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7 Old-School Jazz Masters Who Totally Beat You At Being Cool

They're either older than your grandfather or already dead, but you'll never achieve their level of effortless cool. (Brought to you by jazzleadsheets.com)

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1. Thelonious Monk

images37.concordmusicgroup.com / Via Concord Music Group

Style of coolness: Weird hats and incomprehensible muttering

Why he's cooler than you: Your grandma made you that exact same hat, but you were too scared you'd look like such a dweeb if you wore it.

What to listen to: Monk playing his famous composition Round Midnight live in 1966

2. Rahsaan Roland Kirk

rahsaanrolandkirk.net / Via rahsaanrolandkirk.net

Style of coolness: Dark sunglasses and supernatural abilities

Why he's cooler than you: I'm sorry, did you not look at the picture? He's playing three saxophones at once. Did I mention that those saxes are actually modified version of super old-school instruments that he invented himself? And that he was blind? And that he changed his name to Rahsaan because a flash of light told him so in a dream?

What to listen to: This absolutely insane live version of Rahsaan doing his original composition The Inflated Tear live in Prague. It's super out-there, but totally mesmerizing.

3. Art Blakey

s3.amazonaws.com / Via drumlessons.com

Style of coolness: Your crazy uncle who's secretly a total genius

Why he's cooler than you: You've literally never had that much fun at your job. And you probably never will.

What to listen to: Everyone's favorite jazz standard: Moanin', by Bobby Timmons

4. John Coltrane

wordpress.com / Via jazzinphoto.wordpress.com

Style of coolness: That guy who says spiritual stuff that goes totally over your head, but you nod like you agree cause you don't want to look dumb

Why he's cooler than you: He was so talented that some people in (where else) San Francisco started a church that worshiped him as an actual god. What did you do today?

What to listen to: The classic Coltrane album is A Love Supreme, but his rendition of the Broadway tune "My Favorite Things" is loved by many.

5. Billie Holiday

wordpress.com / Via jazzinphoto.wordpress.com

Style of coolness: Making being a tortured soul seem completely glamorous

Why she's cooler than you: No one has ever been able to sound quite like her, but hundreds sure have tried.

What to listen to: You can't go wrong with her take on the standard "Solitude."

7. Miles Davis

newyorker.com / Via The New Yorker

Style of coolness: Doing whatever the hell he wants because he knows he defines coolness

Why he's cooler than you: He casually gave birth to coolness. As a result, you can find his likeness on any pseudo-intellectual college freshman's wall.

What to listen to: The only album that people outside of jazz have heard of -- Kind Of Blue.

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