3. Adam Sandler in Happy Gilmore, Billy Madison, Mr. Deeds, Click
In real life, Adam Sandler is a world-famous multimillionaire celebrity. But in Happy Gilmore, he was a hockey player who couldn't cut it with an anger management problem. And yet he managed to get with Julie Bowen, who despite in the film suffering from a dreadful condition called "Nineties Hair" is now one of TV's favorite hot moms. In Billy Madison, he hooked up with his hot teacher. 'nuff said. And in Mr. Deeds, he got with Lydia herself Winona Ryder. But being married to Kate Beckinsale in 2006's Click takes the cake. She's so good looking there are some countries that worship her as a diety. Christ, she's so attractive I watched the movie Serendipity.