What was the name of this John Hughes-esk movie?

OK, this movie was made something in the early 2000s, I think; it had a decent-sized cast, about 8 regulars. It was basically what would happen to John Hughes characters when they hit their late twenties to early thirties: alcoholics and druggies. The premise was a woman and her fiancee were trying to sell her parent's home, and for shits and giggles she invites a bunch of her old high school friends for a party at the house. From there it's stories about the characters, from who they slept with last to who slept with who first; there's a scene in a hot-tub, someone gets arrested for drunk/high driving, two characters have a deep moment at a football field. The main character's younger brother sells vintage action figures out've his basement to make extra money while his sister thinks he's selling drugs. It's gonna bother me until I remember the title. Music was a big deal, there were constant arguments about "the best song ever.", at one point over a game of pool.