Best in Film - Dark Comedy

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1.
Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
An insane general triggers a path to nuclear holocaust that a war room full of politicians and generals frantically tries to stop. (95 mins.)
Director: Stanley Kubrick
 
2.
Observe and Report (2009)
    1 2 3 4 5 6 7 8 9 10 5.8/10 X  
Bi-polar mall security guard Ronnie Barnhardt is called into action to stop a flasher from turning shopper's paradise into his personal peep show. But when Barnhardt can't bring the culprit to justice, a surly police detective is recruited to close the case. (86 mins.)
Director: Jody Hill
 
3.
Harold and Maude (1971)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
Young, rich, and obsessed with death, Harold finds himself changed forever when he meets lively septuagenarian Maude at a funeral. (91 mins.)
Director: Hal Ashby
 
4.
Arsenic and Old Lace (1944)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A drama critic learns on his wedding day that his beloved maiden aunts are homicidal maniacs, and that insanity runs in his family. (118 mins.)
Director: Frank Capra
 
5.
The Ladykillers (1955)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Five diverse oddball criminal types planning a bank robbery rent rooms on a cul-de-sac from an octogenarian widow under the pretext that they are classical musicians. (91 mins.)
 
6.
Clue (1985)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
Six guests are invited to a strange house and must cooperate with the staff to solve a murder mystery. (94 mins.)
Director: Jonathan Lynn
 
7.
Thank You for Smoking (2005)
    1 2 3 4 5 6 7 8 9 10 7.6/10 X  
Satirical comedy follows the machinations of Big Tobacco's chief spokesman, Nick Naylor, who spins on behalf of cigarettes while trying to remain a role model for his twelve-year-old son. (92 mins.)
Director: Jason Reitman
 
8.
Fargo (1996)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
Jerry Lundegaard's inept crime falls apart due to his and his henchmen's bungling and the persistent police work of the quite pregnant Marge Gunderson. (98 mins.)
Director: Joel Coen
 
9.
The Truman Show (1998)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
An insurance salesman/adjuster discovers his entire life is actually a television show. (103 mins.)
Director: Peter Weir
 
10.
The Great Dictator (1940)
    1 2 3 4 5 6 7 8 9 10 8.5/10 X  
Dictator Adenoid Hynkel tries to expand his empire while a poor Jewish barber tries to avoid persecution from Hynkel's regime. (125 mins.)
Director: Charles Chaplin
 
11.
The Hangover (2009)
    1 2 3 4 5 6 7 8 9 10 7.8/10 X  
Three buddies wake up from a bachelor party in Las Vegas, with no memory of the previous night and the bachelor missing. They make their way around the city in order to find their friend before his wedding. (100 mins.)
Director: Todd Phillips
“ (Shared with "The Hangover Part II") ” - JackRabbitRutherford
 
12.
Tropic Thunder (2008)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
Through a series of freak occurrences, a group of actors shooting a big-budget war movie are forced to become the soldiers they are portraying. (107 mins.)
Director: Ben Stiller
 
13.
Kind Hearts and Coronets (1949)
    1 2 3 4 5 6 7 8 9 10 8.1/10 X  
A distant poor relative of the Duke of D'Ascoyne plots to inherit the title by murdering the eight other heirs who stand ahead of him in the line of succession. (106 mins.)
Director: Robert Hamer
 
14.
Pineapple Express (2008)
    1 2 3 4 5 6 7 8 9 10 7.0/10 X  
A process server and his marijuana dealer wind up on the run from hitmen and a corrupt police officer after he witnesses his dealer's boss murder a competitor while trying to serve papers on him. (111 mins.)
 
15.
Monsieur Verdoux (1947)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A suave but cynical man supports his family by marrying and murdering rich women for their money, but the job has some occupational hazards. (124 mins.)
Director: Charles Chaplin
 
16.
Death Becomes Her (1992)
    1 2 3 4 5 6 7 8 9 10 6.5/10 X  
When a woman learns of an immortality treatment, she sees it as a way to outdo her long-time rival. (104 mins.)
Director: Robert Zemeckis
 
17.
Mary and Max (2009)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
A tale of friendship between two unlikely pen pals: Mary, a lonely, eight-year-old girl living in the suburbs of Melbourne, and Max, a forty-four-year old, severely obese man living in New York. (92 mins.)
Director: Adam Elliot
 
18.
The Big Lebowski (1998)
    1 2 3 4 5 6 7 8 9 10 8.2/10 X  
"The Dude" Lebowski, mistaken for a millionaire Lebowski, seeks restitution for his ruined rug and enlists his bowling buddies to help get it. (117 mins.)
Director: Joel Coen
 
19.
Murder by Death (1976)
    1 2 3 4 5 6 7 8 9 10 7.4/10 X  
Five famous literary detective characters and their sidekicks are invited to a bizarre mansion to solve an even stranger mystery. (94 mins.)
Director: Robert Moore
 
20.
The Hospital (1971)
    1 2 3 4 5 6 7 8 9 10 7.3/10 X  
An over-burdened doctor struggles to find meaning in his life while a murderer stalks the halls of his hospital. (103 mins.)
Director: Arthur Hiller
 
21.
Being There (1979)
    1 2 3 4 5 6 7 8 9 10 8.0/10 X  
A simple, sheltered gardener becomes an unlikely trusted advisor to a powerful businessman and an insider in Washington politics. (130 mins.)
Director: Hal Ashby
 
22.
Date Night (2010)
    1 2 3 4 5 6 7 8 9 10 6.3/10 X  
In New York City, a case of mistaken identity turns a bored married couple's attempt at a glamorous and romantic evening into something more thrilling and dangerous. (88 mins.)
Director: Shawn Levy
 
23.
Whistling in the Dark (1941)
    1 2 3 4 5 6 7 8 9 10 6.9/10 X  
Radio crime show host 'The Fox' along with his fiancée and ex-girlfriend are kidnapped by a larcenous cult who demand that he help them plan a perfect murder. (78 mins.)
Director: S. Sylvan Simon