Aside from the problems once again with voting machines, a group of voters from both Connecticut & Florida deserve the award for stupidest election choices.
Florida-- Former Republican House leader Mark Foley was for to resign from the House of Representatives in September in his male pages. He still managed to get 110,000+ votes (48%) for and barely missed being re-elected.
Connecticut-- Senator Joe Lieberman lost his bid to defend his own seat for the Democrats in the recent primaries. Rather than give up his seat he choose to give up his party instead. He managed to gain 50% of the votes to clearly defend his seats. Way to go Democrats.