Sean Penn was (and still is) the ultimate movie bad boy. His appearance, his demeanour, everything about him exudes 'chip on the shoulder'. It could be argued that Penn so perfectly suits such roles that he's really not acting at all. He's just putting his true personality onto film.
Bad Boys is Sean Penn's film. He plays Mick O'Brien, a kid who's in deep trouble. He steals purses from old ladies, bashes pedestrians on the head, plans armed robberies, and mows down innocent kids if they get in the way of his escape. This guy is one nasty dude. For reasons we never quite understand, he's the object of goody-two-shoes J.C. Walenski's (Ally Sheedy) affections. Her taste in men is equalled by her judgement, as demonstrated by wandering home alone through the mean streets of Chicago after dark.
Mick finally gets sent to a youth detention facility. Here he encounters the usual prison-yard horrors, and a system that rewards the prison's top thug in much the same way as a pride of lions or other collection of wild beasts. What better incentive to take a bag full of soft drink cans and cave in the head of the current head bad boys?
Mick struggles with life on the inside, until his love for J.C. finally brings out signs of humanity. Penn delivers a strong performance, although it’s too bad we never learn more about how he got off track.
The rest of the cast isn't as successful, ranging from prison stereotypes to apparent refugees from Welcome Back Kotter, including obviously over-aged 'kid' actors such as Clancy Brown, who was 24 when the film was released. Penn was 23.
Bad Boys makes an earnest effort to show the grimy side of 'bad boy' life, but it falls short due to implausible situations and mediocre acting, with the notable exception of Penn.