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I can't think of a "worst" experience, but I've gotten more than a little annoyed when people at con games try to engage me in pointless chit-chat while I'm trying to become engrossed in a game. That's happened more than once.
That has to be a CoC scenario I participated in at Origins 2007, with my wife and a number of hardcore CoC groupies. It was the last day of the Con and our four hour event became an eight hour session. It was an extremely immersive game.
Over the years I've found a couple of groups that I've actually clicked with. Although, more recently, I haven't been able to find any groups that were interested in the same games I wanted to play.
Some of the most phenomenal role players that I have met have been women. I think we should encourage more women into the hobby. As a black gamer I'm all about diversity at the game table.
This list isn't in any particular order, but my three are Call of Cthulhu, because I'm a big fan of the Mythos... Kult, because of the Clive Barker, Hellraiser, vibe it has going for it... and finally, any of the World of Darkness settings.