Talking to a friend, I jokingly referred to this movie as the third part of the Patrick Wilson Impotence Trilogy, after Hard Candy and Watchmen. Barry Munday is named after the title character, an archetypical douchebag jerk. Wilson eschews any vestiges of his generally perceived persona: that of a reasonably well-educated, attractive nice guy.
(l. to r.) Shea Wigham and Patrick Wilson. Wilson looks like a chubby, sloppier Jeff Anderson from Clerks in Barry Munday.
Every night, Barry goes out to a bar, gets drunk, and relives his late teenage years on repeat. By day, he works in an insurance office for Lonnie Green (Billy Dee Williams). He spends every waking moment chasing tail, down to every stray thought. He makes one of his trademark bad choices and ends up in the hospital the next morning having lost both testicles. On top of that, he's served with a letter from the lawyer of one Ginger Farley (Judy Greer) saying that he fathered a child by her.
As for supporting cast, Jean Smart does a bang-up job as Barry's mom, Cybill Shepard and Malcolm McDowell pop up as Ginger's dress-alike parents, and Chloe Sevigny is very effective as Ginger's slutty, jealous sister. The standout for me, though, was Shea Wigham (Splinter) as Barry's douchebag best pal. He's not a household name, but Wigham does great work.
My wife mentioned before seeing the movie that there would probably be less problems in the world if there were some sort of Douchebag Castration Law on the books. Of course, then you get into the problem of interpretation possibly de-balling a bunch of non-douchebags, and then where would we be?
The big question tied to the movie's success is, whether he overcomes his jerkface tendencies or not, if Barry's journey is realistic in the face of the movie being a comedy (very broad in places). For me, it's as satisfying as The 40-Year-Old Virgin, and more believable than Knocked Up in many respects. Not every jerk like Barry will end up the way he does, but you believe the journey of this guy under these circumstances. The movie could make a studio a fair amount of cash pitching it as the comedy that takes down the King of the Douchebags.