As far as Dennis Hopper, he's Babalugats, a character seen through much of the film. If you do an image search for Dennis Hopper Cool Hand Luke, you'll find lots of stills from the film. If you do a search for Dennis Hopper Cool Hand Luke YouTube, you'll find various video clips from the film with him. For example, he's in this clip of the car wash scene starting at 1:13.
http://www.youtube.com/watch?v=0MSWBmjzwFA
I don't remember it being mentioned why Dragline is at the prison camp.
I don't remember the context of the "few days left" line you're referring to, but if it's when they make him repeatedly dig a hole and fill it in until he breaks, it wouldn't be referring to him having only a few days left on his sentence because he's had a significant amount of time added for his escape attempts.
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