These are not in any particular order. (Though I have no problem with Brazil being on top, I’ll say that.) And this list is far from complete. Not sure exactly what the criteria for getting on it are. For now, let’s say I would have no reservations strongly recommending any of these movies to the right person in the right frame of mind.
 
Brazil
To Die For
Magnolia
Back to the Future(s)
The Frighteners
Twelve Monkeys
Tropic Thunder
Galaxy Quest
Being John Malkovich
The Incredibles
Stripes
Caddyshack
Matrix Trilogy
The Fisher King
War Games
The Cabin in the Woods
Sling Blade
Die Hard (& II & III)
Idiocracy
Primer
Bulworth
Fletch and Fletch Lives
Pump Up the Volume
Welcome to the Dollhouse
Jacob’s Ladder
The Player
Heathers
It’s a Mad, Mad, Mad, Mad World
Adaptation
Being John Malkovich
Lethal Weapon I & II
Joe Versus the Volcano
Memento
Hudson Hawk
Flirting with Disaster
O Brother, Where Art Thou?
Three Kings
Pleasantville
South Park: Bigger, Longer, and Uncut
Shaun of the Dead
What About Bob?
Old School
Ferris Bueller’s Day Off
Big Fish
Mystery Men
Minority Report
Ghostbusters
Harold & Kumar Go To White Castle
Rain Man
Stand By Me
The Untouchables
The Graduate
Dogma
Drop Dead Fred
Rushmore
Man on the Moon
Leaving Las Vegas
Raising Arizona
The Truman Show
Tucker and Dale Vs. Evil
Bonnie and Clyde
Butch Cassidy and the Sundance Kid
A Fish Called Wanda
Bottle Rocket
Mississippi Burning
Grosse Pointe Blank
The Fifth Element
Hudson Hawk
Looper
Stranger Than Fiction
Me and You and Everyone We Know
The Bourne Trilogy
Mars Attacks!
Pulp Fiction
Murderball
Spellbound (documentary)
Rocky
The Hitchhiker’s Guide to the Galaxy
Bubble Boy
Fargo
Hollywood Palms
This Film Has Not Yet Been Rated
Fuck (documentary)
The Aristocrats
Scotland, Pa.
Copland
Evolution
Cloudy With a Chance of Meatballs
Date Night
The Big Hit
John Dies at the End
The ‘Burbs
District 9
Conspiracy Theory
Bad Words
Attack the Block
Midnight Run
Paul
Bone Tomahawk
The A-Team
Kingsman: The Secret Service
Guardians of the Galaxy
Defendor
Kick-Ass
Super
The Matador
The Indiana Jones Quadrilogy (except maybe Temple of Doom)
Stretch
 
See also: TV I’ve Loved