I love Some Like It Hot but I could never just give you just five
Here are a few, I've narrowed it down to 25! This includes some recent favorites, these are films I could never have imagine not seeing:
La Strada
Star Wars; a new hope
Gone With the Wind
2001: A Space Odyssey
Hannah and Her Sisters
Amarcord
Some Like it Hot
Dazed and Confused
Manhattan
The Graduate
Broadway Danny Rose
Napoleon Dynamite
Ratatouille
Almost Famous
A Room With A View
I'm Not There
Willy Wonka and the Chocolate Factory ( 1971 )
The Rocky Horror Picture Show
Amadeus
Rushmore
E.T.
Raiders of the Lost Ark
The Sound of Music
Lord of the Flies ( 1963 Peter Brooks version )
The Wizard of Oz

Some Like It Hot . the greatest American movie in any genre.
Singin' in the Rain . the best musical
Godfather II the best sequel ever.
Ran the most beautiful film ever, (if a bit slow for some tastes).
Young Frankenstein very funny and strangely beautiful.
But you ARE Blanche and I AM.

Lord of the Rings (Trilogy)
Taxi Driver
A Clockwork Orange
2001: A Space Odyessey
Some Like It Hot
Gone With the Wind
One Flew Over the Cuckoo's Nest
The Bridge on the River Kwai
Spirited Away
all some of my favorite movies ever

In no particular order:
One Flew Over The Cuckoo's Nest
Die Hard 1
The Sting
Raiders of the lost Ark
The Usual Suspects
What about top 5 comedies:
Office Space
Ace Ventura
Dumb and Dumber
Life of Brian
Old School

have you seen any movies that don't contain morgan freeman or al pacino?

1. Shawshank redemption
2. Godfather/Godfather part II
3. Casino
4. Goodfellas
5. Million dollar baby

ooh, i love chinatown. i forgot about that one. choosing a top 5 is such a HARD thing to do.

1. Casablanca
2. Vertigo
3. Chinatown
4. Dog Day Afternoon
5. Taxi Driver

harrymovie
that's probably the only list in the whole bunch that i give any respect to.
as far as some of the semi-respectable lists, you need to see a LOT more movies.
so, what's my fave 5, you might ask?. man, it's sure easier to rip on other peoples choices than to put out your own. it's hard to even remember all the movies one has seen. but off the top of my head something like this, in no order:

1. Nowhere In Africa
2. Solaris (Solyaris the 1972 original)
3. Oldboy
4. Ran
5. Office Space
6. Spirited Away
7. The Lord of the Rings Trilogy
8. The Godfather Trilogy
9. All About My Mother
10. Pulp Fiction
11. Bridge on The River Kwai
12. The Decalogue
13. Deliver Us From Evil
14. Spring, Summer, Fall, Winter and Spring
15. A Clockwork Orange
16. Cool Hand Luke
17. The Treasure of the Sierra Madre
18. Memento
19. Irreversible
20. Alien
    damn, that's 20. and i'm sure i could do 50 without much more thought.

1. Cinema Paradiso (1982)
2. The Kid (1921)
3. Persona (1966)
4. The Godfather (1972)
5. Fanny & Alexander (1982)

1. Cititzen Kane
2. Casablanca
3. The Godfather
4. Gone with the Wind
5. Singin in the Rain

Star Wars Episodes IV-VI
2001: A Space Odyssey
Schindler's List
A Clockwork Orange
Taxi Driver
The Apartment
Anchorman: The Legend Of Ron Burgundy
Platoon
All That Jazz
Gandhi
Jurassic Park
Gladiator
Citizen Kane
Life is Beautiful
the Green Mile
Dead Poets Society
I am a jedi, like my father before me

1.The shawshank redemption
2.Back to the future
3.Saving Private Ryan
4.Forrest Gump
5.Some like it hot

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If you want better answers why don't you post this question on a general IMDB forum? YOure getting generation close to deaths opinion by posting it here.

I replied you about the greatest movies of all time.
Here i mention the greatest comedies ;

1. Some Like It Hot
2. The Gold Rush
3. Sherlock Jr.
4. To Be Or Not To Be
5. His Girl Friday & Bringing Up The Baby (At the same level i think)
6. Annie Hall
7. Modern Times
8. Duck Soup
9. Zelig
   10)The General
   The greatest black comedy of all time : Dr. Strangelove

Wow, tough ask.
I couldn't prioritise them, but I might say

• Casablanca
• Godfather/Godfather II
• Gone With The Wind
• Lord of the Rings
• Seven Samurai
• The General (Buster Keaton)
• 2001: A Space Odyssey
  oh, was I supposed to stop?! (If I'd kept going, I would have probably added Ben Hur and Wizard of OZ and hmmm, left the 10th spot free for What Is Yet To Come, I think.)
  Yeah, I've taken liberties, but in my defence I consider the first two Godfather movies as twin spawns of the one genius, and LotR as effectively one very looooong movie spun from the one sustained fever dream. It wouldn't be fair to split them up.
  You
  might
  very well think that. I couldn't possibly comment.

On the wrong board once again. What is it doing on the Some Like It Hot board?
Thats not biased AT ALL!
Stop Radioactivity

1. Modern Times
2. Some Like It Hot
3. Rear Window
4. A Man For All Seasons
5. Fargo

1. A Clockwork Orange
2. Blow Up
3. American Beauty
4. Some Like It Hot
5. Rebel Without A cause

I agree fully.
My Top 25 Films
http://landofcinema.forumcircle.com/viewtopic.php?t=565

FW Murnau. What a stunning, creepy film it is.

5. Nosferatu
   Whick one? Murnau or Herzog version?
   My Top 25 Films
   http://landofcinema.forumcircle.com/viewtopic.php?t=565