Take the person out to the movie. See a comedy, 'The Hangover' or something. Get them out of their normal zone and head.

When my dad died with I was in college, some friends took me to see 'Pacific Cherry Private School' or something. It was a nice gesture and I've always remembered it.

Mommie Dearest

Into the Wild

barbara the barbarian.

the matrix

Titanic

Serious and considered answer with anecdotal evidence of effectiveness, the suggestion of which will be completely ignored by everyone, and especially by the OP since the thread is a moronic list thread even if some people are being serious:

The Fugitive

First of all it's very good and entertaining and fast-paced and absorbing, so that's all good for an escape.

Then at the end (spoilers I guess but I don't think tags are necessary) when he is absolved of the wrongful conviction for killing his wife, this sort of relieved/triumphant/sad/hopeful musical theme plays that to me says "well yea he's off the hook, but his wife is still dead so that kinda sucks, BUT life will go on".

I remember listening to parts of the soundtrack years ago when I was being a sad wuss about a girl, and it definitely gave me the feeling I described of a kind of acknowledgment of the sadness, but a hopeful "this too shall pass" feeling as well. It legitimately helped.

Also, Spanking the Monkey.

requiem for a dream

Cannibal holocaust

Salo

all tit ****ing vol. 8


eta- forget about Frankenpenis

Monty Python's Holy Grail
The Adventures of Baron von Munchausen
(both serious suggestions)