In no particular order: 
1) Fight Club (1999)
2) The Machinist (2004)
3) Inception (2010)
4) Exam (2009)
5) Black Swan (2010)
6) Donnie Darko (2001)
7) Vanilla Sky (2001)
8) Shutter Island (2010)
9) Hard Candy (2005)
10) Magnolia (1999)
11) Spider (2002)
12) Memento (2000)
13) The Usual Suspects (1995)
14) The Prestige (2006)
15) Jacob’s Ladder (1990)
16) V for Vendetta (2006)
17) Mulholland Drive (2001)
18) Identity (2003)
19) A Beautiful Mind (2001)
20) Cube (1997)
Spotlight on Film 
Disagree with 18, 1, and 8. I wouldn’t call any of them compplicated, and not really intelligent either.
However, the rest of your list is fantastic. Like and/or love most of them!
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A well-made list, for sure. I love these kinds of films… and I’d say out of these, Hard Candy and Memento are my favorites. I’m still in awe that the general public understood Inception. I suppose that’s just how well-made it was, though.
Getting my hands on Muholland Drive soon to finally see it, since people keep telling me I’d adore it.
Nice post! 🙂
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Thanks! ) I think you are right about ‘Inception’. Only on my second watch I started to comprehend what was actually going on in the film. But Nolan is Nolan. And, do see ‘Mulholland Drive’. It was the last film I’ve seen from my list. It took me so long to actually see it because I was VERY skeptical about its alleged ‘complexity’ and ‘cleverness’. But, that was in the past, and I love it now. I am going to review the film soon.
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If your arielcts are always this helpful, “I’ll be back.”
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This is a really outstanding list. A lot of great titles. There are some that I still must see, including The Machinist, Jacob’s Ladder, and Exam, among others.
Mulholland Drive reaches a point about 100 minutes in where everything is flipped and nothing makes sense. However, after some thinking, it’s easier to piece things together. One of Lynch’s very best. I wrote about it a while ago, and you actually commented on it (thanks!).
As an aside, have you ever seen Primal Fear? It’s not nearly as complex or deep as some of the titles on this list, but it has a great twist ending that makes you reconsider the whole film, and Edward Norton’s performance (in his first role!) is superb.
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This is a great list – The only change I would make is to add ‘films made in the last 20 years’ in the title. Only because there are so many incredible, deep complicated films made since the 1930’s, that your list would be ten times this size if you were to incorporate them all. Missing for me here would be more cerebral films that are not complicated to grasp but deal intelligently with complicated issues: Death and the Maiden, or 6 Degrees of Separation, Talk to her or even Irreversible, The Piano Teacher or Hidden. Oh – I also think Naked is one of the most important / complicated films made in the last 20-30 years.
Great post – inspiring stuff! Thanks so much!
(just realized you could compile this list forever)
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Yes (sigh) it’s true – so many of the best films ever made are only watched by film students these days. (boo)
Your list got me thinking though. Really – we’re so fortunate that there are so many incredible films available that get us thinking and questioning our reality. There are a few on your list I haven’t seen, and some I want to see again – HOW good is Memento?
Thanks again for a great post.
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Nice list – have you seen many other David Lynch films? I really enjoyed ‘Lost Highway’, which is probably on a par with ‘Mulholland Drive’ in terms of its complexity. Perhaps even more difficult to understand is ‘Inland Empire’, although I really enjoyed the style of direction, and some of the scenes are incredibly well done.
Another Brad Anderson film I found interesting was ‘Session 9’, which also offers a chilling portrayal of mental illness (although I think I preferred ‘The Machinist’).
Great post 🙂
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“Exam” has been sitting on my Netflix Instant queue for a while. I’m going to bump it up. I try not to read anything about it to preserve that element of surprise.
The only other movie I haven’t seen on the list is “Spider.” I’ll check that out, too. 🙂
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this is great
thanks
this is the movie list i want
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Great list. Glad to see “Jacob’s Ladder” on there; I still remember it vividly, even though I haven’t seen it in 20 years. One other I’d suggest is “Frailty.” It’s on the lines of “Identity” but I think it’s even more creepy.
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I agree most of the list are well made and interesting films. But do you watch foreign-language films. From recent years I would argue that ‘Taxi Teheran’, ‘Winter Sleep’ and ‘Our Little Sister’ are at least equally fine.
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Well, obviously this list was compiled in December 2011, now I need a new one just to put all the more recent thought-provoking stuff into that. Although Winter Sleep failed to move me, I am yet to watch the other two you mentioned.Thanks for your suggestions.
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Vanilla Sky is absolutely one of my fav movies, but every time I mention it, people look at me like I’m crazy!
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Well, “Vanilla Sky” may appear slightly controversial because it is a remake of a much-loved Spanish film “Abre Los Ojos” (1997), also with Penelope Cruz. But, the concept in both films is pretty fascinating and thought-provoking. I have no idea why people may not like it.
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Great post 🙂 Glad to see somebody else online that I know who loves Shutter Island as much as I do. Anyway, keep up the great work as always 🙂
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