Bill Clinton, saxophonist

Kevin Winter, Getty Images

Bill Clinton endured several public-image issues over the course of his career, but during his 1992 presidential campaign, he was playing all his cards right. His popularity shot through the roof when he appeared on 'The Arsenio Hall Show' clad in a black suit and Ray-Bans, armed with a saxophone and ready to rock. After he rather adeptly navigated Elvis Presley's 'Heartbreak Hotel,' Arsenio joked, "It's nice to see a Democrat blow something besides the election." We're guessing Clinton doesn't find that joke so funny anymore.