her career as a talk show host, her weight, her wardrobe, and her big personality.
The entertainment mogul hosted her show for 25 seasons before it went on-air and morphed into a production company and more.
But the jokes about her time on television have created permanent scars that have yet to go away.
Take, Debra Wilson. The actress and comedian best known for portraying Winfrey on MADtv’s sketch comedy series has a cold message for Winfrey.
The 63-year-old was part of the main cast member for eight seasons before leaving the show. Some of her most well-known skits are about singer Whitney Houston and her erratic behavior.
But the skits about Winfey’s highlighted weight issues generated laughs.
Winfrey, who struggled with weight fluctuation throughout her career, revealed in recent years how it hurt her being the target of comedians’ jokes and being mocked in TV shows like “In Living Color.”
Wilson claimed she caught wind of Winfrey’s dissatisfaction with her impressions. On April 22, Hype+ shared an interview of her admitting how she learned about the talk show host’s feelings towards her jokes.
She started by mentioning that Houston “liked” the skits of her portraying the singer. But Winfrey felt otherwise.
“She thought it was crazy, because she thought that what I did was outrageous. And so it wasn’t an insult to her. I did find out that Oprah was not pleased.”
After chuckling, Wilson mentioned that if she had met Houston in person, she would’ve switched up the skits that she did about Houston’s substance abuse.
She said, “I would probably want to take a different position. I would probably want to play her more diva and less disheveled and ask the writers, can we come up with stuff that makes her more of a diva, you know, like having minions follow her and having her cellphone everywhere and less and less than the drug thing.”
But Wilson doesn’t appear to have the same change of heart for the “Beloved” star.
When asked how Winfrey’s thoughts impacted her, she said, “I didn’t care. Still don’t care.”
She then straightened her posture and turned her voice to sound similar to Winfrey’s and yelled, “You heard me. I don’t care.
Wilson took off her glasses and said, “You’re brilliant. You’re amazing. So what? All I’m saying is you’ve got a school in Africa and you’ve got a network and your best friends Gayle King, and Tyler Perry, and Deepunk Chopra.”
Coming out of her Winfey voice, Wilson added, “Love you girl. Love you. But um seriously, I think you know a lot of people love Oprah for so many things and I don’t really – I think you should not take yourself so serious.”
One of Wilson’s skits shows her portraying a wide-hipped Winfrey walking backstage and eventually grabbing a chicken leg and taking a bite out of it. She eventually noticed herself on the camera, screamed that she had gained 180 pounds over the weekend, and demanded to only be filmed with the “thinning camera.”
When she walks on stage, the camera makes her look slim for television, but in front of the live audience and in real life, she looks heavier.
Wilson said she found out in the early 2000s that Winfrey was no longer a fan of her impressions of her.
Eventually, in 2002, she met Winfrey while on the red carpet with Michael McDonald at the 54th Annual Primetime Emmy Awards. That night, McDonald told Winfrey that Wilson plays her on the show.
Wilson said she “got down on [her] knees’” and sang her praises before her partner, Stedman Graham, grabbed her away.
A clip then shows the moment when Wilson tells “The Color Purple” star, “You look amazing.”
Winfey responded, “Thank you. Working out pays off, working out pays off.”
Winfrey has lost close to 60 pounds since launching her fitness journey and former partnership with Weight Watchers. But some fans will never forget the jokes and decades-long worth of content that came at her expense.
Wilson’s comments were filmed back in 2020. But it’s unclear why the outlet chose to recirculate the conversation that has fans recalling how they laughed at Wilson’s portrayal of Winfrey.
One person who remembered said, “Deb used to GET DOWN on Oprah and Whitney!!” Someone else joked, “This was a whole Oprah impression by default.”
A third said, “We don’t care either. Debra did her thing as Oprah.” More optimistic people have higher Hopes that Winfrey has since moved on. “That was 25 years ago. Oprah may be ok with the impression now,” said a fourth person.
“Now why would you troll that lady in character like that,” said another person, convinced that Wilson was still trolling Winfrey in her response.
“I still think about the Oprah skit to this very day!! “Go out and buy a mountain!!!!””
Though she didn’t directly mention MadTV’s sketches, in 2024 Winfrey opened up on “The Jamie Kern Lima Show” about the hurtful skits comedians did about her weight.
She said, “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.”
The revelation came months after Winfrey debuted her slimmest figure yet in December 2023 during the press tour and red carpet looks for “The Color Purple,” the reimagined version. She later revealed that she had been taking weight loss drugs to help manage her weight.
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