Rosie O'Donnell

Although these days she's an out lesbian and tireless advocate for gay rights, there was a time when this full-figured comedian was simply known for being funny. After a winning streak on Star Search, this tomboyish stand-up brought her brazen attitude and Long Island accent to a host of TV series and films (a one-year stint on Gimme a Break!, A League of Their Own, Sleepless in Seattle, The Flintstones), usually as a bighearted, acid-tongued second banana. In the mid-'90s she made a decision that would change her career: Tired of working long hours on movies and anxious to spend more time with her adopted son, O'Donnell launched her own eponymous daytime talk show in 1996. An instant hit, the series cast the formerly brash comedian in a new role, that of Rosie "The Queen of Nice" — a show-tune singing, Tom Cruise-loving, down-to-earth everywoman, who effortlessly connected with folk across America. During her tenure, she won a bunch of Daytime Emmys, hosted a number of award shows (the Tonys, the Grammys), launched a magazine and even starred in the Broadway musical Seussical. But 2002 marked another change in trajectory for the star. After years of speculation about her sexual orientation, O'Donnell officially came out as a lesbian and soon after resigned from both her magazine and TV show to spend more time with her partner, Kelli Carpenter, and their ever-growing family. She was still never completely out of the spotlight. In 2004 in the midst of the ongoing debate over legalizing gay marriage, she and Carpenter wed in San Francisco. The couple also founded a gay family-friendly travel company, which was chronicled in the documentary All Aboard! Rosie's Family Cruise. In 2006, O'Donnell returned to daytime TV after a four-year hiatus as the most outspoken member of the chatfest The View. Although she only stayed with the show for a year, she helped boost ratings with her blunt banter, public feud with Donald Trump and frequent clashes with her conservative cohost Elisabeth Hasselbeck. In May 2007, a particularly heated political debate with Hasselbeck prompted O'Donnell to exit the talk show almost a month earlier than previously announced.