Oprah Winfrey’s Best Talk Show Moments

Oprah Winfrey is a household name for many reasons. Despite an incredibly difficult childhood in rural Mississippi, Winfrey went on to triumph in adulthood thanks to a few great teachers and a whole lot of courage.

Winfrey is perhaps most famous for her 25-season talk show, The Oprah WinfreyShow, which inspired its viewers for decades. On top of her role as a talk show host, Winfrey is also an actress, media executive, philanthropist and so much more.

Considered one of the most influential people in the world, Winfrey’s words and actions have given millions of people the tools to change their lives for the better. If there’s any doubt as to the scope of her influence, Winfrey’s “book club” stamp of approval can turn a book into an instant bestseller, and many a retailer itches to be part of Winfrey’s yearly “favorite things” list.

Let’s take a look back at some of her best talk show moments:

Oprah’s wagon of fat

After impressively losing 67 pounds thanks to a liquid diet of Optifast, Winfrey brought the epicness of her weight loss to life by wheeling out a wagon loaded with exactly that much fat.

“At the time I felt it was important to show it that way because I had starved,” she said. “I had literally starved for four and a half months.” Of course, her diet wasn’t exactly successful long-term — once she returned to eating solid foods, Winfrey’s weight crept back up. (Aired November 15, 1988)

Oprah surprised by her fourth-grade teacher

Winfrey credits many of her childhood teachers for changing her life for the better, particularly her fourth-grade teacher, Mary Duncan. In 1989, Winfrey’s producers surprised her by bringing Mrs. Duncan on the show. Winfrey hadn’t seen her since she was a kid, and their reunion was an emotional one.

“I always, because of you, felt I could take on the world. You did exactly what teachers are supposed to do, they create a spark for learning that lives with you from then on,” Winfrey told Duncan. “It’s why I have a talk show today.” (Aired February 1, 1989)

Tom Cruise’s couch jump

When actor Tom Cruise was invited to The Oprah Winfrey Show, it at first seemed like it would be a typical meeting of two celebrities. Instead, when Winfrey asked him about his relationship with actress Katie Holmes, Cruise got up and jumped on the couch. “I’m gone. I don’t care,” Cruise laughed after his epic display of enthusiasm.

“I did not think it would turn into the brouhaha that it did,” Winfrey said of the aftermath. “He was in love. He was very happy about it.” (Aired May 24, 2005)

Oprah’s favorite things

Starting in the 1990s, Winfrey started sharing her “favorite things” every Thanksgiving week. In other words: Products that Winfrey believed would make excellent holiday gifts.

Never one to let down her audience, Winfrey gifted some of the items to the lucky members. The most expensive thing she ever gave away? A brand-new 2012 Volkswagen Beetle. (Multiple episodes)

Oprah’s car giveaway

But let’s be honest, nothing will ever top Winfrey’s now-famous phrase “You get a car!” In 2004, Winfrey stunned her lucky audience members by giving all 276 of them a free Pontiac G6.

To make things even better, audience members had been hand-selected —they were all in desperate need of a car. Winfrey had EMTs standing by in case anyone’s heart started beating too fast from joy. (Aired September 13, 2004)

Oprah’s bra boutique

Sick and tired of knowing so many women were wearing ill-fitting bras, Winfrey demanded that women start wearing bras that actually fit them with her “bra intervention.”

She opened “Oprah’s Bra Boutique” and brought bra experts on to her show to help audience members find the right size. “Women of America, you need to rise up and get a proper bra fitting,” she declared. (Aired May 20, 2005)

Oprah and Gayle’s road trip

In 2006, Winfrey and her best friend, Gayle King, decided to take on the United States in a big way by taking a 3,000-mile road trip across the states in a red Chevy Impala. “My dream was this vision of seeing the USA in a Chevrolet,” Winfrey said. They had every kind of experience on the road, from a game of bingo in Kansas to crashing a wedding in Tulsa.

But in the end, it wasn’t the top down, hair blowing in the wind adventure Winfrey had envisioned. “We all have big dreams and sometimes it’s better not to dream that dream,” she joked. (Aired September 2006)

Oprah confronts ‘A Million Little Pieces’ author James Frey

When Winfrey discovered that A Million Little Pieces author James Frey hadn’t been entirely truthful in his “memoir,” she promptly kicked him out of her book club, telling him she felt duped and that he had betrayed his readers.

“I sat on this stage back in September and I asked you, you know, lots of questions, and what you conveyed to me and, I think, to millions of other people was that that was all true,” she said to the author. Frey admitted he’d made a mistake, but it didn’t do much to soften the blow. “I made a mistake,” he said. (Aired January 26, 2006)

Oprah’s anti-racism experiment

In an effort to explain the dangers and pain of racism, Winfrey, with the help of diversity expert Jane Elliott, made the blue-eyed members of her audience wear green fabric collars and sent them into a room where they had to wait without food for two hours.

The brown-eyed members of the audience, on the other hand, were given doughnuts. This was a moving illustration of what racism is really like, and how easy it is for people to give in to discrimination. (Aired 1992)

Oprah talks with Mike Sisco, a gay man living with AIDS

During the height of the AIDS epidemic in 1987, Winfrey spoke with Mike Sisco, a gay man from the small town of Williamson, West Virginia, who was shamed for swimming in a public pool after testing positive for AIDS.

“The community had voiced their opinion that they didn’t want me around,” Sisco said about living in a town that shunned him. “I went through a social death… [I] wished I could hurry up and die.” The episode served as an important reminder and education for people who were unclear about how AIDS was transmitted. (Aired November 16, 1987)