The Most Shocking Moments from The Oprah Winfrey Show

Oprah Winfrey has arguably been the most beloved, popular and controversial talk show host of all time. There were several crazy moments from her show but these are the most shocking. Do you remember these episodes?

1987 – AIDS discussion

In 1987, Oprah made history by bringing a very controversial subject to her show. She spoke candidly to a resident from the tiny town of Williamson, West Virginia (population 5,600). Mike Sisco was a gay man with AIDS. He set off a firestorm of fear and rage by swimming in a public pool.

1987 – AIDS discussion

All of a sudden, this small town was catapulted into the spotlight. This became part of the national discussion about AIDS and the show was riveting. This town hall discussion was one of the most popular shows in Oprah Show history. Williamson residents did not fully understand the disease and this caused widespread fear. People in this small town believed that AIDS could spread through casual contact—like sweat or saliva, from kissing, in swimming pools and even on doorknobs. And they were not alone in their incorrect assumptions. Sisco succumbed to AIDS in 1994.

Next, see what made viewers relate to Oprah.

1988 – Oprah and her Little Red Wagon

Oprah’s ongoing battle with the bulge has kept her human. Many viewers traveled that same battle with her — the battle of the bulge helped her to be a sympathetic character in many viewers’ hearts. Oprah is proof of one thing we can all relate to. All the money in the world can’t buy you a new body. Bottom line: you can’t lose weight if your body won’t cooperate.

1988 – Oprah and her Little Red Wagon

But in 1988, she shocked her millions of viewers by wheeling out 67 pounds of fat! And she walked that fat on to her stage in a little red wagon! It was the exact amount of weight she’d lost by going on Optifast, which was essentially eating nothing for four months. Sure, her bod was pretty lean and mean but sadly, the diet ruined her metabolism and has been going up and down ever since.

Next up, the insane interview from 1989 that was never aired.

1989 – Interview with a Mass Murderer

Oprah has interviewed a wide variety of people, including several killers, so this crazed murderer was hardly unfamiliar company. In her show’s history, Oprah’s been more likely to bring in victims or relatives of the dead to speak about their experiences (like Jim Jones Jr. and John Wayne Gacy’s sister), offering their unique perspectives to her audience. So speaking with an actual mass murderer was a much more shocking idea.

1989 – Interview with a Mass Murderer

It is safe to say that maybe she learned her lesson from this never-aired segment: While interviewing a man who had killed eight people along with some of his victims’ families, she called a halt to the proceeding and ultimately decided this was not the direction she wanted to go.

On the next slide, Oprah interviews 92 people at once.

1990 – Multiple Personalities

In 1990, Oprah interviewed Truddi Chase, a woman with 92 distinct personalities. She was the author of the book When Rabbit Howls, which was an autobiography about her experiences after being diagnosed with dissociative identity disorder. In her autobiography, Chase wrote that she was repeatedly and violently sexually and physically abused by her stepfather. She was also beaten and neglected by her mother during her childhood and teenage years.

1990 – Multiple Personalities

In this emotional interview, Oprah was moved to tears by Truddi Chase. Chase stated that her stepfather denied abusing Chase but in another interview it was discovered that her mother had also sexually abused her. The mother had died just before the book’s publication. Chase died in March 2010 at the age of 75.

Next, the most-watched episode of all time.

1993 – Invitation from the King of Pop

In 1993, Michael Jackson rarely gave interviews— He was reclusive and a bit odd. But then he invited Oprah personally to finally sit down for a candid chat and review any questions she wanted to present to him. At this point in his life and career, he was not yet an accused child molester.

1993 – Invitation from the King of Pop

She visited him at his home at Neverland Ranch. She tackled just about every rumor that had been circulating about him at that time. Some of the most notorious rumors were his gradually whitening skin and whether he owned the bones of John Merrick (aka the “Elephant Man”). The 90-minute show was Oprah’s most-watched of her career, with 100 million people who tuned in.

1996 ­- Mad Cows and the Doctor

This episode was incredibly controversial but not so much for the content but for what happened after the episode aired. First, Oprah didn’t want to know where the beef was— she just wanted to know what was IN the beef. Expert Howard Lyman educated Oprah about mad cow disease and the beef processing industry. After learning about mad cow disease, she stated she’d never eat another burger ever again.

1996 ­- Mad Cows and the Doctor

Texas cattlemen were infuriated. They saw their industry torpedoed by that opinion and sued — and lost—but another interesting result emerged from the trial. Oprah hired Phil McGraw’s company called “Courtroom Sciences” to assist in jury analysis. She liked the owner so much she started having him on her show regularly until he received his own show.

