Looking Back: 24 Wildest Moments From ‘The Oprah Show’

“You get a car! And you get a car!” Tom Cruise leaped off Oprah's couch, proclaiming his deep love for Katie Holmes. The Teenage Mutant Ninja Turtles referred to a strange interspecies relationship before a group of children. What hasn't happened on The Oprah Winfrey Show?

1. Mary-Kate and Ashley's Size Controversy 

Oprah decided to ask child actors about their struggles with an eating disorder through a series of rude, unprofessional questions on public television. Rumors spread, as they do, about Mary-Kate's alleged eating disorder, so Oprah launched into an off-putting question that switched the interview's tone.

“New rumors have recently surfaced that really upset you, right? Ah, you know, the one about eating,” the host inquired. Ashley jumped to her sister's side, responding respectfully about not reading comments, but Oprah didn't allow that polite answer to sway the interview's course. She continued to ask the twins their size, questioning their answers.

2. Robin Williams and Nathan Lane's Awkward Interview 

Robin Williams and Nathan Lane appeared on Oprah during the The Birdcage promotional tour. Excited to speak about his starring role in the film, Lane beamed as he headed into the Oprah interview. When he sat down and Oprah began firing questions, she targeted his unconfirmed sexuality rather than him achieving his dreams.

Oprah asked Lane if playing a gay character instilled any fear of getting typecast in future roles. Robin Williams, rest his soul, pointed out Oprah's vocal inflections, adding a bit of comic relief and shifting the conversation. 

3. Drew Brees' Birthmark Discussion 

The New Orleans Saints/Los Angeles Chargers quarterback accepted an invitation to Oprah's show in 2010. As the revered football legend sat down, Oprah jumped toward him, asking who kissed him. Most people who know what Drew Brees looks like know of his birthmark. That action highlights Oprah's lack of research.

4. Wagon of Fat Debacle 

What says, “I've lost weight!” like wheeling around a wagon of fat? Donning a sleek black turtleneck tucked into blue jeans, Oprah tugged out a wagon filled with 67 pounds of lard- the amount of weight she lost. At the time, the idea seemed empowering, at least to Oprah, but looking back, it's all a bit fatphobic. 

5. Tom Cruise Jumping on the Couch

Who doesn't remember Tom Cruise jumping onto Oprah's couch after she asked him about his new love affair with Katie Holmes? He punched his hands into the air and jumped off the couch, folding into laughter over his expression.

6. Michael Jackson's Virginity

Michael Jackson met with Oprah for his first interview in 14 years. The singer spoke with the talk show host in a 90-minute segment on rumors, love, and whether or not Jackson participated in adult relations. He gasped when Oprah asked him, “Are you a virgin?” and responded, “How could you ask me that question? I'm a gentleman.”

7. Elizabeth Taylor's Drama 

Beloved actress Elizabeth Taylor conversed with Oprah in 1988. Before the camera crew hit record, Taylor pleaded with Oprah to stay away from her romantic life and stick to her book Elizabeth Takes Off. Oprah disobeyed the request and pried into Taylor's private life, attempting to gnaw away her guard and uncover her current boyfriend. Oprah mused about the situation, joking about Taylor's secretive answers. At one point, Taylor assured Oprah her personal life was none of her business.  

8. The Fake Memoir Scandal 

Author James Frey wrote A Million Little Pieces, a non-fiction (everyone thought) novel about his addiction and recovery process. Oprah applauded his writing, placed his book in her book club, and invited him onto the show to sing praises. A year later, reports alleged Frey falsified events in his book and wrote a piece of fiction with some basis of truth. Oprah invited him back on the show to interrogate him and ask if any parts of the book were classified as non-fiction. He admitted he embellished some bits and could not remember other crucial events he spoke on. 

9. Lance Armstrong's Doping Confession 

Getting Lance Armstrong to admit to ingestion of illicit substances on national television is a feat Oprah tackled with zero effort. The famous athlete won first place in the Tour de France seven times in a row, but not without the help of choice substances. Oprah interviewed Armstrong in 2013 with a long list of straightforward questions centered around Armstrong's performance enhancers. He answered without pause, sharing his truth.

10. Teenage Mutant Ninja Turtles' Relationship Woes 

Judith Hoag (April O'Neil) and the band of four-shelled creatures named after famous artists joined Oprah for one of her show's weirdest, wildest moments. Kids piled into the audience, glistening over their favorite superheroes as Oprah asked a strange question. “Is there one of the turtles you like more than the others? I mean, is there anything romantic or anything?” Oprah probed Hoag.

April turned into her hands, blushing, saying, “There are children here. I can't say that. The more you know the turtles, the more attractive they become.” The camera panned to the in-audience parents glaring at the guests, expecting the moment to end with that odd comment. It didn't. Raphael shouts, “Oprah, I've been trying to talk her into an interspecies relationship for months now.” We don't know how this passed through television ratings. 

11. David Blaine Underwater Stunt 

World-famous magician David Blaine tacked a world record on Oprah's show, trying to hold his breath for 17 minutes. The segment featured an interview the day before the stunt, where David detailed the painful moments near the end of the act. He said the most difficult part of holding his breath entails the last six minutes when his body wants to breathe. Yet, he forces his brain to remain still without oxygen. We all held our breaths, watching this air.

