25 Years of Laugh-Out-Loud Moments

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   

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?