In 25 seasons on television, it was bound to happen. Oprah and her team have experienced some bloopers, blunders and more than a few "What were we thinking?" moments—all caught on camera.

Whoops! Watch some of our funniest moments Watch  

For Oprah, there is one moment that clearly stands out as her most cringe-worthy. It was 1998, and The Oprah Show's 13th season was about to begin. Plans were made to unveil a sleek set design, and a new theme song would be the perfect start to the season. But who would sing it?

"We brainstormed and lo and behold, somebody came up with this crazy idea," Oprah says. "The singer of the new Oprah Winfrey Show theme song would be me."

Watch the music video for Oprah's "Run On" theme song Watch

To pull off the performance, Oprah took singing lessons and a professional choreographer taught her some moves. "Never mind that I'd never sung a note anywhere outside of church or my shower, and ignore the fact that our last theme song was performed by one of the best signers in the universe, Patti LaBelle," Oprah says. "Did that stop me? Of course not."

When "Run On," the new theme song—and its music video—debuted, Oprah says she heard the truth with her own ears. "I'd been living in a fantasy world, because one thing I now know for sure, I was really out of my lane," she says.
Cee Lo Green Remixes Run On

Oprah says it's time for viewers to forget her version of "Run On." To give the song the star power it deserves, number one chart-topper Cee Lo Green, the man behind hits like “Crazy” and "Forget You," is here to sing a ramped-up remix!

Watch Cee Lo perform his version of "Run On" Watch  

"Where were you when I needed a song?" Oprah jokes.

Meet the man behind "the voice" in this backstage interview Watch  

Kirstie Alley and Maksim Chmerkovskiy

Over the years, there's one Oprah Show guest who has never failed to entertain. Actress Kirstie Alley first appeared on the show in her pajamas, and since then, we've seen her in her bra, cleaning toilets and braving it all in a bikini.

Now, Kirstie's taking her moves to the dance floor. She and her dance partner, Maksim “Maks” Chmerkovskiy, are getting rave reviews on ABC's hit reality show, Dancing with the Stars.
Kirstie Alley and Maksim Chmerkovskiy

Though Kirstie and Maks made headlines when they stumbled and fell during an April 2011 performance, they picked themselves right up and are dancing on. Kirstie says Dancing with the Stars has been a healing experience. "It's actually been cathartic for me because I felt like I was a little broken for a while and it gave me confidence back," she says.

Her weight losses and gains have been the subject of many tabloid stories, but Kirstie says she's worked hard to lose some weight and is in a good place now. "I spent the last 10 months working on myself, spiritually," she says.

The chemistry between Kirstie and her new dance partner also helps burn a few calories. "It's like a chemical reaction," Maks says. "It might explode any second—don't be fooled."

Move aside, Jamie Foxx—with Maks around, Kirstie has forgotten all about her old crush on Jamie. "Mr. Foxx, who?" she jokes.

After the show, watch Kirstie and Maks get personal backstage Watch
Sarah Jessica Parker, Cybill Shepard and Cameron Diaz

When comedians like Jim Carey, Jerry Seinfeld and Chris Rock come around, Oprah knows she's in store for some laughs...but who knew some of Hollywood's leading ladies would make us laugh out loud the most?

Whether it's Sarah Jessica Parker losing her shoe on stage, Cybill Shepard baring her bra or Cameron Diaz chatting with Oprah about "gas," one thing is for sure—you never know what's going to happen!

When it comes to giving, Oprah says it's the thought that counts, but in this "What were we thinking?" moment, our thought process was way off.

Year after year, Oprah has delighted unsuspecting audience members with the hottest ticket in town: Oprah's Favorite Things! In November 2008, the audience took their seats and couldn't help but notice that the set was decked out for the holidays. Could it be...?

It wasn't. "This year, just bringing real meaning back to the holidays is my favorite thing," Oprah said. "And today we're going to show you how to do that without spending a ton of money."

America was in the throes of the recession, so instead of giving away high-tech electronics, gourmet goodies and designer duds, Oprah decided to show viewers how to have a thrifty holiday—and it didn't go over so well with the audience. "Our little thrifty holiday show would forever be called 'the Favorite Things that weren't,'" Oprah says.

Laura and Connie were in the audience that fateful, thrifty day. When they first saw the set, Laura was thrilled. "We thought, 'Oh my God, we made it! We're here! It's the Favorite Things Show!'" she says.

Instead of walking away with bags full of fabulous gifts, the audience got tips on how to create a $2 gratitude box.

It's been three years since that show, and Oprah Show producers still feel bad about disappointing everyone in the audience. To make amends, Oprah has a gift for Laura and Connie.

"As a token of my appreciation for the emotional roller coaster we put you through, we sent along a few of my Favorite Things to the two of you," Oprah says.

The FedEx elves come out to present Laura and Connie boxes filled with some of Oprah's Favorite Things:

Of course, Oprah didn't want a repeat of 2008. Over the past few weeks, producers have been reaching out to all 352 people who were in the audience that day. Those men and women—and today's lucky audience—are all getting three of Oprah's Favorite Things!

"There's a tote by Lands' End, a beach bag," Oprah says. "Our friends at Ugg boots sent along cute and comfy wedges for spring—those are cute. And last but not least, the Kindle 3G!"
Oprah and Tom Bergeron

That's just a taste of some of the best Oprah Show bloopers and blunders. For months, Oprah's team watched hundreds of tapes to find the top four laugh-out-loud moments in Oprah Show history, from Oprah's days as a practical joker to one producer's "un-be-weavable" hair moment.

Oprah and America's Funniest Home Video and Dancing with the Stars host Tom Bergeron are putting these hilarious moments head-to-head in the first—and last—LOL (or "Lolly") Awards.

Watch all four Lollie nominees and vote for your favorite! Watch  

"Who needs an Oscar® or an Emmy® when you can have your own Lolly Award?" Oprah says.
FROM: Oprah's Bloopers, Blunders and Funniest "What Were We Thinking?" Moments
Published on April 14, 2011


Next Story