Three of my favorite movies he was in are Easy Rider (1969), Five Easy Pieces (1970) and The Last Detail (1973). He has a pretty small part in Easy Rider but that movie was a generational milestone. If you've never seen it Peter Fonda and Dennis Hopper are on a cross country motorcycle trip intending to sell some drugs (hidden in the gas tank of one of the motorcycles) in Mexico. They stop by New Orleans and drop acid with some wild women. It all made sense at the time. Very cool when I was 15 years old, not sure what it would look like today. It's got a great old rock and roll soundtrack.
He plays a Navy lifer chief in Last Detail taking a young kid to the brig. The movie has a classic scene where a bartender threatens to call the shore patrol and Jack gets excited and slams his gun down on the bar and says - "I am the mother f..ing... shore patrol." You'd have to watch it to get the effect.
5 Easy Pieces is just a cool movie. Jack's a worker in the oilfields who is sort of displaced. There's some great scenes where he plays a piano in the back of a pickup truck driving across a bridge and ordering a sandwich in a cafe where he tells the waitress in his sardonic slow voice that she can take the chicken and...
I don't want to ruin it for you.
Easy Rider: Music From The Soundtrack (1969 Film)
____________________________
Based on the reviews I've read and the trailers The Departed (2006) directed by Martin Scorsese - with Jack Nicholson, Leonardo DiCaprio, Matt Damon, Mark Wahlberg, Martin Sheen, and Alec Baldwin looks good. It gets a very high 8.6 rating from viewers on IMDB.