Oprah’s 9 Most Embarrassing Moments

American Icons, Celebrities, Celebrity Q&A, Featured Article, People
on January 27, 2014

To commemorate the queen of daytime talk’s 60th birthday, we’ve compiled a selection of Oprah Winfrey’s most embarrassing moments. From brawling with the beef industry, to chastising accomplished authors, Oprah is no stranger to the uncomfortable.

1. Va-jay-jay, Oprah circa 2007

Oprah Shocked

Courtesy of Paste Magazine

The conversation that launched a thousand va-jay-jays: Oprah’s “Grey’s Anatomy” reference prompted a query for what women across the nation call their nether regions. TMI, Oprah, TMI.

2. Oh, honey, let me just wipe that birthmark off for you, Oprah circa 2010

Drew Brees

Courtesy of Oprah.com

In a gesture of motherly concern, Oprah attempted to wipe a foreign substance off the face of New Orleans Saints quarterback Drew Brees. That foreign substance was his birthmark.

3. A million little lies, Oprah circa 2006

James Frey

Courtesy of Oprah.com

After Oprah featured author James Frey’s “A Million Little Pieces,” she felt the need to publicly chastise him for fabricating parts of his book. Frey recoiled as Oprah reminded him that no one pulls one over on Queen O.

4. Denim desperation, Oprah circa 1988

Oprah Jeans

Courtesy of Oprah.com

All-star chefs and celebrity trainers couldn’t make up for Oprah’s lack of old-fashioned willpower. After four months of extreme measures to fit into size 10 jeans, Oprah fit into them for one day only. By the way, she’s toting 67 pounds of fat behind her to represent her weight loss.

5. Tina Turner impersonator or talk show maven? Oprah circa 1996

Oprah Tina Turner Wig

Courtesy of Oprah.com

For years, Oprah rocked a wig that would stop Proud Mary dead in her tracks. Longtime partner Stedman Graham finally encouraged her to do less Tina, more Oprah and ditch the wig.

6. Impersonator round two, Oprah circa 1993

Oprah Diana Ross

Courtesy of Oprah.com

Oprah grew up pretending to be Diana Ross, and being a syndicated television host allowed her to take the obsession one step further. She dressed up as the diva and gave it her best shot on national television, only to regret it later.

7. Grumpy Elizabeth Taylor, Oprah mid 1990s

Oprah Bad Hair

Dealing with a curt Elizabeth Taylor is one thing, but showing up without a perfect coif only adds to the drama. Not only did Oprah stumble through the interview, but she also looked a little road weary.

8. Salvation according to Oprah, Oprah mid 1990s

New York Hilton Hotel

Courtesy of Biography.com

Want to get people hot and bothered? Talk religion. Then dispute the existence of God, or number of Gods. Oprah incited national rage with this segment.

9. Where’s the beef?, Oprah circa 1996

Oprah Beef

Courtesy of Oprah.com

Cattle ranchers and the collective beef industry lost a little love for O and quite a few dollars. After a show on mad cow disease and the dirty details of American beef, cattle ranchers took Ms. Winfrey to court for defamation.