The lists herein serve as more of a running reminder of what I've enjoyed so far (my memory is not very good). So obviously, it can't be a top 10 since the number may change as I add or delete entries as my mind wanders in its spiral descent. And I have many more than 10! Also, these lists are in no particular order since I can't really rank them. I've tried to include only ones that I would enjoy watching/reading again. For movies, multiple viewings are probably required to get the most out of them (at least, I've definitely needed to see them again to gain a better understanding).
Movies
Donnie Darko [2001] by Richard Kelly
A Clockwork Orange [1971] by Stanley Kubrick
Dr. Strangelove [1964] by Stanley Kubrick
Eyes Wide Shut [1999] by Stanley Kubrick
21 Grams [2003] by Alejandro Gonzalez Inarritu
Irreversible [2002] by Gaspar Noe (even though this movie is included, I would advise anyone to NOT WATCH IT!)
Sympathy for Mr. Vengeance [2002] by Chan-Wook Park
Kind-Hearted Ms. Geum-Ja (Sympathy for Lady Vengeance) [2005] by Chan-Wook Park
La Double Vie de Veronique [1991] by Krzysztof Kieslowski
Trois Couleurs: Rouge (Red) [1994] by Krzysztof Kieslowski
Mulholland Dr. [2001] by David Lynch
Before Sunrise [1995] & Before Sunset [2004] by Richard Linklater (these go together)
Alien [1979] by Ridley Scott
Chungking Express (2nd story) [1994] by Wong Kar-Wai
Fallen Angels (2nd story) [1995] by Wong Kar-Wai
Show Me Love (Fucking Amal) [1998] by Lukas Moodysson
Lilya 4-Ever [2002] by Lukas Moodysson
Exotica [1994] by Atom Egoyan
Children of Men [2006] by Alfonso Cuaron
South Park: Bigger Longer & Uncut [1999] by Trey Parker and Matt Stone
El Laberinto Del Fauno (Pan's Labyrinth) [2006] by Guillermo Del Toro
Trainspotting [1996] by Danny Boyle
The Godfather [1972] & The Godfather Part II [1974] by Francis Ford Coppola
The Rapture [1991] by Michael Tolkin
Tonari No Totoro (My Neighbor Totoro) [1988] by Hayao Miyazaki
Hotaru No Haka (Grave of the Fireflies) [1988] by Isao Takahata
A History of Violence [2005] by David Cronenberg
Inside Man [2006] by Spike Lee
Sin City [2005] by Frank Miller / Robert Rodriguez
Requiem for a Dream [2000] by Darren Aronofsky
Un Long Dimanche de Fiancailles (A Very Long Engagement) [2004] by Jean-Pierre Jeunet
Shimotsuma Monogatari (Kamikaze Girls) [2004] by Tetsuya Nakashima
Moulin Rouge! [2001] by Baz Luhrmann
Goyangileul Butaghae (Take Care of My Cat) [2001] by Jae-Eun Jeong
Little Miss Sunshine [2006] by Jonathan Dayton and Valerie Faris
Books
A Clockwork Orange by Anthony Burgess
The Stars My Destination by Alfred Bester
The Prestige by Christopher Priest
The Diamond Age by Neal Stephenson
The Fifth Head of Cerberus by Gene Wolfe
The Book of the New Sun by Gene Wolfe
The Wasp Factory by Iain Banks
Use of Weapons by Iain M. Banks
Feersum Endjinn by Iain M. Banks
The Song of the Dodo by David Quammen
Monster of God by David Quammen
Guns, Germs, and Steel by Jared Diamond
Collapse by Jared Diamond
Lolita by Vladimir Nabokov
China Mountain Zhang by Maureen F. McHugh
Foucault's Pendulum by Umberto Eco
The Russia House by John LeCarre
Jonathan Strange & Mr. Norrell by Susanna Clarke
Tehanu by Ursula K. LeGuin
The Weather Makers by Tim Flannery
City of Saints and Madmen by Jeff VanderMeer
Comics
The Sandman series by Neil Gaiman
The Miracleman series by Alan Moore / Neil Gaiman
Watchmen by Alan Moore
From Hell by Alan Moore
The Animal Man series by Grant Morrison
The Doom Patrol series by Grant Morrison