I just realized why “bad” is cool in middle/high school (35 years too late). It’s because, to be “bad,” you need to be socially and culturally sophisticated. If you are socioculturally inept, you don’t become “bad”; you end up becoming just “wrong.” Middle school is where kids first become aware of what constitutes “bad” in our culture.
What they are taught in elementary school is “right” versus “wrong.” The spectrum of right and wrong is more objective and, therefore, easier to learn. If you are academically smart enough, given enough examples, you will be able to figure it out on your own.
The spectrum of “good” and “bad” is more subjective, which makes it harder to master. There are no objective criteria by which we can determine someone is “bad.” It’s not up to you to decide who is “bad.” Even if you think you are “bad,” others may disagree. You need to have a decent grasp of what others consider “bad.” If you are unsuccessful at being “bad,” others would perceive you as “wrong” or “weird.”
But, you might ask, why focus on being “bad” instead of being “good”?
Being “good” is indeed harder than being “right.” Think of a kid who is always right about everything. It’s usually a geeky, academic kid who is socially inept. Being perceived as a “good” kid requires greater sociocultural awareness, but even greater awareness is needed to be “bad.” Why? Because you also have to know what you can get away with. There isn’t much risk in being “good,” so it requires much less sociocultural awareness. Think of a politically incorrect joke. To tell it effectively, you would have to be able to assess the risk accurately beforehand. If your assessment is wrong, you can get into serious trouble.
In this sense, becoming “bad” is a sign of growth, from being smart to becoming wise. Mastering “bad” is the ultimate sign of sociocultural intelligence.