Of all the movies I've watched in my day, I can't think of one single character with a better attitude than Jon Bender. When you're younger, you kind of see Jon Bender as the burnout he is, and never really get into why he is the way he is. You may shed a tear or two when he shows Emilio his cigar burn from his dad, but the older you get, you start realizing that this is a very bright kid that just had a poor upbringing.
The thing about high school is these kids never really fit in. They're definitely not jocks, and they're too cool to be nerds. Naturally, they turn to things like drugs and alcohol and general non-conformity, although even non-conformists tend to form clicks be they hippies, vampires or whatever else goes on in high school. Bender assumes the role of a burnout and won't take any guff from an authority figure. I bet the teachers that treated him like a person never had any problem with him, but the ones … who craved power … (really excited to watch Lord of the Rings again) got the worst of him. Eight Saturday detentions in a row for Jon is proof of that.
Still despite the punishment, it's worth it. He gets the better of everyone in that movie and in the end hooks up with the prom queen. His sarcasm and belittling tone are the stuff I could only dream about when dealing with meatheads. The way he condescends Emilio Estevez that entire movie is how jocks should be spoken too. It's quite clear the only way Emilio can respond to the constant condescending is with stupid catch phrases only a jock would say and of course violence. Maybe there's some truth to the fact that Bender would waste him if they truly wrestled, but I guess John Hughes had to give the jocks a little something by letting Emilio win the short scuffle in the movie, though he definitely takes it back with the Emilio dancing scene. As someone who is not a fan of the meat-headed, MMA watching, shit sack kind, even I had to suspend disbelief as a jock acting with that much failure. Oh, that scene is terrible, I wouldn't wish it on anyone.