We had heard several people recommend Freaks and Geeks to us, a canceled show about high school in the 80's, but unfortunately we never got around to watching it until recently. This show is awesome. It makes us cringe and celebrate the fact that due to straight F's in obedience school #1, we never made it to high school.
Sam Weir is a freshman in high school, and a total geek. He has two other friends who are also really geeky, loves Star Wars, has a huge crush on a cheerleader (who talks to him for unexplained reasons) ,and is repeatedly beaten up by a high school bully. Sam's older sister Lindsey is a high school brain who has decided to go the loser-loner-smoker route and become a total freak, oh and she also has a gigantic crush on Daniel, the head freak. Our favorite episode we've seen is where the geeks find out about drunk driving and alcohol poisoning and so decide to replace the beer at Lindsey's kegger with a keg of non-alcoholic beer they wheel home in a red wagon. The freaks get drunk anyways, the geeks blame the placebo effect.
Quick vote: This tv show is honest, frank, painful to watch, and hilarious. We highly recommend it!