Howard Stern may be the king of all media, but Winfrey is definitely the queen. This talk-show host/actress/magazine publisher/Broadway and Hollywood producer/studio mogul/philanthropist is consistently cited as one of the entertainment industry's most powerful people. Winfrey worked as a news anchor in Nashville and Baltimore before becoming the host of Chicago's morning talk show in 1984. She was so popular that the series was renamed in her honor and became a national hit in syndication in 1986. Oprah quickly became a household name, a wildly successful yet still accessible woman who struggled with her weight and talked about surviving sexual abuse. Every year, Winfrey seemed to tackle a new business venture, rarely making any missteps, and winning a multitude of awards for her efforts. Although the couple never married, she has dated Stedman Graham for decades.