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“You used to be able to tell the difference between hipsters and homeless people. Now, it's between hipsters and retards. I mean, either that guy in the corner in orange safety pants holding a protest sign and wearing a top hat is mentally disabled or he is the coolest fucking guy you will ever know.”
― Chuck Klosterman

“I was a hip kid. When I saw Bambi it was the midnight show.”
― George Carlin, Brain Droppings

“Hobbes: What are you doing?
Calvin: Being "cool."
Hobbes: You look more like you're being bored.
Calvin: The world bores you when you're cool.
Hobbes: Look, I brought a sombrero! Now we can both be "cool."
Calvin: A sombrero?! Are you crazy?! Cool people don't wear sombreros!
Hobbes: What fun is it being cool if you can't wear a sombrero?”
― Bill Watterson, Something Under the Bed is Drooling

“Mr Davis was a middle class tremble of a man worried about an unseemly display and his Jerry Springer moment”
― Saira Viola, Crack Apple And Pop!

“It hit me that being hip was a full-time job, and I was only a part-timer. I couldn't hide forever that I liked county fairs, particularly the goat booth at the 4-H tent, or that I once spent a week with my grandmother at her house in the giant retirement community of Sun City, Arizona, and it was one of the most carefree times of my life.”
― Jancee Dunn

“They pine for the hip, frosty girlfriend they abandoned for a pleasant if unexciting marriage to her sunnier, less mentally present sister coast.”
― Sari Botton, Never Can Say Goodbye: Writers on Their Unshakable Love for New York

“Coolness is not an image that can be bought or worn. True cool is an attitude that is projected from a person who is extremely comfortable in their own skin.”
― Suzy Kassem, Rise Up and Salute the Sun: The Writings of Suzy Kassem

“Irony and hip ennui are extremely authoritarian.”
― David Foster Wallace

“The circumference of your breast may change; the shape of your hips may change; the size of your pants may also change. But your life never changes unless your thoughts, your plans and your actions change! Think big things!”
― Israelmore Ayivor, Daily Drive 365

“I do not recall our Lord ever saying one could not be 'cool'. It is only a problem if one esteems 'coolness' above that which is righteous and true, which is, when we give it its way, really what many of us do. 'Coolness' is too transient to be of any real and meaningful, lasting significance, and it is often in great conflict with one being one's most honest, most vulnerable self. That, and in reality, some of the coolest people are actually those who least concern themselves with being cool anyway, those who make 'trying to be cool' less evident.”
― Criss Jami, Healology

“God is not boxed with, nor is He boxed in: And ironic it is, how even what a culture may consider to be 'young and fly', to Him, might've already become 'safe and predictable'.”
― Criss Jami

“It's cool to be cold.”
― Anthony T. Hincks