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Films capture the embodiment of cool for their era better than most other media. This list highlights the cool factor from bygone eras that can be found in the Criterion collection. I have only listed films I have seen, so please suggest more in the Comments.
While the scene chewing by Tony Curtis and Burt Lancaster are well documented, what really sticks with me in this film is the pre-Internet media engine of New York City it portrays. Sidney Falco grabs the latest edition of a newspaper and flips to the gossip column as obsessively as any social media addict checks Twitter or Facebook today. The backdrop of New York City in this era when newspapers ruled the roost is a town I would very much like to visit.
A great courtroom drama, exploring the seedier side of leisure distractions of the 1950's as we get to the bottom of a murder. The film keeps you guessing as to the validity of the defense's case, so thoroughly that the verdict itself doesn't seem to answer the central question of who was right.
Mike Hammer! Mysterious packages! Femme fatales! This movie entertains from start to finish. It's no wonder that elements of Kiss Me Deadly have found their way into countless imitators, including Quentin Tarantino's Pulp Fiction.
Sterling Hayden is fantastic in this classic heist film by Kubrick. Having the entire Killer's Kiss as a bonus feature is gravy.
What a ride this film gives you. Constance Towers portrays the hooker with a heart of gold as she encounters issues of race, prejudice, mental illness, hypocrisy and above all sex.
The only technicolor production in this set, Charade has its cool factor in spades. The Hitchcockian plot involves an ill-gotten fortune, double-crossing criminals, and a great screen presence by Audrey Hepburn & Carey Grant. If you prefer a lighthearted look at mid-century cool, this is your film.
I challenge anyone to watch this film and not want to be Harry Lime in postwar Vienna. Welles plays a fantastic antihero. The cool style of this film make me happy I live in a climate that gives me opportunity to wear overcoats.
One of two foreign language films in this list, Breathless launched the French New Wave while evoking the American coolness of James Dean and Marlin Brando.
This film serves as a great reminder of the struggles that come alongside any triumph of creativity. It's on this list because Marcello Mastroianni is so damn cool.