SFGate has a great article on how W. is That Guy:
In other words, he is indeed That Guy, like the best man at the wedding party, the one standing out in the center of the room, casually and cluelessly telling off-color jokes that offend everyone but which he thinks are gul-dang hilarious and, hell, if you're offended then you're just some gul-dang hippie liberal. Haw.
He is That Guy. The one who thinks he is everybody's bestest pal, the guy everyone wants to kick back with and have a few brewskies and chat about baseball and lawn fertilizer and Jesus. After all, isn't that what we all desire of the man who decides some of the most difficult, deadly, complicated issues on the planet? Isn't that slacked, frat-guy goofiness exactly what you want trying to broker peace in the Middle East and understand global warming and stem-cell research? Sure it is.
And when it comes to women (or rather, "wimmin"), well, it's all taken one step further. Or, rather, downward. It's like an awkward scene from "The Office," where Steve Carell's character Michael Scott, the smarmy manager everyone secretly loathes but who himself believes to be the funniest and most likable and naturally gifted guy in the room, walks up to one of his female employees and grabs a mango and cracks a grossly inappropriate joke about vaginas and laughs hard, slaps everyone on the back, and then takes a big, gross bite of the mango. What a kidder!
He does not, of course, realize no one else is laughing.