Preloading
O
Print
25 Years of Laugh-Out-Loud Moments
Relive some of The Oprah Winfrey Show's funniest bloopers, blunders and "What were we thinking?" moments!
Oprah
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?