Black and Grey Morality: The heroes are either essentially unaligned (three kids trying not to be bullied) or morally complex (a con artist who decides to do something good for once). The villain, however, is pretty unambiguously a bad guy.
Kids Are Cruel: The teens who hired Drillbit are constantly menaced by two bullies, one of whom is completely psychopathic. Not only do they perform the normal bully tactics, but at one point the bullies chase the protagonists with a car, apparently in an attempt to murder them for trying to report their behavior. What makes this even worse is that most of this is done in plain sight of the rest of the kids in school and they do absolutely nothing about it, at least until the protagonists finally grow some backbone and kick some bully ass.
No, You Go First: Drillbit almost confesses the truth about himself to Lisa, but before he does, she starts going on about how she usually dates absolute losers, and is so happy to be with a nice doctor.
Shout Out: When the bully attacks Drillbit, he gets punched in the ear and complains about it, similar to Tyler Durden in Fight Club. The boys even watch that scene later in the movie, though the exact line isn't shown.