John Kerry, Jokester
It's impossible to read Kerry's now infamous remarks without interpreting as saying that if you don't do well in school, you're going to end up in Iraq. His odd use of the phrase "stuck in Iraq" rather than "sent to Iraq" is what gives credence to the claim that it was a botched joke aimed at the president, not a comment on the armed forces. So he's so out of touch he doesn't realize that we no longer have a draft and college deferment, or he can't understand a simple line well enough to deliver it without completely screwing it up. Either way, it reinforces for Americans what a lame candidate he was, that however much they might regret that Bush is their president, they didn't have much of a choice in 2004.