Great topic thier OS- one of my all time faves. Having been a stand up comic for over 15 years now- I would have to say that comics, and I have talked to hundreds, some super famous now, some not so well known- I will tell you a couple things I have found- comedians are left leaning libertarians for the most part, and conservative comics are usually not funny nor famous. During the Clinton era, he wrote the material for us, even if we agreed with him- which is point number two- we are all whores for a laugh. That is the term we use, so we are not offended when others tell us this either

- also- we, as a group, are far less politically correct amongst ourselves, and racial lines are non-existant. Typically, you get three comics in a room, the one-uppmanship on politically incorrect jokes that would NEVER go over well on stage happen in those groups. Really nasty, disgusting, racist, sexist jokes are told, followed with the obligatory "I am so going to hell for that last joke" and the Jerry Sienfeld created "hey, are we supposed to be talking about this?"
What interesting Comedic lines have you come across that are not just funny, but compelling, and why?Lenny Bruce, Goerge Carlin, Richard Pryor are the all time greats of observation comedy, political commentary, and created the post-henny youngman vaudvillian observation stand up comic, with, to a lesser degree, Bill Cosby. Though he is great too, he is basically pretty vanilla, but he was/is still a great man with great comedy, just not so edgy or political as the others.
I think Dennis Miller has been ostrasized, a bit unfairly, over his conservative stances, though, he did explain he was a right leaning libertarian. I think his points and observations, even if I did not totally agree with them, were fair, insightful and balanced, not to mention good delivery, timing and just plain good material. Bill Maher was/is a genius, but the best of all time, regardless of political viewpoint, Al Franken is almost revered by all comics, for his INCREDIBLE political comedy writing. Possibly the best ever, and recognized as so by his peers. Robin Williams is the most hated comic by other comics of all time BTW- They call him "Robbing" Williams- for his over the top delivery of stolen material. His so-called political commentaries/jokes are NEVER his own- he has lifted them piecemeal from others. When this was pointed out to me, early in my little career, I started watching him closer, and sure enough, he is a material stealer!
I have opened for Lewis Black many times, and he is spot on in both his observations and his anger. He is a personal friend and we chat now and again.
And that brings us to what may prove the greatest of all time political commentator- John Stewart. Nuff said!
Bonus: What Comedians do you feel are the best and this, and what Comedians do you feel go to far with it? And Why?Al Franken, Bruce Wallanch, Goerge Carlin and Bill Maher are pretty much recognized by thier peers as the best at this genre of comedy, no matter your personal views as a comic. Also- a comic will critique another comic- NOT on his/her political views, but how it is delivered, how crisp and original the material is, and how it connects with ALL audiences.
There is NO such thing as "to far with it"- just parochial poeple of small minds and big egos that don't have a sense of humor. Acknowledged universially, conservative or liberal, dem or republican, as the very worst political entetainer of all time would be Rush. He basically stole his format from Howard Stern, and he has 0 crossover appeal, a "niche" audience. "niche" audience political commentators are pretty much considered the bottom of the barrel in material, delivery and style, no matter how large thier niche audience is, no matter how much money they make. Think like musicians here, sure, the pop artist made some big record sales, but that doesn't mean it is good, or original, or even thier own material, it just means alot of poeple bought it.
John Stewart may very well prove to be the best ever, we will see how his show winds down in a few years to really comment on it- but at this time, he has no peer, with the possible excepton of bill maher and al franken.