Jets
The beginning of the film shows Jack getting up from his nap in the desert and overhead there are planes flying through the sky. The imagery shows us that this cowboy is in opposition to a new world. He belongs to a time that has past.
Uncaged
When Jack is out the window to escape from prison we see the wire peeled halfway back. This is when Paul is telling him what real freedom is. The wire represents the complex nature of freedom between these two men as they have different personal definitions of, while at the same time understanding the others point of view.
Narrow Path
Miller shoots Jack and his horse through the door frame of a broken down home as they climb the ridge. This imagery tells us that their path has narrowed and there is very little room to maneuver as they are being chased by the police as they seek freedom.
Kickin' Up Dust
Jack is making his way up the ridge when he sees a dust trail left behind by an approaching vehicle. The shot is wide and you can barely make out what's coming, but the image allows us to understand, like Jack that he isn't free and clear just yet.