5. Rosie O’Donnell — Comedian
The comedian formerly known as the Queen of Nice has undergone a major transformation since the days of her talk show, Rosie, which ruled the daytime airwaves in the mid-1990s. In years immediately following the end of her talk show, O’Donnell underwent more than her share of bad press and had to deal with fallout from the failure of her magazine (and the lawsuit that followed), the failure of her Broadway play Taboo, and the failure of her haircut. But in 2006, she returned to the media spotlight by landing a gig as co-host on Barbara Walters’ The View, where she upped the ratings by 27 percent from the year before.
In the four years between Rosie and The View, O’Donnell also came out as a lesbian, advocated for the rights of gay parents, launched R Family Cruises with her partner, Kelli O’Donnell, married Kelli on the steps of San Francisco City Hall in February 2004, and became a blogger and artist. As if that weren’t enough to keep her busy, last fall O’Donnell made a guest appearance on Nip/Tuck that led to rumors that the show would launch a spinoff based on her character.
But despite her recent successes, O’Donnell has continued to be spotlighted negatively in the media due to her outspokenness â€” something that thrills gay activists when she talks openly about her same-sex marriage on The View, but is upsetting when she inadvertently makes racist comments in the name of comedy. "There are people who think that I’m strident and bossy and much too New York and left-wing liberal," she told Newsweek last September. "You get what you paid for, and there’s no way that I’m going to change."