Hmm while some of these may not be hardly known (some are just outright classics) they may have been fogotten...well at least by Steve
Few picks out of my collection....
State of Grace (1990)
http://www.imdb.com/title/tt0100685/7.1/10
Tagline: A family ripped apart by violence. A love corrupted by betrayal. A friendship stained by blood.
Plot Outline: Terry Noonan returns home to New Yorks Hells Kitchen after a ten year absence. He soon hooks up with childhood pal Jackie who is involved in the Irish mob run by his brother Frankie. Terry also rekindles an old flame with Jackies sister Kathleen. Soon, however, Terry is torn between his loyalty to his friends and his loyalties to others.
Director: Phil Joanou
Starring: Sean Penn, Ed Harris, Gary Oldman
21 Grams (2003)
http://www.imdb.com/title/tt0315733/7.9/10
Tagline: Difference between dead and life
Plot Outline: This is the story of three gentle persons: Paul Rivers (Penn) an ailing mathematician lovelessly married to an English emigré (Gainsbourg), Christina Peck, an upper-middle-class suburban housewife, happily married and mother of two little girls, and Jack Jordan (Del Toro), an ex-convict who has found in his Christian faith the strength to raise a family. They will be brought together by a terrible accident that will change their lives. By the final frame, none of them will be the same as they will learn harsh truths about love, faith, courage, desire and guilt, and how chance can change our worlds irretrievably, forever.
Director: Alejandro González Iñárritu
Starring: Sean Penn, Naomi Watts, Benicio Del Toro
Memento (2000)
http://www.imdb.com/title/tt0209144/8.6/10 (Top 250: #27)
Tagline: Some memories are best forgotten
Plot outline: A man, suffering from short-term memory loss, uses notes and tattoos to hunt for the man he thinks killed his wife.
Director: Christopher Nolan
Starring: Guy Pearce, Carrie-Anne Moss, Teddy Gammell
At this point Id like to say you need to watch all of Christopher Nolans movies, they are all excellent. 3 out of 6 of his movies are in the IMDB top 250. Quick list (and if you can watch them in this order, you may enjoy the experience more of seeing him develop his craft):
Following (1998 )
http://www.imdb.com/title/tt0154506/7.6/10
Memento as mentioned before (2000)
Insomnia (2002)
http://www.imdb.com/title/tt0278504/7.2/10 (Al Pacino, Robbin Williams)
Batman Begins (2005)
http://www.imdb.com/title/tt0372784/8.3/10 (Top 250: #95)
The Prestige (2006) as youve already mentioned
http://www.imdb.com/title/tt0482571/8.4/`0 (Top 250: #90)
I know some of the ones Ive just mentioned are hardly hard to find, but just in case Steve isnt aware he needs to catch up on his Nolan viewing
Oldboy (2003)
http://us.imdb.com/title/tt0364569/8.3/10 (Top 250: #117)
Tagline: 15 years of imprisonment, five days of vengeance
Plot Outline: An average man is kidnapped and imprisoned in a shabby cell for 15 years without explanation. He then is released, equipped with money, a cellphone and expensive clothes. As he strives to explain his imprisonment and get his reveng, he soon finds out that not only his kidnapper has still plans for him, but that those plans will serve as the even worse finale to 15 years of imprisonment.
Director: Chan-wook Park
Starring: Min-sik Choi, Woo-jin Lee
If you like Fear & Loathing you may be interested in Darren Aronokskys work, although it tends to be much darker/grittier...
Pi (1998 )
http://www.imdb.com/title/tt0138704/7.5/10
Tagline: faith in chaos
Plot Outline: A paranoid mathematician searches for a key number that will unlock the universal patterns found in nature.
Starring: Sean Gullette
Requiem for a Dream ( 2000)
http://www.imdb.com/title/tt0180093/8.3/10 (Top 250: #63)
Plot Outline: The hopes and dreams of four ambitious people are shattered when their drug addictions begin spiraling out of control.
Starring: Ellen Burstyn, Jared Leto, Jennifer Connelly, Marlon Wayans
And you may remember Sam mentioning The Fountain (2006) recently:
http://www.imdb.com/title/tt0414993/Things to Do in Denver When Youre Dead (1995)
http://www.imdb.com/title/tt0114660/6.5/10
Tagline: They can die quickly. They can die slowly. But they must die!
Plot Outline: Five different criminals face imminent death after botching a job quite badly.
Director: Gary Fleder
Starring: Andy Garcia, Christopher Walken, Steve Buscemi
The Insider (1999)
http://www.imdb.com/title/tt0140352/7.9/10
Tagline: Warning: Exposing the Truth May Be Hazardous
Plot Outline: A research chemist comes under personal and professional attack when he decides to appear in a "60 Minutes" expose on Big Tobacco.
Director: Michael Mann
Starring: Al Pacino, Russell Crowe
Wildcard classic 80s comedy.....
Trading Places (1983)
http://www.imdb.com/title/tt0086465/7.3/10
Tagline: Theyre not just getting rich... Theyre getting even.
Plot Outline: A snobbish investor and a wily street con artist find their positions reversed as part of a bet by two callous millionaires.
Director: John Landis
Starring: Dan Aykroyd, Eddie Murphy
Twelve Monkeys (1995)
http://www.imdb.com/title/tt0114746/8.0/10 (Top 250: #194)
Tagline: The future is history
Plot Outline: In a future world devastated by disease, a convict is sent back in time to gather information about the man-made virus that wiped out most of the human population on the planet.
Director: Terry Gilliam
Starring: Bruce Willis, Madeleine Stowe
The following from Terry Gilliam is also very good:
Brazil (1985)
http://www.imdb.com/title/tt0088846/8.0/10
Tagline: Tagline: Its only a state of mind.
Plot Outline: A bureaucrat in a retro-future world tries to correct an administrative error and himself becomes an enemy of the state.
Starring: Robert De Niro, Bob Hoskins, Michael Palin
And finally...
Very Bad Things (1995)
http://www.imdb.com/title/tt0124198/5.8/10
Tagline: For boys who should know better...
Plot Outline: A prostitute is killed during a bachelor party and the attendees turn on each other as the wedding approaches.
Director: Peter Berg
Starring: Jon Favreau, Leland Orser, Cameron Diaz, Christian Slater, Jeremy Piven
Ive never understood Very Bad Things low rating, I think its one of the best black comedies out there, so Id suggest screw the rating and watch it because I loved it.
See what you think of those... Ive focused on Drame, Crime, Sci Fi, Black Comedies, but if you like those then Ill recommend some others out the 500 remain I have