I have a massive movie collection, but there are only a few that stand the real test of time that can be watched, and are watched, again and again with new levels of enjoyment. For films I require a high level of acting, story, believably, human interaction, or just plain fun, etc.
Here are some of those films and if you've never seen them you'd be wise to check these out. I would rate these films all 5-star with high re-watchability and/or multi-layers of dynamic story and acting.
Holidays:
Planes Trains and Automobiles (Steve Martin, John Candy)
It's a Wonderful Life (Jimmy Stewart)
White Christmas (Bing Crosby)
A Christmas Story
Comedy:
The Three Amigos (Martin, Chase, Short)
Dumb and Dumber (Jim Carey)
Naked Gun 1 and 2 1/2
Old School
Anchorman
Dodgeball
The Big Lebowski
Office Space
Action/SCI FI:
Mad Max and The Road Warrior (Mel Gibson)
Alien and Aliens (stellar cast)
Terminator (Arnold)
Raiders of the Lost Ark and Indiana Jones/Lost Cruisade (I & III)
Predator (Arnold)
Heat (Pacino and Deniro)
Ronin (Deniro)
Blade Runner (Ford)
Star Wars IV and V (and only IV and V)
Die Hard (Bruce Willis)
The Thing (Kurt Russel)
Conan (Arnold)
Gladiator (Russel Crow)
The Abyss
War:
Band of Brothers (10 part series)
Saving Private Ryan (Tom Hanks and strong cast)
Platoon (Charlie Sheen)
Full Metal Jacket (R Lee Ermery)
Black Hawk Down
Drama:
A Few Good Men (Cruise, Moore, Nicholson)
Collateral (Tom Cruise)
Pulp Fiction
Resevoir Dogs
Rocky (all)
Usual Suspects
Miracle (Kurt Russell)
Horror:
The Shining (Jack Nicholson)
Signs (Mel Gibson)
Halloween
28 Days later and 28 Weeks later
Jaws
TV Series (on Netflix)
Frasier
Cheers
The Killing (Seattle based detective story)
How I met your mother (surprisingly funny and great)
The Walking Dead