Looking back over the years, Oprah says there have been a handful of moments that simply make her cringe! Topping that list of embarrassing moments is the time Oprah dressed up as one of her biggest heroes, Diana Ross.
As a girl, Oprah loved to watch Diana Ross and the Supremes on the Ed Sullivan Show. "I used to stand in front of the bathroom mirror with my brush and pretend I was Diana Ross," Oprah says. "I should have stayed there in front of the mirror with the brush!"