Love this film. Much like Top Gun, this was watched by young me until my VHS copy fell apart. With the girlfriend the other day we decided to give it a spin, my first time in over ten years, and it still holds up. It suffers from a bad case of '80s, but the actors are all charming and the violence is top notch.
Emilio Estevez is especially engaging. He's an actor that has laid low recently, but here he's magnetic. He manages to make Billy a sympathetic character while lending him a degree of self-destruction and selfishness that adds nuance. It's even worse in the sequel, but he's willing to get his friends killed to accomplish his rather nebulous goal (I'm not sure if it's to the movie's benefit or not that Billy and John Tunstall aren't allowed much time to bond, but Billy takes the man's death worse than the rest), to avenge Tunstall's death. This goal, however, comes across as a rather blatant excuse for Billy to win fame and glory, and also to kill. We're given very little backstory for the character, but Estevez balances his bloodlust and need for attention well with a funny charm (and laugh!), and it's convincing that these young men would follow this ambitious man to their deaths with the promise of "pals" for life.
The rest of the cast, especially Keifer Sutherland, is great. All very funny but ruthless when need be. These were, after all, criminals. The only problem is that the movie, at times, ventures into portraying them like a rock (or boy) band. You know, the smart one, the pretty one, the ethnic one. It doesn't help that silly guitar riffs keep butting into the otherwise traditional western score.
I'll also give much credit to the pacing and sense of geography. This is a movie that balances action and character development well, taking moments to contemplate gallows humor and the big questions of life and death. These young men are barely old enough to have experienced life but they deal death casually. I especially like Doc, an academic type that is implied to have had a hard background and yet can't escape from the "whirlwind" that is Billy. He tries to act like he's not, but he's a killer like all the rest of them. They're all bad men, but there's an inevitability to their story. The action, meanwhile, is always clearly shot and I love how the bullet impacts are shown and the Regulators themselves don't come across as invincible as they're constantly being wounded (especially Dirty Steve's gangreney arm wound, ew).
Great supporting cast all around. Terry O'Quinn, Jack Palance, there's a sense of world building to everyone on display, like you can buy these characters having active lives offscreen.
An old favorite of mine.
