Withnail & I (UK 1987)

In Withnail & I, two young out-of-work actors (Richard E. Grant and Paul McGann) are freezing in their apartment. They go out to the country for a few days and freeze in a cottage owned by Withnail's uncle. They go there in a battered Jaguar Mk 2. Even if you don't care what your car looks like, make sure it has fully functioning windshield wipers and headlights.

Set in 1969. Based on an unpublished novel by writer-director Bruce Robinson based loosely on his life in London at that time. Withnail's uncle Monty (Richard Griffiths) coming on to Paul McGann was based on Robinson's experience acting in the movie Romeo & Juliet when Zeffirelli took an inordinate interest in him. 

Usually, I look at movies like this and think the characters' lives wouldn't be so bad if they would just cheer up, but their lives looked awful, freezing in an apartment, McGann being friends with an alcoholic and living with him as a roommate.  

To paraphrase the late Alexander Cockburn, friendship is often a question of how much you're willing to put up with and for how long.

Not quite the same genre as Midnight Cowboy or Of Mice and Men where you have two impoverished people who have no one but each other, but neither one is of any help to anyone. These two have theatrical agents and one has a wealthy uncle he turns to.

I guess I should mention that it's a comedy. 

Available on The Criterion and on Max.