The epitome of the classic gentleman is and will always be Cary Grant. No one wore a tux like him, no one could charm the socks off of the world like him and no leading man has ever come close to his effortless elegance — sorry Clooney. And for that very reason, there are no Cary Grant films on this list of Essential Viewing for the Fashionable Man.
Because you could watch him in anything — To Catch a Thief, North by Northwest, Charade, The Philadelphia Story, His Girl Friday, The Awful Truth etc, etc, — and know exactly how a fashionable gentleman should walk, talk, dress, act and pratfall. Grant loved him a good pratfall.
Rather, the following films extend the vocabulary of the gentleman beyond sophisticated dinner parties, beyond immaculately-tailored suits, beyond Cary Grant. Not to say that those things aren’t covered in these 20 films, but some times you have to get your hands dirty while still looking so fresh and so clean-clean.
Humphrey Bogart in Casablanca (1942)
Bogie did wonders for the trenchcoat as surly bar owner Rick Blaine, and showed stoic grace in the face of unrequited love for Ingrid Bergman‘s emotionally-torn Ilsa Lund.