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No matter how cool you are, you will never be as cool as Frank Sinatra stepping out of a helicopter holding a glass of whiskey. History has had a lot of time to be cooler than you, and the enterprising members of the OldSchoolCool subreddit have compiled some of the baddest examples of people being kickass before you were born. Check out some of the coolest below:

A tank instructor, 1984

old school cool tank instructor
(source)

 

Harry Houdini, 1914

old school cool houdini
(source)

 

Michael J. Fox on the set of Back to the Future, 1985

old school cool bttf
(source)

 

Frank Sinatra stepping out of a helicopter with a drink, date unknown

old school cool sinatra
(source)

 

A school dance, 1950

old school cool school dance
(source)

 

The original selfie master, late 1800s

old school cool selfie
(source)

 

Sean Connery, circa 1960

old school cool connery
(source)

 

French girl and her cat, 1959

old school cool french cat
(source)

 

Elvis and Priscilla Presley, Graceland, 1971

old school cool elvis
(source)

 

Rwandan man with Amasunzu hairstyle, 1923

old school cool amasunzu
(source)

 

Marine cadet, 1941

old school cool marine
(source)

 

Neil DeGrasse Tyson in his wrestling days, 1970s

old school cool ndt
(source)

 

Guy in New Zealand actually pulling off a fedora, 1937

old school cool fedora
(source)

 

Businessman skateboarding barefoot in 1982

old school cool skateboard
(source)

 

The cast of The Outsiders (Tom Cruise, Emilio Estevez, Patrick Swayze, Ralph Macchio, Rob Lowe, Matt Dillon, and C. Thomas Howell), 1983

old school cool outsiders
(source)

 

Led Zeppelin singer Robert Plant holding a dove that flew into his hands, circa 1973

old school cool plant
(source)

 

An Iowa radio DJ, 1957

old school cool dj
(source)

 

Lou Reed and Nico, 1967

old school cool velvet
(source)

 

Motorcycle chariots, New South Wales, Australia, 1936

old school cool chariot
(source)

 

Dog with a corncob pipe, 1875

old school cool smoking dog
(source)

Source

20 Awesome Examples of “Old School Cool”

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