5 of 15
The Perfect Dress
In 1997, Oprah and Gayle were both attending the Primetime Emmy Awards—and Oprah didn't want Gayle raiding her closet for something to wear! To keep her best friend at bay, Oprah tasked the audience with the job of picking out Gayle's dress. Gayle looked on via satellite as the audience reviewed five different gowns; a black halter dress by Fred Hayman won out in the end.