Actually the idea of a gangster who wants to be educated by that unemployed writer is quite brilliant. It has great irony which could make a fine comedy, a good action or a nice noir about the difference between the 2 worlds of them both. The movie cleverly tried to make a strange romance out of it, with some thrill, yet with a character's analysis that really says a lot about the personality of the contemporary cultured.
I love it all together; the simple direction, the effective acting, the bluesy music. It was all about the fallen world of (Jake Bridges), and how this gifted man just loses it when he confines himself faraway beyond the factual humans and things, to become that isolated literate who cut all the *bridges*, and had nothing to present nor to tell. But now the story to till about, or to report about to be precise, is the life of that gangster who's shown as more sincere, honest and ethical! It's that marvelous situation of one conscious brain but inanimate, and one twisted muscle but so active. So, of course, the world will be for the second man, and when that second also searches for goodness, then love too will be for him!
It's (Casablanca - 1942) again. But with the famous sentimental exile as a modern cultured who's less idealistic than the gangster. Therefore, the end here was ingenious with (Frankie McGregor/Michael Wincott) and (Melissa/Diane Lane) being together free under the sun - as he deserves her better - and (Jake Bridges/William Petersen) is in jail, metaphorically his own jail of misgivings, writing at last as he finally lived an experience to write about, which came from his late interaction with real people. But again, he was writing about them from the same idiot perspective: "It's funny. People you don't expect to love are the ones you never forget!". Look at his ever dull point of view "People you don't expect to love..", he still treats according to previous concept as they're all lower than him, and he sadly still somehow denies his love for them "you never forget..", even if they're fun to remember, and painful to miss.
So what's the motif of that (Rick Blaine)'s ugly new copy?! It's the human journey into the big world just to discover oneself. Thus, the self of that gallant authentic gangster wanted such a good place in real life, so he won love. And that swindler learned loiterer, who wants a book, money or even the same love, perhaps will get everything except love. Why is that?! Maybe because he was loving himself all along, seeing no one except himself. Or maybe because he is the perfect exile cultured who is meaner, and less strong-willed, than the ex-criminal. So what a satire that this movie presents against (Bridges), and his likes, as the real criminal who's too detained and barren to learn or feel anything true and lasting.