I just watched Superbad for the first time, and while I thought it was decent, and pretty funny in the final analysis, it was hard work to get through. I struggle with awkward and embarrassing movies, especially of the Judd Apatow formula: completely charmless, pathetic male protagonists that bumble through the movie making complete asses out of themselves. Or, at least, a movie like that has to be leavened with a great deal of silliness for me to be able to enjoy it (like the police sub-plot in Superbad). I thought Talladega Nights struck a good balance in this regard.
I'm not sure exactly why it is I have such a reaction to such movies, but it's an extraordinarily powerful one. It's a visceral physical discomfort. If the movie is sufficiently awkward, I literally cannot watch. I had to turn off Old School. The idea behind that kind of humor seems to be a kind of release from fear—watching someone else humiliate himself as a celebration of freedom from such humiliation (at that moment, anyway). My taste leans more toward the absurd (like Monty Python), where the jokes have no victim; or satire, where the victims genuinely deserve to be humiliated. Perhaps as a somewhat awkward person myself I too easily sympathize with Apatow's protagonists. Watching such movies, I am certainly reminded of my own numerous abject failures.
But it's more than that, I suspect. Though I'm no social savant, I am not quite fit to star in an Apatow film. High school was not a particularly hard time for me. I was never bullied, had plenty of friends, and reasonable success with girls. It might just be too much sympathy for the underdog. Whatever the reason, it's got a strong grip.