I Can't Sleep

Movies whose main characters are insomniacs or were proper insomnia is relevant.

Other movies related to dreams an sleep-related themes are included in my other list Dreamology.

Randomly ordered, ongoing, list
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1.
Cashback (2006)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
After a painful breakup, Ben develops insomnia. To kill time, he starts working the late night shift at the local supermarket, where his artistic imagination runs wild. (102 mins.)
Director: Sean Ellis
 
2.
Insomnia (2002)
    1 2 3 4 5 6 7 8 9 10 7.2/10 X  
Two Los Angeles homicide detectives are dispatched to a northern town where the sun doesn't set to investigate the methodical murder of a local teen. (118 mins.)
 
3.
The Machinist (2004)
    1 2 3 4 5 6 7 8 9 10 7.7/10 X  
An industrial worker who hasn't slept in a year begins to doubt his own sanity. (101 mins.)
Director: Brad Anderson
 
4.
Chasing Sleep (2000)
    1 2 3 4 5 6 7 8 9 10 6.4/10 X  
A college professor wakes up to find his wife has not returned home, then struggles to understand her disappearance. (104 mins.)
Director: Michael Walker
 
5.
The Haunting (1999)
    1 2 3 4 5 6 7 8 9 10 4.9/10 X  
When Eleanor, Theo, and Luke decide to take part in a sleep study at a huge mansion they get more than they bargained for when Dr. Marrow tells them of the house's ghostly past. (113 mins.)
Director: Jan de Bont
 
6.
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
 
7.
Lost in Translation (2003)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
A faded movie star and a neglected young woman form an unlikely bond after crossing paths in Tokyo. (101 mins.)
Director: Sofia Coppola
 
8.
Taxi Driver (1976)
    1 2 3 4 5 6 7 8 9 10 8.3/10 X  
A mentally unstable Vietnam War veteran works as a night-time taxi driver in New York City where the perceived decadence and sleaze feeds his urge for violent action, attempting to save a preadolescent prostitute in the process. (113 mins.)
Director: Martin Scorsese
 
9.
Memento (2000)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
A man juggles searching for his wife's murderer and keeping his short-term memory loss from being an obstacle. (113 mins.)
 
10.
Sleepless in Seattle (1993)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A recently widowed man's son calls a radio talk-show in an attempt to find his father a partner. (105 mins.)
Director: Nora Ephron
 
11.
The Insomniac (2009)
    1 2 3 4 5 6 7 8 9 10 -/10 X  
Ali is a workaholic writer who does not believe in rest. His sleepless efforts to complete his latest work of fiction are slowly forcing him to lose his mind. On one fateful night, his imagination gets the better of him. (88 mins.)
Director: Madhav Mathur
 
12.
No Rest for the Brave (2003)
    1 2 3 4 5 6 7 8 9 10 5.9/10 X  
(104 mins.)
Director: Alain Guiraudie
 
13.
Lucid (2005)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A Canadian therapist has one last chance to keep his own personal life afloat by avoiding a job transfer to Gimli and working to help three patients suffering from extreme post-traumatic stress disorder. (92 mins.)
Director: Sean Garrity
 
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15.
They Shoot Horses, Don't They? (1969)
    1 2 3 4 5 6 7 8 9 10 7.9/10 X  
The lives of a disparate group of contestants intertwine in an inhumanely grueling dance marathon. (129 mins.)
Director: Sydney Pollack
 
16.
Hands on a Hard Body: The Documentary (1997 Documentary)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Twenty-four contestants compete in an endurance/sleep deprivation contest in order to win a brand new Nissan Hardbody truck... (98 mins.)
Director: S.R. Bindler
 
17.
Carnivàle (2003 TV Series)
Episode: Insomnia (2003)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Ben tries to stave off the torments of his dreams by staying awake, but the lack of sleep is taking its toll... (55 mins.)
 
18.
Sleepwalker (2007 Short Film)
    1 2 3 4 5 6 7 8 9 10 -/10 X  
An insomniac journeys the streets of Cambridge, Massachusetts; meeting some interesting characters along the way. (5 mins.)
Director: Dave O'Halloran
 
19.
So You Think You Can't Sleep (1953 Short Film)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
Average working man Joe McDoakes tries desperate measures to cure his chronic insomnia. (10 mins.)
Director: Richard Bare
 
20.
An Insomniac's Nightmare (2003 Short Film)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A night in the life of a young chronic insomniac suffering from tormented delusions and frightening visions of his past. (31 mins.)
Director: Tess Nanavati
 
21.
Penn & Teller: Bullshit! (2003 TV Series)
Episode: Sleep, Inc (2008)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
Penn and Teller look at the pseudoscience that has built up around peoples need to get a good nights sleep. (30 mins.)
 
22.
Goodnight Nobody (2010 Documentary)
    1 2 3 4 5 6 7 8 9 10 7.1/10 X  
The mysterious world of the sleepless. Four insomniacs from around the world invite us to spend a night with them. While the rest of the world sleeps, they're awake. (76 mins.)
 
23.
Caffeine (1999)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Caffeine addict Mitchell hasn't slept for three days. On a late night search for coffee he reluctantly takes over security duties at a 24-hour supermarket. (55 mins.)
Director: Paul Dowie
 
24.
Tuba Atlantic (2010 Short Film)
    1 2 3 4 5 6 7 8 9 10 7.5/10 X  
Everybody is going to die one day. Oskar (70) is going to die in 6 days. He is now ready to forgive his brother for a disagreement years ago... (25 mins.)
Director: Hallvar Witzø
 
25.
Sleepwalk with Me (2012)
    1 2 3 4 5 6 7 8 9 10 6.8/10 X  
A burgeoning stand-up comedian struggles with the stress of a stalled career, a stale relationship, and the wild spurts of severe sleepwalking he is desperate to ignore. (81 mins.)
 
26.
Interstellar (2014)
    1 2 3 4 5 6 7 8 9 10 8.6/10 X  
A team of explorers travel through a wormhole in space in an attempt to ensure humanity's survival. (169 mins.)