So cliche, but they genuinely are my top 5, so:
Pulp Fiction
Shawshank Redemption
Fight Club
2001
The Shining
The first 3 are indeed great films and cult classics but only the Shawshank Redeption would make my Top 5. That's another for the OP to try, but not before bedtime, it's quite long so start early or prepare for a late night!!!!
On that note The Green Mile is also a definite must watch.
I remember enjoying True Romance years ago too with Christian Slater and Patricia Arquette. Great film and story line. Was never a blockbuster but a great film nonetheless!
You're nothing until you know every word of Quadrophenia
Seen the 3 you mentiond, and if I remember right, I had my first love with the girl in true romance. Great film as are the other 2.
green mile very sad I actually had a lump in my throat.
One of the sadest film I remember watching was terminator 2, nearly cried everytime lol
Snatch.
Layer Cake.
The Business.
Goodbye Charlie Bright.
Legally Blonde 2
Miss Congeniality 2
Sex & The City 2
I Still, STILL Bloody Well Know Exactly What You Did Last Autumn 2
I was only 13 I think when T2 came out and my mum dressed me up smart to go the cinema to watch it as it was a 15 certificate!
If you're in to a sad films occasionally then I can recommend The Bucket List with Morgan Freeman and Jack Nicholson, very warming but also hard hitting and emotional about very real life issues. I rented it from Blockbusters (remember them!) a few years ago with the missus and got a Pizza Hut take away to watch it with. at the end I was literally blubbing so much I couldn't breathe, just like when you're a kid and you REALLY hurt yourself for the first time. Perhaps it just because it was based on things close to my own life I don't know I don't think I could watch it without proper crying again. I think everyone who has any kind of emotional feelings should watch it at least once.
The Descendants is also a very good film that is sad but enjoyable at the same time and also ticks all the boxes for the stereotypical "chick flick" for the ladies.
I also think lockstock should be there well funny . Can everybody stop getting shotBit of a theme there, but wot no Sexy Beast? The Business is a big guilty pleasure of mine, great soundtrack as well.