1996 – The Start of her Book Club

Can you imagine a world with no books? Book lovers can’t understand a world where someone has no interest in reading! But Oprah knew there were potential readers out there who loved books as much as she did and just needed to be reached.

1996 – The Start of her Book Club

In 1996, she launched her book club. The first selection was The Deep End of the Ocean and in the process of starting the club, she created superstar best-sellers of her choices. But regardless of the massive publicity and sales from a simple mention on her show, not every author wanted to be chosen for her book club; most didn’t find the show an appealing avenue for publicity. But whatever you may think, Oprah gets millions to read.

2001 – Boy Philosopher, Poet, and Beacon of Peace

Mattie Stepanek was only 11 when he first appeared on her show. This young boy was indeed remarkable; he was a marvel of the human spirit. He was the most inspiring human to cross Oprah Winfrey’s stage. Stepanek, confined to a wheelchair due to his diagnosis of a rare form of muscular dystrophy, had three wishes.

2001 – Boy Philosopher, Poet, and Beacon of Peace

His wishes were to have his poetry published, to meet his hero Jimmy Carter to talk about world peace, and to meet Oprah; All of his wishes came true. Stepanek’s numerous Heartsongs books even reached the top of The New York Times‘ best-seller list. He made such an impact of Carter and Winfrey that after his death in 2004, they both were in attendance at Stepanek’s funeral.

Next, one episode Oprah’s viewers didn’t agree with…

2001 – Islam 101

The year 2001 was arguably the most difficult year in recent U.S. history. And The Oprah Winfrey Show wanted to spotlight one of the most feared and debated topics of that time: Islam. After 9/11, the “Islam 101” episode struck a chord with viewers.

2001 – Islam 101

The dean of Religious Life at the University of Southern California, Varun Soni, discussed Islamic beliefs and common misconceptions. He wanted to inform people about the second largest religion in the world. The most sacred text for Muslims is the Quran, and the prophet Muhammad. Many people felt this episode was in bad taste after the terrorist attack.

2002 – Oprah’s Favorite Things

Who didn’t watch Oprah give away tons of high-ticket, in-demand items around Christmastime each year? Even people who didn’t watch Oprah wanted a golden ticket to her annual giveaway of stuff. These shows were actually never announced in advance. Starting in 2002, Oprah began giving away all sorts of gifts to her audience, which included everything from food items to beauty products to top-of-the-line high tech items.

2002 – Oprah’s Favorite Things

But one fateful year, she gave away big ticket items to an audience of hardworking teachers. And then, it was to volunteers of the Hurricane Katrina cleanup. She skipped 2009 because from what her executive producer said, Oprah “just wasn’t feeling right,” but then went overboard in 2010 — it was two days of “ultimate favorite things.”

See what losing 300 lbs will get you on Oprah in the next slide.

2003 – 300 lbs and a Porsche

At the age of 32, David Caruso weighed in at a whopping 525 pounds. When he realized his life was slipping away, he decided it was finally time to make a change, and he did! He lost over 300 pounds, and had only one wish: He just wanted to sit in a Porsche, the car he had always dreamed of fitting in to.

2003 – 300 lbs and a Porsche

Well, they gave him a Porsche Boxster of his very own! “That still is one of my all-time favorite moments on television,” Oprah said. “The moment that nobody saw was when he was standing in the corner and he just mouthed the words, ‘Thank you’ to me. There’s that moment when you look in a person’s eyes and you see their soul—I was a basket case!”

The unforgettable episode is up next.

2002 – And You Get a Car! And You Get a Car!

And if Oprah’s favorite things wasn’t enough, then there was the car giveaway. The episode started innocently—a Pontiac car seemed to be the topic of discussion. Then Oprah brought 11 audience members to the stage. She shocked them all by telling them they’d each be getting one of the vehicles. Mayhem ensued.

2002 – And You Get a Car! And You Get a Car!

Then, Oprah told the remaining audience members that under everyone’s seat was a gift box, and inside one of those boxes would be a key to a 12th car. But think again! Each box had a key— everyone in the audience got a brand-new car. Pandemonium ensued and even Oprah was losing it, shouting, “Everybody gets a car!” over and over. Of course, the episode was probably much more fun for those in the audience than the folks watching at home but all 276 audience members got a car.

2004 – John Travolta and Oprah’s 50th Birthday

Oprah claims she doesn’t like surprises but she obviously loved this one! When you look back at Oprah’s surprise 50th birthday party—and the celebrity guests that flew in from all over the world to celebrate with her—it is hard to not see the love in Oprah’s eyes.

