OK, so I get #1: He's incapable of empathy! Or just "crazy"! And #3: He's a jerk! And/or easily manipulated! Unworthy of respect! And possibly other senses of the word!

#2: She's... a woman? Help us out, OED: "A woman who is regarded as naturally predacious in her search for or treatment of lovers." So, she sexually harasses her male subordinates? I sort of can't imagine a version of this image with a good-looking man (labeled, say, "Skirt-Chaser") looming over a cowering female employee and grabbing at her clothes. That's just illegal. But a woman—that's comedy! Even AWESOME! Bonerfest 2011! Michael Douglas and Demi Moore 1994!

p.s. I can't believe a four-man crew was hired to paint this sign.
p.p.s. Jennifer Aniston???