These three movies are related, far more than I realized when I started watching them, as well as the one film, Inherant Vice, that I intended to bunch with the rest of these films. I initially put Jackie Brown in as an unrelated movie to revisit it as one of my favorite Tarantino movies to quickly realize that it fits in as a Private Investigator/ Los Angeles/ off beat/ mystery movie/ by a great director. Jackie Brown has a Bail Bondsman playing the role of a private investigator in a story of a heist like in Stanley Kubrick's film The Killing where a stash of money is stolen and many of the cohorts are killed off in the complexity of the heist... It also appears that the mask used by one of the characters and on the cover of the Criterion Collection blu-ray packaging is the same mask the Joker wears in the opening heist of The Dark Knight. After this viewing of Jackie Brown I feel more confident about placing it just behind the Kill Bill movies as my favorite Tarantino movies.
Watching all three of these movies together made a fun tour of Los Angeles, and all three films have us visit very strong and unique characters (including an unbilled Arnold Schwarz... Arnold Schwartzen... Arnold Strong playing a body guard trying to act tough by pulling his pants down and flexing in the background.) They're all stories about eclectic mixes of L.A. characters dropped into mysteries of either murder or bags of money. I would suggest watching any of the four films in a bunch, but strongly recommend Jackie Brown and The Big Lebowski over the other two which are a little slower. I do enjoy Inherent Vice as a film but it starts slow. It's not as "confusing" as many reviews pinned it, especially in the context of these other films where the viewer must be a private detective themself. The Long Goodbye is also a rather slow movie, it's a little meditative and sleepy at times, but for me it is a film that has been watchable and engrossing up until the final reveal throughout my life.
I saw The Long Goodbye the first time sometime in middle school and was not aware of the name of the movie, The Long Goodbye is not exactly catchy, but the idea of the movie, the coolness of Elliott Gould and his odd search for his cat (I probably shouldn't have seen it at that age due to his nudist neighbors) made it a memorable film for me. I saw it again in either high school or college with my friends, I remember it was one of them who rented it for us and early on I thought "I know this movie" and enjoyed it as I was reintroduced to the film. This viewing, well after college and law school the build up of the film and the strange renditions of the theme song as the only score for the film in different styles, the film was fun to see again, as this viewing I noticed Sterling Hayden, an actor I have enjoyed after college for his roles in the Kubrick films The Killing (again), and Dr. Strangelove.