The 20 Most Mind-Bending Movies of All Time

Movies, like other art forms, have the ability to overshadow their purpose when it comes to entertainment. In fact, many do just that, and as a result, we are often left with an array of unimaginable, mind-boggling questions. Every once in a while filmmakers like to challenge their audience's psyche by creating their films in a way that allows us to examine the philosophical ideas of human identity, science, consciousness etc...

There are plenty of movies that have been made over the years that are written, acted and directed in such a way that their audiences are inevitably left with thoughts and feelings that are deep and at times emotional, ones that have a lasting effect.

Here is our list of 20 of the most thought-provoking movies, some of which have confusing plots, and open endings that will have you conjuring up many interpretations, ones that can very well change the entire meaning of what you've just witnessed on screen.

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20 Vanilla Sky (2001)

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Tom Cruise plays David Aames, a man lost in his own dreams. But then again, his life basically is a dream; he's young, successful and handsome. However, after a car accident with a jilted ex lover, his dreams soon turn into nightmares, as dreams often do, and shortly after his life becomes entwined with chaos.

Vanilla Sky is a deep, dark and psychological drama about dreams and reality, and essentially "what might have been." The meaning of the movie is hidden well behind the car crash, but if you pay close attention, there are many references and clues throughout the film that give it more depth.

19 Donnie Darko (2001)

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The main character, Donnie Darko (Jake Gyllenhaal) suffers from sleep walking and delusions which include visions of a large bunny. The bunny named Frank manipulates Darko into committing different crimes and also informs Darko that the world is coming to an end, leaving him with intense dread and he eventually begins questioning if the events in his life are actually real or illusions.

After your first viewing, it's very possible that you will want to watch the movie a second time or maybe even a third, and you may very well need to, as Donnie Darko is one of those rare movies in which every scene has an underlying meaning and is therefore open to several explanations.

18 Oldboy (2003)

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Oldboy follows Dae-Su who is kidnapped, finds himself locked up in a make-shift prison and is confined there for 15 years. After enduring years of isolation and suicide attempts, he wakes up from a gas-induced coma on top of a tower box where he was originally captured. With no explanation as to why this has happened to him, he then proceeds to try and find the answers to all of his unanswered questions.

The film is twisted with a plot that unravels into a dark outcome. The viewers really have to delve deep in thought and think outside of the box when trying to piece together the events that transpire, leading up to a jaw-dropping surprise ending.

17 Identity (2003)

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Unusual circumstances bring eleven people, strangers to each other outside of their respective "groups", together and they end up stranded in an uninhabited Nevada motel on a stormy night. Soon bodies start turning up and things are not what they seem. One by one they begin to get killed... But for what reason and by whom?

Identity is a psychological thriller at its best, with a story that has a number of twists and turns, and keeps you guessing until the end.

16 The Number 23 (2007)

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The movie follows Walter (Jim Carrey), and the events that lead up to his life becoming filled with paranoia. Walter convinces himself after reading a novel that the number 23 is haunting him and he soon begins to align similarities between the main character in the novel and his own life.

The Number 23 is a well-written and thought-provoking story full of paranoia, obsession and redemption, with an ending that will blow your mind.

15 Dead Ringers  (1988)

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David Cronenberg's Dead Ringers, is about twins Elliot and Beverly Mantle, both gynecologists. Being extremely close the two share everything and very few people can tell them apart; an arrangement they both use to their advantage, until Beverly falls for a patient and soon discovers there are things he doesn't want to share with Elliot.Dead Ringers is not a traditional film, it's actually quite complex, and at times can be very hard to look at it. It's an unsettling psychological drama, definitely not the type of movie to watch on a date, but rather one that requires some thought and a craving for understanding human nature.

14 Cube (1997)

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Cube is a sci-fi thriller about 6 strangers; a cop, a math whiz, a doctor, a building designer an escape master, and a disabled man, who are involuntarily placed in a dangerous and endless maze, trying to find their way out.

This is one movie that explores human nature and our instinctive urges for survival vs our humanitarianism. Cube could almost be categorized as a disturbing film, not because of its graphic content, but rather due to the thoughts that it can plant in its audience.

13 Moon (2009)

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Moon tells the story of Sam Bell, the only resident of an automated lunar mining base whose sole task is to extract Helium-3 from lunar rocks that need to be shipped back to Earth.

After an isolated three-year posting, Sam's mind becomes unbalanced, leaving the audience to wonder if the events that are unraveling are actually happening, or simply a result of his now diluted mind. Moon really makes you thoroughly think about all that's happened in the film as it touches on issues like corporate greed, scientific ethics, compassion and human identity.

12 The Believer (2001)

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Inspired by real events, The Believer reveals the story of a young Jewish man who struggles with his beliefs. Ryan Gosling plays Danny, whose ideas about his religion lead him into a world of hatred and denial. Flashbacks shown through the movie allow us to see how he struggled with his early teachings of Judaism and his lack of understanding, which eventually leads him to become a race–hating skinhead.

It's a film about self-loathing in a world without hope, one that needs to be watched more than once. It's thought-provoking due to the fact that the film only provides questions, never any real answers, leaving the viewers to discover their own interpretations of The Believer.

