First my top 3...and I'm not sure if any of this has to do with liking Bukowski...let alone with his tastes...
The Lost Weekend (a good drinking movie, but read the book, there's alot they changed, like the ending).
Raging Bull (I know Buk was a fight fan, and as portraits go, this one of Lamotta is pretty damn good).
The Cooler (strange gambling film with William H. Macy and Maria Bello and a surprisingly good perfomance by Alec Baldwin).
Now the other thing...someone mentioned Leaving Las Vegas. I remember this came out just after I put down the bottle, and it had all the boys and girls in the church basements squirming. "Whatever you do," they said, "don't watch it alone...it'll make you drink." So of course, I waited until my wife (then fiancée) was out, and rented it.
Nick Cage really doesn't know anything about drinking. First off, if I were gona drink myself to death, I'd have a lot more fun with it. And if Elizabeth Shue were sucking me off, I'd seriously reconsider the whole death thing entirely. Was that rude? Sorry. Anyway, the film was a plodding load of crap, and no, it didn't make me drink.