True story: In 1993, I got my job as a White House correspondence writer largely based on my successful drafting of a message from Bill Clinton roasting his new White House Counsel, Bernie Nussbaum. I don't know if Clinton ever actually saw what I wrote, but it played well around the office and was apparently well received by Nussbaum. The leaders of the correspondence office liked what they saw and offered me a staff position.
That successful moment aside, I really hadn't captured Clinton's sense of humor. I wrote what I thought would be funny, informed by my own white urban Jewish upbringing; I really hadn't seen enough of Clinton's jokes to have a sense of what he would have said. His sense of humor, as I would later learn, was similar to that of many of the other Arkansans I was working with. It was a bit more insult-based. (The Arkansas I've known really like insulting people's mothers. This put me off at first, but I've grown to love it.) Comedy writer Mark Katz, who got hired to write a speech for Clinton, wrote a lengthy article in the Washingtonian about the different joke styles, and how hard it was to get Clinton to try self-deprecation.
George W. Bush definitely has a sense of humor, but it has a more physical side to it. He likes to mug for the camera or make silly faces when he messes up. It's not really my style, but I get the appeal. Al Franken once referred to Bush as the "third funniest guy in a frat." That sounds about right.
I was never sure that Bush Sr. or Carter were particularly funny people, although their speeches at the dedication of Clinton's presidential library were hilarious. Reagan had a sense of humor that was based on telling jokes that he'd learned years earlier. Sometimes this worked, sometimes it didn't.
I'm intrigued by Obama's sense of humor. His is the first in a while that actually appeals to me. If you caught his roast of Rahm Emanuel or his comments about DC weather yesterday or when he referred to himself as a "mutt," he's got this nice, dry, self-effacing wit, occassionally peppered with movie references. I guess I shouldn't be surprised that I feel like I can relate to this guy. He's the first president we've had in a long time who's an educated northern urban liberal. The last one was JFK.