Obama: Ice-Cream Scooper
Obama’s very first job was scooping ice cream at a Honolulu Baskin-Robbins (you know, the one on 1618 South King Street?). He later described the brutal conditions he endured: "Chocolate ice cream gets real hard,” he has said. “Your wrists hurt. [Carpal tunnel syndrome, although] they didn't call it that.” That’s not the only reason he considers this his worst job—he ate too much ice cream and, consequently, doesn’t like it anymore.

McCain: Ensign
When he graduated from the Naval Academy in 1958, McCain was commissioned as an ensign and spent two and a half years as a naval aviator training in Pensacola, Florida, and Corpus Christi, Texas. Stationed in Texas in 1959, years before he would crash into Truc Bach Lake in Hanoi and be captured by the Vietcong, a plane McCain was flying experienced engine failure and wound up at the bottom of Corpus Christi Bay. Knocked unconscious, McCain was barely able to swim free of the plane but escaped serious injury and was able to attend to his social obligations (read: partying) that night. McCain liked flying, but he loved the aviator lifestyle: During this period he organized parties, drove a Corvette, and dated numerous flashy women—including a dancer named "Marie, the Flame of Florida" who enjoyed terrifying the naval wives by cleaning her nails with a switchblade.