I found Cool Hand Luke boring and mildly depressing.
I think the Eastwood Dirty Harry movies would work for your son, but I haven’t seen one for quite a while so I might be wrong.
(I exclude The Dead Pool from that recommendation)
I saw the movie for the first time in 20 years last month. I think the reason critics considered it so groundbreaking at the time is because it was one of the first American movies that portrayed the law as the villian and the lawbreakers as heroes. Remember the scene where Clyde walks into the bank and asks the man at the teller window if that’s his money or the banks? When the man replies it’s his, Clyde lets him keep the money. In contrast the law has no problem taking the land people worked their entire lives (the scence where B&C run into the man looking at his forclosed home). Everything the law does seems duplicitous, whether it’s doing night ambushes or the final setup.
Now the movie isn’t nearly as shocking but it’s still teriffic. (Well except for Blanche; how Estelle Winwood won an Oscar for screaming the entire film stuns me.) The scene where Bonnie visits her mother is the best; she knows her choices in life have doomed her. These aren’t two stick figures just shooting people–they are real humans and their choices have consequences.
I’m surprised there’s so little love for Bonnie and Clyde in this thread. I first saw as a high schooler in the late '90s, and I was absolutely transfixed. Saw it again a few years ago and still loved it. My sister saw it and called me to say how impressed she was.
3rd suggestion: Boys N The Hood. I’m sure 20 years ago the title was a lot less lame sounding, but it’s a great movie with great acting. He will probably get a kick out of recognizing still famous actors as they were 20 years ago.
I wasted a few hours watching the latest version of B&C. The main thing I got from it was that they (apparently) had a white hot lust for eachother-they were always making love.
Many years ago, I read a book about B&C-the author claimed that , far from being a sex addict, Clyde was likely impotent! Bonnie came along for the excitement.
Was Clyde actually homosexual?
The Wannsea Conference is one of the scariest - though it is only in the idea of the movie - otherwise it is a bunch of guys meeting in a mansion in Berlin [to casually discuss killing off 12 million assorted people]
The Bridge is one of the saddest - a bunch of boys effectively sentenced to death - Home Guard Hitlers Youth defending a bridge against adult US soldiers. AThey didn’t stand a chance.
Here’s a bigger-budget, award-winning movie about the Wannsee Conference, starring Kenneth Branagh and Stanley Tucci. Chillingly good: Conspiracy (2001 film) - Wikipedia
The main not-so-great thing about Bonnie and Clyde was that as gangsters they were way overrated, so it’s only through massive fictionalization that they are interesting or sympathetic characters.
They were cheap hoods who mostly robbed things like markets and gas stations (relatively few bank robberies, and then for little money). Bonnie was rarely involved in actual shooting and mostly hung around and occasionally wrote bad poetry. They did get involved in some cold-blooded murders, but got relatively little publicity outside of their stomping grounds in Texas and adjacent states. Compared to Dillinger, Baby Face Nelson, Karpis etc. they were small-timers.
The most ironic thing in re: reputations of the 30s crooks, is that all of these guys were low rent, even Dillinger and his crew, compared to Harvey Bailey and his usual cohorts. Yet, nobody even remembers Bailey, his autobio was poorly written, and not even a good ghostwriter got involved in it. Shows what a good movie will do for you!