Douglas Wambaugh - Picket Fences
Douglas Wambaugh lives up to every negative stereotype about lawyers -- and he's proud of it. His total lack of ethical boundaries and over-the-top courtroom persona are good for a laugh (and sometimes effective), but he'd be too much to take in a social situation.
Lieutenant Provenza - Major Crimes
Lieutenant Provenza is two parts curmudgeon, one part brilliant investigator. His sarcasm hides a sensitive streak, but it could get irritating to hear him rant about... well, everything, especially the Internet, teenagers, and the dumb criminals that consume most of his attention.
Lou Grant - The Mary Tyler Moore Show
Lou Grant was the kind of boss that might make modern-day viewers cringe, but the crusty, alcoholic exterior juxtaposed with a sensitive interior made for great comedy. Unless your thing is drinking him under the table, you might not enjoy hanging out with him very much.
Blanche Deveraux - Golden Girls
Blanche's insatiable sex drive and Southern belle attitude occasionally annoyed the rest of the Golden Girls and drove her daughter insane. Could you imagine hanging out with her? The sex jokes would get old after a while, and what else would there be to talk about?
Mr. Kimball - Green Acres
Almost everyone in Hooterville was weird in some annoying way, but Mr. Kimball was the funniest -- and the most irritating -- of the characters in this classic comedy. He wasn't able to finish a sentence without going off on a tangent that made no sense to anyone but him, so how could anyone possibly hang out with him without losing their mind?
Dr. Cox - Scrubs
Dr. Cox was the epitome of the most nightmarish teacher/boss anyone ever had. His sarcasm, cynicism, and refusal to follow orders were a fascinating combination of irritating traits that somehow made for great television. Why JD was so desperate for his friendship is a mystery, since he was exactly the kind of guy that no one wants to hang out with.