Oprah Says This Was the Worst Guest She Ever Had

The generally amicable host spilled some tea, and revealed how she turned the interview around.

In Oprah Winfrey 's25 seasons and more than iv,500 episodes of The Oprah Winfrey Show, she interviewed thousands and thousands of people, from the biggest stars to self-help experts to everyday people. Of grade, all interviews are not created equal, merely Winfrey tends to stay on the positive side of things when looking back on her fourth dimension at Oprah. Even so, when she was onHarry in 2017, hostHarry Connick Jr. was able to clasp out some previously undisclosed information from the prolific interviewer herself. He even got Winfrey to talk nigh her nearly unsavory guest experiences. While she wouldn't name names, Winfrey did say the worst guest she had on Oprah was someone far less loftier-profile than you'd imagine. For more on Winfrey's worst guest, read on. And for another disastrous interview to remember, bank check out The Worst Guest "Today" Has Ever Had, Host Says.

"Has anyone been particularly abrasive, where you're simply like, 'Gosh, I tin't wait for this person to leave?'" Connick Jr. asked. "Well, you know, the worst kind of guest—yous've had this, too—is when you lot ask them question and they start talking nearly 1975, and and so you think, 'Oh, we are in 2017. How long is it going to take us to get to 2017?' That's the worst," she responded. All the same, that wasn't all she had to say on the topic.

"The other worst guest, for me, are those who think whatever it is they're talking almost is then spectacular, and yous know information technology'due south not," she said. Winfrey admitted that her "get-to discussion" for guests like that was just a elementary—but seemingly inauthentic—"wow!"

She then went on to describe her truly least favorite guest experience, pointing to a lawyer who had gone on Oprah to promote his book. And promote it he did. "He mentioned the volume 29 times. That's after I started counting," Winfrey explained. "Every judgement started. 'In my book, in my volume, and if you lot buy my volume.'"

Winfrey said she finally got fed upward with the cocky-promoting lawyer and called him out. "Finally, around the third segment, I said, 'Nosotros all know the proper noun of the volume. Audience, tell him the proper noun of the volume…so you don't accept to say the name of the book anymore,'" said Winfrey. Luckily the interview turned around from at that place. "After that, we started having conversations."

Here are more guests who had an awkward experience on The Oprah Winfrey Bear witness, and for the most infamous voice to utter, "Live from New York, information technology's Saturday night," bank check out The Worst "SNL" Host of All Time, Cast Says.

tom cruise, was newspaper carrier
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Who could forget when Tom Cruise spent his time on Oprah gushing virtually so-girlfriend Katie Holmes? In the interview, you can tell Winfrey doesn't know how to react to Prowl'south over-the-summit excitement, which leads him to jump on the couch and catch both her hands and shake her. And for an update on Cruise'southward family, This Is What Nicole Kidman and Tom Cruise's Kids Together Look Like Now.

James Frey author of "A Million Little Pieces" on Oprah
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The writer ofA Million Little Pieces, James Frey, brought out a rarely seen side of Winfrey. The host eviscerated the writer afterwards it was revealed that he had fictionalized much of his alleged memoir, which she had included in her signature volume club. However, the two later cleared the air and had a positive discussion. And to find out which of your favorite celebrities don't stack up in person, check out An Airport Employee Rates Celebrities Based on How Rude They Are.

Drew Brees
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The whole audience was cringing when Winfrey mistook Drew Brees'birthmark on his face for leftover lipstick from a kiss. Trying to be a good host, she attempted to wipe the marker off his face up. And for more glory content delivered straight to your inbox, sign up for our daily newsletter.

Jay Leno
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Winfrey laid into Jay Lenoafter he was booted fromThe This night Showmerely to return and kick Conan O'Brien out of the coveted slot. Her searing questions included: "Were you embarrassed most how all of this transpired?" "Did you lot e'er ask yourself, 'Am I existence selfish?'"and "Exercise you think celebrities will all the same come on your show or pass up to come up on your prove?" And for the stars who prefer to keep to themselves, here are 17 Major Celebrities Who Actually Hate the Spotlight.