Trinsky,
During one of Charlie the Drug Addict's recent calls, he went off on how he got arrested, etc, etc., but then he threw in there that he had gotten terribly injured during something and it was sort of overlooked, but he sort of really emphasized how badly he had been hurt and I just thought it was such a sad moment and would be a perfect clip to find. He's my vote for Saddest Caller, definitely.
Samir--caller of the year!