I love stand up comedy. Love it. Even when it's bad, I still love it.
The problem I often run into is that the more socially inappropriate the comedian, the more I tend to love their routines. If their material makes me nervous, I know they are doing something right. Something about the fact that they understand the comedian's role as the jester...the one who can relieve social pressure by saying the things we cannot in our "normal" lives (whether we want to say those things or not)...that's what I love.
So here is a quick sampling of some of my favorite performers and routines by them that I love. True to form, some of it may offend, some of it may be down right horrible--and, again, not that these are things I want to say--but these comedians are interesting for taking the chances, and taking the jester role seriously (as oxymoronic as that sounds):
Kathleen Madigan from her tour in support of her album "In Other Words"
(* not work safe)
Daniel Tosh from his special "Completely Serious." Now, forwarned is forearmed; he says some truly terrible things, but his whole point (and he says it in an earlier part of his special) is to start with a joke that is fairly acceptable, and then push it and push it until only 6 people find it funny. In this particular section, the metacomedy is amazing.
Dmitiri Martin from his special 2007 special "Dmitri Martin: Person"