Motel room alcoholic movie?

This has been bothering my partner for years and I think I’ve also seen it? Movie takes place primarily at a crappy roadside motel featuring an alcoholic man slowly descending deeper into his addiction.

He maybe wears suits throughout? Guy hangs out with a lot of sex workers and someone (maybe him) dies.

Real dark, very indie. From the 90s/2000s? But by a film bro famous director. Not David Lynch or Christopher Nolan or David Fincher, but does have some of the same vibes vaguely. One of the director’s earlier movies for sure