The Newton Boys (1998) review

Uvalde-born Willis Newton (Matthew McConaughey) convinces his younger brothers Jess (Ethan Hawke), Dock (Vincent D'Onofrio) and Joe (Skeet Ulrich) to go along with him and his partner Brent Glass (Dwight Yoakam) robbing banks - for the most part, they have an alarming amount of success, Willis falls in love with single mother Louise (Julianna Margulies), a daytime heist in Toronto gets botched, they try going "legit" in the oil business (but fail) ... and then attempt to steal millions from a train.  While I didn't watch this when it first came out in the late '90s, in retrospect it's easy to see what would draw the innately empathetic Linklater to the subject: the Newtons are charming dreamers who recognize the system is rigged, don't want to pick cotton for a living and purposely avoid hurting anyone in the process ... and are even apologetic about it.  The bright-eyed cast helps compensate for the slightly roundabout manner in which the story is told ... and the fact that several of the "boys" made it to their eighties is pretty sweet.  The real Dock was arrested in 1968 (at 77!) for trying to rob a bank in Rowena, Texas: old habits die hard.