Oprah Winfrey Reveals the Worst Guests She Ever Had on The Oprah Winfrey Show

Harry Connick Jr. interviews the TV titan for a full hour on Monday's episode of Harry

By Zach Johnson Nov 06, 2017 2:00 PMTags

Oprah Winfrey thrives on meaningful conversations.

For 25 years, she interviewed everyone on The Oprah Winfrey Show, from reality stars to royalty. But, as she reveals on Harry Tuesday, not every conversation had its aha moments. "You talk about all of the guests you've had over years," Harry Connick Jr. says. "Has anyone been particularly annoying, where you're just like, 'Gosh, I can't wait for this person to leave?'"

"Well, I mean, the worst kind of guest—you've had this, too—is when you ask them question and they start talking about 1975, and then you think, 'Oh, we are in 2017. How long is it going to take us to get to 2017?' That's the worst," says Winfrey, who was on the show to promote her latest book, The Wisdom of Sundays: Life-Changing Insights from Super Soul Conversations. "The other worst guests, for me, are those who think whatever they are talking about is so spectacular, and you know it's not. So, my go to word was always, 'Wow.' Like, 'Wow! Really?'"

But the "worst" kind of guest is the self-promoter, she says.

Paul Zimmerman/NBCUniversal

"I had a guest on who was a lawyer—I can't remember the show—and he mentioned the book 29 times. That's after I started counting," she says. "Every sentence started. 'In my book, in my book, and if you buy my book,' and so finally, around third segment, I said, 'We all know the name of the book. Audience, tell him the name of the book…so you don't have to say the name of the book anymore.' After that we started having conversations. Our intention was to tell the people, 'You don't have to sell your book. I will mention the book. I will take care of the book.'"

During his hour-long interview with Winfrey, Connick also talks to her about how success can change people. "I would be this person [no matter what]," she insists. "It's wonderful the way my life has worked out and that I'm really rich and everything. That's real cool. I really like that."

"You know how rich you have to be to say it like that?" Connick teases, as it's no secret that Winfrey is one of the wealthiest people alive. "You have to be really rich to say, "I'm really rich."

"Yeah, but I'm not one of those people who ever [lied about being rich], because I used to hate it when really skinny women would come on the show and complain about their thighs: 'Girl please!'" she says, noting that it's silly "for people to act like they don't have stuff when they have it." While having money does add "a certain level of comfort," she says, it's ultimately not what matters most. "This is the real truth: Wherever you are in your life, if you win the lottery, you will still be the same person. You will still be the same person," she says. "That money and those things you will now be able to buy are just a magnifying glass on who you already are."

To find out when Connick's interview with Winfrey airs, check your local listings.