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...in no particular order...
Breakfast at Tiffany's - I just adore Audrey Hepburn, and she is perfect in this movie. I like this movie so much, I have the poster on my wall and I've dressed up as Holly Golightly for Halloween a couple times.
Braveheart - We've got Mel Gibson, stunning battle scenes, a little humor, two amazing love stories, and an Irishman who talks to God - what more could you want?
Office Space - "...I think you have my stapler...it's the red Swingline stapler...I'm going to burn the building down." Oh man, I just about cry everytime I see this movie. Long Live Milton!
American Beauty - this movie deserved every Oscar it got, and every one it didn't get. This is one of the few movies that uses special camera effects (i.e., the rose petals flying around, etc.) that don't annoy the crap out of me.
Monty Python and the Holy Grail - I know all the freakin' words. I used to have a guy roommate and he knew all the words too. Once we tried to show the movie to our third roommate and we annoyed the heck out of her by reciting along with the characters. (But she just sucked in general, I mean, who hasn't seen Monty Python????) There are just way too many damn good lines in this movie. "Your mother was a hamster and your father smelt of elderberries!" "She turned me into a newt! ... well, I got better." "Bring us a shrubbery!" "An African swallow or a European swallow?"
Honorable Mentions:
Star Wars - the original trilogy, not the offensively crappy Episodes 1 and 2. If Episode 3 sucks too it will break my heart.
Swingers - I liked this movie way before the whole world thought it was The Coolest Thing ever. One of my guy friends made me watch it, saying, "Watch this and you will understand how guys think." I loved the movie, loved it, loved it. Then a couple years later and every kid has the poster on their dorm wall.
Spaceballs - this is like Monty Python, so many fabulously funny lines. "May the Schwartz be with you!" Along that line, History of the World Part I was a darn fine movie too.
Elf - if you haven't seen this yet, get your butt to the theater. This is one of those laugh-so-hard-you-snort-Coke-out-your-nose movies. Will Farrell is a comedic genius.
I would list the original Matrix movie, but the 2nd one was so terrible that now I'm mad at the 1st one - that movie was just so darn good it really deserved better sequels. I'm not going to waste my money on the 3rd until it comes out on video.
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