Best Political Challenge - 2004
John Hickenlooper v. Tony Young
You'd think that besting seven other candidates in the mayoral race would be enough for John Hickenlooper. But you'd be wrong. Denver's new mayor is always up for a challenge. During his campaign, he promised that he'd visit a Denver school every week, and while in an elementary-school gymnasium on one of those visits, he spotted a set of climbing ropes hanging from the ceiling. On the spot, he challenged mayoral aide/driver/much younger guy Tony Young -- and then proceeded to win a race to the top, while amazed students cheered below.