True Grit (1969)

How the West was wiseass. A lot of the pleasure in watching this movie comes from the wry character of the dialogue—to be expected from a Charles Portis-penned script—particularly the sharp-tongued observations of John Wayne’s Rooster Cogburn and Kim Darby’s Maddie Ross. Their performances, along with solid support from Glen Campbell, raise these proceedings above the level of your average Western. Also enjoyable is seeing all those vistas of the then-still-unspoiled landscape—Colorado in this case—splashed across the screen. It’s not exactly a deep story, but overall the tale provides enough to interest the viewer. I don’t know about grit, per se, but this one certainly has solid, traditional movie-making on its side—and usually that’s enough. 

Cool Hand Luke

More a collection of memorable scenes than a good movie. The difficulty comes in trying to stitch those scenes together into something coherent and compelling. Luke's nihilism bleeds out any real end to the hero's means; it's tough to know why you're on his side beyond Newman's personal charm and presence. It could have been more, but ultimately this film is a "not quite."

Easy Rider

Actually not as good as the obscuring haze of time makes it out to be. But definitely worth a look as one of the defining works of its time. And more movies should have characters discussing the nature of life and society in them, as Jack Nicholson so memorably does here.