The Most Uncomfortable Oprah Interviews Ever

The Oprah Winfrey Show remains the highest-rated daytime talk show in the history of American television. It ran for 25 seasons and has created some of the most heartfelt and culture-changing moments on TV.

Winfrey is known to be a skilled interviewer and has conducted some intimate and thought-provoking conversations on her show. However, no one is perfect and there have been some uncomfortable and awkward interviews as well.

We’ve compiled a video that lists some of the most uncomfortable interviews ever done on Oprah's couch. Think you know who is on this list? Watch this video and find out if you are right!

#Oprah #OprahWinfrey #OWN

Barbra Streisand | 0:00
50 Cent | 1:09
James Frey | 1:58
Lance Armstrong | 2:52
Mackenzie Phillips | 3:52
Elizabeth Taylor | 4:35

[NickiSwift]

What do you think was the most awkward Oprah interview moment ever?

[Paranidchick]

The problem with interviewers like Oprah they get famous and they start forgetting the essence of a professional interview is being objective

[jefftay]

Please show more of the clips instead of just talking about it

[theophaneantipater]

I'm waiting an interview of Oprah about Harvey Weinstein friendship That would be unconfortable too !

[eggsheran]

why is the MJ interview not here?! she asked mj if he was a virgin. and accused him of bleaching his skin?!
oh yeah right, oprah deleted it after the air of leaving neverland

[sammbabazi]

I remember Whitney Houston telling her off, "none of your business" back in the mid nineties😂😂

[billyboylb]

I love the Streisand piece. Oprah: So you had the mike spray painted. Barbra. That's right!

[robertb]

I was a very poor child in Brazil. and Elizabeth taylor was my godmother. I would like to thank you for everything you have done for me and my family. or her children. thanks for everything.

[summerbabetoo]

Ms. Taylor was trying not to die laughing at whatever that was on Oprah’s head😂😂😂😂. That affected her more than the pain killers

[janemills]

Oprah has always made me feel uncomfortable, she's too smug and looks down her nose at people. Lovely Elizabeth saw through her.

[edwinlobos]

Jennifer Hudson was super awkward. She should have been on the list. Lindsay Lohan was awkward too.

[mrgordy]

I think what’s awkward is Nicki Swift never shuts her big yap for two seconds so we can hear the interviews in question.

[larryk]

He killed me when he said I didn't call you fat🤣🤣

[nhotwings]

The clip with Elizabeth Taylor is never even shown. I thought we were supposed to "experience" it. Lol right.

[marcirobins]

The Elizabeth Taylor interview was work! Ms Taylor owned that interview.

[richardandretti]

Elizabeth Taylor showed Oprah who had the upper hand. I miss you, Miss Taylor.

[SWSimpson]

I loved Elizabeth Taylor. She changed the world, she quite literally did, and I am grateful to her for that. No, I'm not talking about her movies. Not a lot of people can say they rocked the world a little bit in their lifetime, but she moved it.

[mayhampson]

Is there someone out there who feels the same as myself, I cannot understand why Opera Winfrey earned so much money and was so popular on her TV inter views, can any one tell me .?..

[zenomorph]

It doesn’t matter who she interviews, I cringe.

[joanie]

He named his dog Oprah how bloody hilarious.