William Penn, who founded Philadelphia, once remarked "Where wisdom has wit to express it, now there's the best orator." So, is there a place for wit and/or humor in the halls of Congress or in the office? And what quotes, if any, do you have to support your claim.

Yes, humor has a place in politics, as long as it's funny. I support and supported Obama, but he's not funny. He should not try to make jokes. (Let's remember the "Special Olympics" and lackluster performance at the Alfred E. Smith Memorial Dinner.)
Now, McCain, there is a funny guy. Of course, the most recent Bush could provide some laughter from time to time as well. My sisters-in-law have as a permanent fixture on their refrigerator a button with his face on it and his quote "The most important question in education is, is our children learning?"
This is a fascinating topic, by the way, for a Japanese friend of mine. The relationship between the people and their politicians there is much more serious; perhaps because the press is much less critical. (For interesting reasons. See http://www.onthemedia.org/transcripts/2008/12/12/06 if you're interested.) Anyway, my friend, who arrived to the US in 2007, thought the Bush bashing was hilarious and couldn't get enough of it. He has a collection of calendars, books, and other realia that makes fun of our illustrious ex-pres.