11 Detachment (2011)

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Detachment revolves around a cynic substitute teacher (played by Adrien Brody) who arrives at a dangerous school where he ends up connecting to some of the students and teachers on his latest assignment. The school is brutal, and is full of students that are prone to bullying each other, even their teachers.

This dark film, is one that everyone can relate to. It demonstrates the cynicism, solidarity and despair that can sometimes come into our lives, and confronts both psychological and physical tragedies. Detachment is a movie that everyone should see at least once, not necessarily because of the direction it takes but rather the underlying message it sends.

10 Mulholland Dr. (2001)

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A car crash leaves a woman an amnesiac, which brings on a catalyst of a hopeful search for clues and delivers shocking answers in a twisting adventure beyond dreams and reality.

9 9.The Machinist (2004)

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The Machinist is about an industrial worker (Christian Bale), who suffers from insomnia and hasn't slept in a year. This condition causes him to lose weight, and distorts his perception of reality.

How can a man not sleep for an entire year, wasting away and keep his sanity? That is just one of the questions the viewer will be asking themselves as they watch this film unfold.

8 1984 (1984)

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1984 takes place after The Atomic War and the world is now divided into three states in a futuristic society. Winston Smith is a bureaucrat, rewriting history in one of the departments, but one day he commits the crime of falling in love. Through this rebellion, he and his lover try to escape the clutches of big brother who hears and sees everything, but nobody can really escape, can they?

The film is an adaptation of  George Orwell's timeless novel 1984.  Like the novel, this movie is brilliantly made and will have you asking yourself many philosophical questions about the future, humanity, love and power. It's a film that casts harsh judgements on the state of the world, especially when it comes to the watchful eye of big brother-operated governments.

7 A Beautiful Mind (2001)

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A Beautiful Mind is a biopic of John Forbes Nash Jr., a math genius who was able to solve problems that have perplexed some of the greatest minds. The film follows the story of how he overcame years of torment, battling schizophrenia and went on to win the Nobel Prize.

The psychology of this movie is intriguing on many levels, not to mention the mathematical philosophies that were accurately described throughout the film.

6 The Matrix (1999)

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The story of The Matrix revolves around a man who lives two lives. By day he's a typical computer programmer and by night, a hacker with the alias Neo. He ends up crossing paths with underground freedom fighters who help him understand that the reality he thinks he knows is actually more complex than he could ever imagine.

The Matrix is an ideal example of symbolism through action and philosophy. It supplies enough thought-provoking content for the intellectual to analyze and discuss, that college professors actually show this movie in their philosophy classes to generate deep discussion among their students.

5 Fight Club (1999)

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Edward Norton plays an average guy existing in a dead-end life who suffers from insomnia and is yearning for some kind of change in his life. He stumbles across soap maker, Tyler Durden (played by Brad Pitt) and they end up building an underground fight club that emerges into something much more...

Fight Club exposes the endless emptiness of modern existence, and explores solutions to the fabricated reality that invades modern life. It's been criticized over the years for its violence, but any reviewer claiming this film is promoting violence has missed the entire point of Fight Club. It merits at least a second viewing if not more, just to take it all in, especially if you haven't read the book.

4 Memento (2000)

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Memento tells the story of Leonard Shelby, a man who lost his short-term memory due to a vicious assault in which his wife was raped and murdered. Despite his short-term memory loss he creates an odd system in hopes of finding his wife's murderer.

Memento is an extremely intelligent brain teaser, one that will have you guessing from beginning to end. The story is told in reverse so you never know more than the main character. Every scene keeps you on the edge of your seat as you try to theorize what is going on and put the pieces together backwards, just as Shelby does.

3 2001: A Space Odyssey (1968)

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2001: A Space Odyssey questions politics, science, technology, evolution, the concept of "knowledge" itself, and what they all actually mean. The significance for humanity is mind-blowing, and the very fact that the aliens are never shown only adds to the colossal mystery. Is it impossible for humans to see them? Are they purposely not showing themselves? It really makes you think about the limits of how great mankind could eventually become.

2 Inception (2010)

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Leonardo DiCaprio plays a world class criminal who enlists the help of a team of sleep experts in order for him to work his way into people's subconscious and steal their most prized possessions. Now on his last assignment, he is faced with a massive dilemma when he discovers certain people have been trained to prevent their thoughts from being taken.

Inception is an exceptionally complex film, one that examines the depth of the subconscious mind. The best part about the movie is that you may very well feel that you need to watch it again to be able to completely absorb the experience. Chances are that it may take more than that to understand Inception in its entirety.

1 Jacob's Ladder (1990)

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A haunted Vietnam war veteran tries to unravel his past while suffering from an extreme form of dissociation. His days are filled with flashbacks of his first marriage, his dead son and his time in Vietnam. In order to discover his past, he must break down and understand reality from his own dreams and perceptions.

When watching the movie, the viewer experiences a powerful force that can weaken your natural ability to remain in control of your thoughts. In a sense, it's like being in a trance, a hypnotic state that restricts you from thinking, or believing in anything apart from the intense feelings that Jacob's Ladder triggers. As far as psychological movies go, this one reigns supreme.

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