6. Trebek's "Hurts To Miss That One" Moment
No one is at fault here. It's just really, really awkward. An Indian-looking man bets all his money on a question to which the answer is New Delhi, reacts with a pained face and gets the Trebek line, "Yeah, hurts to miss that one!" Why does it hurt so bad Alex? The money thing, yeah. We guess... but there's a tiny little voice at the back of our heads that screams racism. Especially when you consider the contestant only had a thousand bucks to gamble with. Oh so just because he's brown he should know everything about India? The answer is tolerance, Mr Trebek. As is the nature of Jeopardy, the game immediately moves on and everyone is left with their thoughts. We like to think that Alex Trebek was asking himself whether he really just said that. Simply because the idea of his stoicism almost being broken tickles us.