In o particular order(because I think, they'll get jealous of one another)

Fight Club. "You DO NOT TALK about Fight Club."
History Boys. If my memory serves me right, this was actually a play?
Requiem For A Dream. This one is very depressing, and quite disturbing, so be prepared if you do decide to watch this.
The Dangerous Lives of Altar Boys. This one too is quite sad.
Running with Scissors. Somewhat sad and funny.
Harry Potter 5 and 6. This is the beginning of the end *sad face*
Eternal Sunshine of the Spotless Mind. Jim Carrey actually delivered a good performance.
Click. Lighthearted and quite moving.
Little Miss Sunshine. Not your typical comedy movie.
Talladega Nights: The Ballad of Ricky Bobby. Will Ferrel is so funny!
Dan In Real Life. Light romantic-comedy-drama movie.
Evan Almighty. I thought Steve Carrel was waaay better thab Jim Carrey.
American History X. Two thumbs up for Edward Norton and Edward Furlong.
Wizard of Oz. I had nightmares when I was little because of the Tin man, LOL
The Man in the Iron Mask. If you're up for some grand adventure with the Musketeers :)
Sleepy Hollow. Tim Burton + Johnny Depp = how can you resist?
Edward's Scissorhands. Again, Tim Burton + Johnny Depp = how can you resist? :D
Sweeney Todd. Long live Tim Burton and Johnny Depp!
The Nightmare Before Christmas. Yes, I am a Burton fan.
The Wedding Singer. I fell in love with Adam Sandler in this movie.
The old Bond movies, not the ones with Pierce Brosnan and the Casino Royale guy. Ugh.
Back to the Future (all 3 of them). Marty McFly was my first love :)
Castaway. I don't know why, but this movie captivated me.
500 Days of Summer. My kind of bittersweet movie.

The only romantic movie that I would suggest you watch is Sassy Girl, it's a Korean film, it'll make you cry, laugh, laugh and cry. Hollywood rom-coms, for me, are basically the same. Similar plot, ending...

So yeah, I'll end my suggestions here, seems like i could go on forever. Have fun watching! :)