Oprah's 50th.jpg

One of the long-time producers fromThe Oprah Winfrey Show, helped produce a magical moment with John Travolta. He was there to help Oprah celebrate her 50th birthday but it was all a big surprise. She said, “The day before, John had flown in to practice, and all day long, when it came to the toast, he wouldn’t do it for us. So we were dying to know what the toast was going to be! I thought that he did such a great job. We were crying in the control room!”

Next, Oprah talks about what no one else would on TV.

2005 – Bra Brigade

Millions of women have the joy of wrestling with finding and fitting a bra that they can wear every day but most women are actually wearing an incorrect bra size. Many women have discomfort when wearing a bra, but don’t do anything to find the correct size. Isn’t that when Oprah steps in?

2005 – Bra Brigade

Of course it is! Oprah is here to save the boobs from pinching, hanging and back pain-inducing bras! She invited bra experts help audience members find their correct size. This show was so shocking at the time because women’s breasts and their corresponding bras were generally not an open topic for discussion.

Katie Holmes wishes she could forget about the next episode…

2005 – The Jump on the Couch

By 2005, Tom Cruise’s sexuality had been under scrutiny in the press for years. But when he met Katie Holmes, Cruise apparently couldn’t contain himself and had to give the press something to write about. He decided to go on Oprah for a chat, and her mere query about his new love drove him to act erratically.

2005 – The Jump on the Couch

He began gesturing and kneeling, then got up and jumped up and down on the couch. It was odd in a planned-display-of-overenthusiastic-joy kind of way. Cruise, who has received recognition for his film performances, never got an award for it, but in many ways it was Cruise’s most memorable performance.

2006 – James Frey Debacle

Back to the book club—Oprah placed James Frey’s A Million Little Pieces “memoir” on her book-club list, and many people bought it. Oprah was completely thrilled to feature Frey on her show when she brought him on in October 2005. He was featured in an oddly titled segment called “The Man Who Kept Oprah Awake at Night.”

2006 – James Frey Debacle

But it all came crashing down when it was revealed that Frey had to have made up multiple segments of the book. Frey confessed to the lies, and then even more strangely, went back on Oprah’s show not even a year after his first appearance. She berated him for lying to the public. He later apologized and he even appeared on her final show.

Up next, Oprah hits the road!

2006 – The Best Friend Road Trip

Who wouldn’t want to go on a cross-country road trip with their very best friend? It would be full of laughs, crazy adventures and amazing memories. Obviously, this is why Oprah and her BFF Gayle decided to take a road trip and have it filmed. And many, many viewers tuned in to see Oprah and her best friend behind the wheel.

2006 – The Best Friend Road Trip

Over five episodes, Oprah and Gayle drive cross-country and visit many popular landmarks. They talk story, have some great adventures, meet some very interesting people and have some hilarious, pee-your-pants kinds of laughs that only best friends can have—and her loyal viewers loved every minute of it.

In the next slide Oprah humanizes someone no one else could.

2009 – The Round Table of Batterers

When Oprah held a round table discussion with former batterers, things got very real, very fast. Oprah asked what it takes to change that abusive behavior. The answer from a man named Zeke was quite revealing, it took the producers by surprise.He said “That’s probably the easiest question so far. Learning to tolerate pain, and learning to manage emotions that don’t feel good.”

2009 – The Round Table of Batterers

Zeke’s observation showed everyone that abuse can be a response to pain—and it is socially unacceptable and therefore often misunderstood. “This was a way for us to see it in a new light and maybe reach out to batterers in that way and show them in a different light,” said an executive producer. “I remember when we left. We were both like, ‘Wow. We never thought of it that way.'”

2010 – Final “Favorite Things”

The end of 2010 marked the Oprah Winfrey Show’s final “Favorite Things” show. And it just proves that even Oprah can top herself. People were willing to do anything to get on Oprah Winfrey’s “favorite things” show and they couldn’t imagine what she would do for her final “favorite things”.

2010 – Final “Favorite Things”

Well, it turned into a two-part extravaganza! The audience received gifts ranging from a Josh Groban CD to a 2012 VW Beetle. And once it was over, it was over. The audience was elated to be a part of it, but it was also a bittersweet ending to such an incredible show and giveaway series.

Next, Oprah’s secret relative.

2011 – Oprah’s Half Sister

In 2011, Oprah had a secret. She had been corresponding with a woman for some time who claimed to be related to Oprah. Now, you may be thinking that sure, anyone could claim to be related to a celebrity to try to get tabloid money or short-term fame for a fake story but this one was different.

2011 – Oprah’s Half Sister

This woman knew details and had specific information that sparked Oprah’s interest. And to top it off, she never considered running to the tabloid to exploit this story for money. In 2011, Oprah introduced her half-sister Patricia that she just met to her audience and the world.