My top 20 of the past 20 years

In no particular order...
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1.
Fight Club (1999)
    1 2 3 4 5 6 7 8 9 10 8.8/10 X  
An insomniac office worker, looking for a way to change his life, crosses paths with a devil-may-care soap maker, forming an underground fight club that evolves into something much, much more. (139 mins.)
Director: David Fincher
“ The title turned me away at first, but the movie won me over in seconds. ” - RonnieRocket
 
2.
Mulholland Dr. (2001)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
After a car wreck on the winding Mulholland Drive renders a woman amnesiac, she and a perky Hollywood-hopeful search for clues and answers across Los Angeles in a twisting venture beyond dreams and reality. (147 mins.)
Director: David Lynch
“ Easily one of Naomi Watts' finest performances. How was she snubbed at the Oscars? ” - RonnieRocket
 
3.
The Life Aquatic with Steve Zissou (2004)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
With a plan to exact revenge on a mythical shark that killed his partner, oceanographer Steve Zissou rallies a crew that includes his estranged wife, a journalist, and a man who may or may not be his son. (119 mins.)
Director: Wes Anderson
“ This movie always gets better with repeat viewings. ” - RonnieRocket
 
4.
The Big Lebowski (1998)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
"The Dude" Lebowski, mistaken for a millionaire Lebowski, seeks restitution for his ruined rug and enlists his bowling buddies to help get it. (117 mins.)
Director: Joel Coen
“ If you don't like this movie, we can't be friends. ” - RonnieRocket
 
5.
Funny Games (2007)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
Two psychopathic young men take a family hostage in their cabin. (111 mins.)
Director: Michael Haneke
“ A devilish eye poke at casual blood lust. ” - RonnieRocket
 
6.
Shortbus (2006)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
A group of New Yorkers caught up in their romantic-sexual milieu converge at an underground salon infamous for its blend of art, music, politics, and carnality. (101 mins.)
“ An uplifting film with a climax. ;) ” - RonnieRocket
 
7.
Paris Is Burning (1990 Documentary)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A chronicle of New York's drag scene in the 1980s, focusing on balls, voguing and the ambitions and dreams of those who gave the era its warmth and vitality. (71 mins.)
“ A study on regality in the slums of NY. ” - RonnieRocket
 
8.
Fear and Loathing in Las Vegas (1998)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
An oddball journalist and his psychopathic lawyer travel to Las Vegas for a series of psychedelic escapades. (118 mins.)
Director: Terry Gilliam
“ Watching this movie was like being on drugs. I remember feeling disembodied after watching this. ” - RonnieRocket
 
9.
Crumb (1994 Documentary)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
An intimate portrait of the controversial cartoonist and his traumatized family. (119 mins.)
Director: Terry Zwigoff
“ The first documentary I ever loved. While it shows Crumb to often times be a bit of a creep, I never watch this film without wanting to draw soon after. ” - RonnieRocket
 
10.
Ed Wood (1994)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
An ambitious but troubled movie director tries his best to fulfill his dream, despite his lack of support. (127 mins.)
Director: Tim Burton
“ A bitter sweet movie in that it is perfect, yet reminds us that Tim Burton can make quality work, but makes Planet of the Apes instead. It's also just incredibly funny. ” - RonnieRocket
 
11.
The Idiots (1998)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
The group of people gather at the house in Copenhagen suburb to break all the limitations and to bring out the "inner idiot" in themselves. (117 mins.)
“ The ending has a surprising sense of warmth I found to be incredibly inspiring. This film got my brain going in so many directions. Easily the best in the Dogma 95 films, even if von Trier did break a couple of his own obstructions. ” - RonnieRocket
 
12.
Moon (2009)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
Astronaut Sam Bell has a quintessentially personal encounter toward the end of his three-year stint on the Moon, where he, working alongside his computer, GERTY, sends back to Earth parcels of a resource that has helped diminish our planet's power problems. (97 mins.)
Director: Duncan Jones
“ A clever sci-fi that reminded me more of Solaris and 2001 than anything in years. ” - RonnieRocket
 
13.
Dead Man (1995)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
On the run after murdering a man, accountant William Blake encounters a strange North American man named Nobody who prepares him for his journey into the spiritual world. (121 mins.)
Director: Jim Jarmusch
“ A sparse western that has a hollow creepiness to it, as if Death itself were the director. ” - RonnieRocket
 
14.
Happiness (1998)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
The lives of several individuals intertwine as they go about their lives in their own unique ways, engaging in acts society as a whole might find disturbing in a desperate search for human connection. (134 mins.)
Director: Todd Solondz
“ Worst film to watch with your father. Ever. ” - RonnieRocket
 
15.
Dazed and Confused (1993)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
The adventures of high school and junior high students on the last day of school in May 1976. (102 mins.)
“ I don't think I need to argue the merits of this film. A stoner film that transcends stoner films- brilliant. ” - RonnieRocket
 
16.
Trainspotting (1996)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
Renton, deeply immersed in the Edinburgh drug scene, tries to clean up and get out, despite the allure of the drugs and influence of friends. (94 mins.)
Director: Danny Boyle
“ The bedsheet breakfast scene may have been squick, but the rest of the film is hardly diminished by it. Dare I say it affords it? ” - RonnieRocket
 
17.
Mean Girls (2004)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Cady Heron is a hit with The Plastics, the A-list girl clique at her new school, until she makes the mistake of falling for Aaron Samuels, the ex-boyfriend of alpha Plastic Regina George. (97 mins.)
Director: Mark Waters
“ A black comedy cleverly disguised as a teeny-bopper flick. I had no desire to see this movie and it has actually become a guilty pleasure of mine. ” - RonnieRocket
 
18.
The Dark Knight (2008)
    1 2 3 4 5 6 7 8 9 10 9.0/10 X  
When the menace known as the Joker wreaks havoc and chaos on the people of Gotham, the Dark Knight must come to terms with one of the greatest psychological tests of his ability to fight injustice. (152 mins.)
“ By jove, I do believe Heath Ledger handed Jack Nicholson his ass! ” - RonnieRocket
 
19.
Dark Days (2000 Documentary)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A cinematic portrait of the homeless population who live permanently in the underground tunnels of New York City. (82 mins.)
Director: Marc Singer
“ Incredibly sad portrayal of a unique group of homeless people living just inches away from passing trains. The documentary does a good job allowing the story to tell itself. ” - RonnieRocket
 
20.
Twin Peaks: Fire Walk with Me (1992)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
A young FBI agent disappears while investigating a murder miles from Twin Peaks that may be related to the future murder of Laura Palmer; the last week of the life of Laura Palmer is chronicled. (135 mins.)
Director: David Lynch
“ The film does virtually nothing to wrap up the television show. However, when you consider the subject matter, the complete change in tone from the quirkiness of the show to dark madness is tasteful and gripping. ” - RonnieRocket