20 Of Oprah’s Most Awkward Interviews Ever

Oprah’s televised talk with Prince Harry and Meghan Markle reminded us all just what a class act she is. But not every interview conducted by the talk show legend has gone so smoothly. From inappropriate jokes to interrogating fans, here’s a look at 20 times Lady O’s chats made us want to hide behind – rather than jump up and down upon – our sofas.

20. Oprah calls out Barbra Streisand’s diva demands

Barbra Streisand sure lived up to her diva reputation in 2003 when she paid a visit to Harpo Studios. The Yentl star famously rocked up in an all-ivory outfit that matched the color of her lapdog. And the singer even insisted that the microphone she used to perform a musical number be spray-painted to complete the uniform look.

Perhaps to Streisand’s surprise, Oprah let audiences know about this bizarre demand. The “Woman in Love” singer then defended herself, responding, “I like simplicity and monochromatic frame. So I thought, just look, if the mic melts in my sweater... In other words, it just makes the focus on the song.” That was Lady O told.

19. Oprah describes James Frey as a “false person”

James Frey found out the hard way that you cross Oprah at your peril when he accepted an invitation to appear on her show in 2006. The author’s autobiography A Million Little Pieces had previously been selected for the host’s prestigious Book Club. But just three months after it shot to the top of the bestseller’s list, reports emerged that Frey had told several porkies about his harrowing life story.

It’s fair to say that Oprah wasn’t happy about inadvertently recommending someone she described as a “false person.” She told Frey, “I feel that you conned us all. Do you?” The chat show legend later said sorry to the writer for her character assassination. In fact, she asked him back to Harpo Studios in 2011 where she acknowledged that the book, fabricated in parts though it may have been, had still inspired those struggling with addiction problems.