Oh lordy, there are a spate of movies that I watch repeatedly. While the list is seemingly endless I do have a "top-ten" that changes order from time to time and a "top-five" that doesn't change order because they're just simply too damn great to move down the list.
Off the top of my head: (note if it starts going alphabetical it's because I'm getting it off my list of movies)
Ben Hur (1959 Charlton Heston)
Shawshank Redemption
Seven Samurai
Ran
Star Wars (original three ...ok, ok, Ep. 4, 5 & 6 )
Braveheart
Meet John Doe
Maltese Falcon
Casablanca
City Lights (Charlie Chaplin... this is a
MUST SEE for anyone who hasn't!!)
Das Boot (The Boat)
True Grit
Enter The Dragon
Hero
Crouching Tiger Hidden Dragon
Cyrano de Bergerac 1950 (JoseÂ’ Ferrer -- his acting with this is fantastic!)
Day The Earth Stood Still
Duck Soup (Marx Brothers ... another
MUST SEE!)
A Fish Called Wanda (Don't ever,
ever call me stupid!)
The Good, The Bad, & The Ugly
Highlander
The Hunchback Of Norte Dame 1939 (Laughton)
Jeremiah Johnson
KellyÂ’s Heroes
King Kong 1933 original
Les Miserables 1935 (March/Laughton)
Oliver! 1968 (one of the best musicals)
The Princess Bride
The Rock
Rocky
Rocky II
Sahara 1943 (This is a great war movie with Bogart)
Sixteen Candles (What's a Hoppening Hot Stuff?)
Terminator
Tommy Boy
Harry Potter Series
Usual Suspects
Pulp Fiction
Kill Bill (1 & 2)
The War Of The Worlds 1953
WhatÂ’s Up Doc? (A great comedy one of the last Screwball Comedies)
whew... too many I know (but not all of my repeats) .... but yeah I do watch these again and again

If you haven't seen any of these ... by all means rent them and watch 'em...