The cast was filled with great young actors like Anthony Michael Hall who was in Hughes previous two films 16 Candles and The Breakfast Club, as well as co starring in National Lampoon's Vacation which Hughes wrote but did not direct. Kelly leBrock was an attractive, sexy model who was perfect in the role of Lisa. You also have some young kid by the name of Robert Downey Jr. who showed up as well as one of the "bad guys". But the actor who stole the show was Bill Paxton who has become quite the character actor as well, by his role as Chet, the brother of Wyatt played by Ilan Mitchell-Smith.
A quick synopsis of the film, two nerds during a wild weekend create a woman with their computer who they hope will do whatever they tell her to do, but the tables are turned as she tries to help them become accepted in who they are. I told you it was a crazy film. Bill Paxton as Chet is the abusive older brother of Wyatt who extorts money from his brother, gives him wedgies, beats him up, almost as an extreme older brother. And Paxton plays the biggest jerk in the world.
Paxton's Chet has a close shave military esqe haircut, acts like he is in the military, likes guns and hunting, and is a creepy abusive bully. When he catches Wyatt doing things he is not supposed to Chet extorts money from him so as not to tell their parents what he did. This partricular weekend their parents are going away for a weekend and leave Chet in charge. He decides to spend all day on Saturday hunting leaving Wyatt and Gary(Hall's character) to have their big party, and their time with Lisa. So Chet may not be in the film all that much, but when he is, you are drawn to him and you laugh at how big of a dick he is. From hurling insults at his brother, to walking around in a towel, to freaking out when he sees what his brother did to their house, then his sleaziness really comes through when he is hitting on Lisa, In the end though he gets his comeuppence in a huge way, and in a way that is perfect for Chet.
Paxton is able to create such a sleezeball, that no matter how over the top he gets, you think to yourself, yeah I can see someone being just like him. Paxton appears to be having a blast playing this role, because he can go way overboard and everything he does makes us laugh and hate him, but you kind of can't hate him because he is just so crazy insane. And he makes everyone laugh.