1. Stainmaster Oprah. February 11, 2010.
Oprah tried to wipe off Drew Brees’s Birthmark, mistaking it for lipstick.
2. Suprem-O. February 25, 1993.
Oprah dressed up as one of her biggest heroes, Diana Ross.
3. She's our private dancer. May 1996.
Oprah rocked her Tina Turner wig—for years.
4. Crusin' for a bruisin. May 23, 2005.
Tom Cruise's bizarre behavior on Oprah's show (jumping on her couch and declaring his love for Katie Holmes) was not only an embarrassing moment for Cruise, but the incident left Oprah speechless.
5. One last squeeze. December 1988.
After four months of extreme dieting, Oprah entered her studio wearing slim designer jeans and pulling a wagon onto the stage filled with 67 pounds of fat, to symbolize the amount of weight she lost. After that one day, she has never fit back in those size 10 jeans.
6. O no you didn't. January 26, 2006.
Oprah selected James Frey's A Million Little Pieces for her book club in 2005, which then became an instant best-seller. After the revelation that many of Frey's stories were fabricated, Oprah invited Frey and his publisher on her program. Oprah admonished Frey in front of millions of viewers, an embarrassing moment for which she later apologized.
7. Kentucky fried shortage. May 5, 2009.
Oprah tried to help Kentucky Fried Chicken’s promotion of its new grilled chicken by offering free meals to everyone. Anyone who could download a coupon off her website could redeem two pieces of chicken, two sides and a biscuit. KFC had to withdraw the offer, because chains ran out of food and the lines were too long to handle.
8. Tissue Stuffing. June 2006.
On Oprah’s website, she shares some unscripted moments that never made it on air. Moments before introducing Desperate Housewives star Teri Hatcher, Oprah’s stylist came on stage to point out something white coming out of Oprah’s top. She responded, "You know what this is…this is my tissue!" Oprah says, "No, I was not stuffing my breasts. Believe me—I have enough." The tissue was meant to be under her armpits to protect her top from deodorant marks.
9. Oprah's va-jay-jay. February 2007.
It wasn’t an embarrassing moment so much as an embarrassing conversation. Oprah wanted to know what women from different parts of the country called their “va-jay-jay.” Oprah heard the new slang word on a Grey’s Anatomy episode. Oprah's conversation with her audience members helped “va-jay-jay” enter the hallowed halls of the Urban Dictionary.
10. Pantyhose fiasco. Oscar season
According to her site, Oprah says she once made the mistake of wearing pantyhose that were too tight to an Oscar party. Being too tight, they would roll down. Oprah recounted, "You're sitting talking to some famous person, and you can feel them rolling. Then when you move, they roll some more. Honest to goodness, I remember getting up and they were down to my knees!"