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20 worst Oprah moments

Mallory Hoke

ChicagoNow Life & Style Community Manager

With the recent announcement that Oprah will be retiring, we decided to celebrate by highlighting O's 20 worst moments. Feel free to add in any that we missed, and  let's party like it's 2011 already. Click through the photos below for Oprah's most awful: 



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EB said:

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Thank you for this! I love this "real" perspective.

kell99 said:

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This is the dumbest story I've ever seen. Obviously whoever was responsible for this was searching for news. Oprah's confidentiality contract scandalous? Who cares. She's a talk show host giving her opinion. This article gives journalists a bad name and is obviously aimed at unintelligent people looking for something to be negative about. Get over it.

EB said:

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sorry, you're wrong. as a huge (ha!) public figure, oprah is open to this kind of scrutiny, and she's had her fair share of screwups, including endorsing (however implicitly) fraudlent products. This was an enjoyable feature.

jschaeff1985 said:

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Plus anyone who promotes something as dumb as "The Secret" deserves all the derision they can get.

dude said:


Twenty reasons not to watch Oprah...I guess.

ChipSet said:

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Ummm. "The feud began after a failed joke at the Academy Awards in 1995. Oprah vowed to never appear on Letterman's show again. They 'buried the hatchet,' 16 years later."

They buried the hatchet in 2011?

Conspiracy Man said:

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No Jonathan Franzen?

Calvin Coolidge said:

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It's true -- Oprah has stumbled a few times in 25 years, most often when she gets wrapped up in her (exaggerated) perception of her own significance or when she allows her credulity in the areas of spirituality/alternative medicine/etc. to cloud her judgment about what to present to her even more credulous audience. But if these really are her 20 "worst moments" over 25 years and who knows how many shows, I'd say she's done a pretty good job.

In fact, I'd argue that one of her so-called worst moments was, in fact, one of her best: when she took on the Texas cattlemen in that lawsuit. She was so in the right and they so in the wrong. Not only did she strike a legitimately righteous blow for free speech in the face of Texas's thuggish law allowing people to be sued for "food disparagement", she also turned it into a brilliant public relations coup for her and her show.

Say what you will about her but at the end of the day, she's a terrific entertainer.

wedding said:


I think these 'worst' Oprah moments just show that she's human. Yeh she's made some mistakes , yeh she's been misled by people she trusted, and yeh she's changed her opinions, but how many of us wouldn't do that over the course of 25 years? She brought more positivity to the world and that is what really matters.

IrishSweetness said:


Selling political lies wrapped in a black face to her dumb public was unforgivable. Watching all those Jay Zees and Oprahs selling 'Obamanomics' is just pitiful. Shame on them. The country has been bankrupt since 1933, we have our worst recession since then, and what does he do ? He prints $800 million to 'stimulate' the economy ... flying in the face of a couple of hundred years of economic thought. Getting further into debt to get out of debt? Sounds crazy, doesn't it ? Because it is ....

Sasha Davis said:


Don't forget about Tom Cruise jumping on the couch!

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