12. Dolly Parton's Plastic Surgery Discussion 

Madame Dolly Parton stuck to her respectful country roots when Oprah shed judgment on her plastic surgery operations. Parton joked of her cartoonish appearance, laughing about always looking the same. Oprah continued to prod, mentioning her honesty about plastic surgery. Parton agreed with her, saying, “Yes, I have, and I'll have some more when I need 'em.”

13. Alien Abduction Interview 

Two women, Dorothy Wallis and Constance Morgan, accepted guest spots on Oprah's show during her first season. The two women explained their scary encounters with alien abduction and knew others would refuse to believe them. Morgan and Wallis shared their stories, revealing that the aliens abducted, watched, and tested them in their spaceships. 

14. Mad Cow Disease Controversy and Lawsuit 

Remember the lawsuit against Oprah? The powerful woman pledged to never consume another hamburger after learning about Mad Cow disease and the effects of contaminated beef on the human body. The beef industry claimed their sales dropped $11 million, resulting in a public outcry against the beef industry. So, they did what any industry Oprah defamed would do. They sued, and Oprah won. 

15. Car Giveaway 

Everyone recalls Oprah's excitement over gifting everyone in the audience a new car. How can one forget the uproarious applause encapsulating the room following Oprah's announcement, “And you get a car! and you get a car!”?

16. Ellen's Coming Out Interview 

Former talk show host Ellen declared her sexuality in 1997. Ellen's sitcom Ellen saw her as a gay character, which caused audiences to wonder about the validity of the actor's sexuality. So, she completed an interview with Time and stepped on Oprah's platform, wearing a simple sweater and dark jeans to clarify her astounding public announcement. She reiterated that existing as a member of the LGBTQ+ community is okay, even though she's fallen out of favor due to allegations of rude or mean behavior toward guests and workers on her show. 

17. Barbra Streisand's Microphone Arts and Crafts 

We can't stop a diva from diva-ing any more than we can stop a talk show host from questioning their interviewee. “I own this studio, I've been here, I don't know how many years, I've never seen a white mic,” Oprah gestured toward the microphone Streisand held opposite her puppy, who also adopted a white coat. Streisand joined in on the joke, dodging the discomfort. “It's actually off-white to match my off-white sweater,” Streisand revealed she spray painted the mic without Oprah's permission, and Oprah cut to commercial.

18. Brown Eyes/ Blue Eyes Experiment 

A teacher and activist, Jane Elliott, introduced her anti-racism experiment to Oprah's audience without their knowledge. She split audience members with blue and brown eyes up, favoring the ones with brown eyes and treating them to donuts and prime seating. Blue-eyed spectators did not eat anything and sat after the brown-eyed guests got situated. Elliott taught the audience how easily humans adapt to racism and segregation.

19. Terry McMillan Interview 

Network television focused on views before we posted on TikTok for likes and Instagram photos for followers. A 2005 episode of The Oprah Winfrey Show featured two guests: Terry McMillan and her gay ex-husband, Jonathan Plummer. Many moments allowed Oprah to approach the topic sensitively, but she ignored each venue and stuck to a humiliating tactic. She kept asking Plummer how he didn't know his sexuality when he married McMillan, and McMillan threw her head around, annoyed with the interview and the situation.

20. Mackenzie Phillips Confession 

A 2009 interview with Mackenzie Phillips and Oprah focused on Phillips's book about her addiction and her relationship with her biological father, John Phillips. Phillips divulged that the relationship turned into a consenting relationship, and Phillips got pregnant but terminated the pregnancy, unaware if she and the baby shared a father. 

21. Sarah Ferguson Royal Family Drama 

Can't we all use a little honesty in our lives? Sarah Ferguson, the Duchess of York and former wife to Prince Andrew chatted with Oprah over the misleading fairy-tale story everyone thinks of the Royal Family. “You didn't marry to get the fairy-tale. You married a man. you fell in love, and you married the man, and then you got to come to terms with the fairy tale.” Ferguson joked that life inside the palace does not equate to a fairy tale but rather real life, at least in the royal's eyes. 

22. Meghan Markle and Prince Harry Interview 

The Duke and Duchess of Sussex, Meghan Markle, and Prince Harry, agreed to an interview with the one and only Oprah a year after their famous departure from Buckingham Palace. The special outlined racial injustices aimed toward Markle about their baby's race and her struggles with depression. She admitted the family always found a way to undercut her issues with depression by bringing up her race.  

23. Forsyth Visit 

Oprah left her studio to venture into the Deep South. A county by the name of Forsyth, a place that claimed no black residents dwelled there since 1912. The segment occurred in 1987. Throughout the segment, Oprah placed a microphone up to Frank Shirley, the self-proclaimed “head of the community of Keep Forsyth and Dawson County white.” The mustached bigot averted Oprah's eyes, stating he's “opposed to communism, race-mixing, and low morals. And homosexuals are of low morals, in my opinion.”

24. Whitney Houston Tell-All Interview 

The legendary Whitney Houston linked with Oprah in a 2009 tell-all. She pronounced issues surrounding her marriage to Bobby Brown and how living in her shadow took a mental toll on his identity. Houston mentioned how she tried to belittle herself to please her man and shrink her success, which led to a drug addiction and substance abuse by his side.