Top Definition
"Chillosophy" describes a lifestyle exhibiting the coalition of intelligence, originality, spontaneity, and good-looks in a kick-back or "chill" manner.

The word is modeled after the posse "Chillosophy", a group of trailblazers from The Mont spanning from Irv-Block to Murder Springs who have proved to be the epitome of the word's definition. The crew prides themselves on their unrivaled sense of camaraderie, unparalleled antics, and ability to have fun under any circumstance.

This group's original and pioneered lifestyle has struck envy in lesser groups around the globe. This jealousy has been tied to the 2004 Toolshed Uprising in which thousands of whack-ass-crews began to from in aspiration of reaching Chillosophy's standards. To this day, nobody has held a candle to the original members of the Chillosophy crew: Chris, David, Derek, Ivan, Jason, Jeff, Jon, Robert, and Matt.

Early Roots: "Psk", "Holler"
" Yo son what it is "

" Nothing just practicing some chillosophy "

" Why bother player, unless you're an O.G. it's impossible to master "

"I guess you're right, shucks, i wish i was them "
by Stuart Odyssey May 09, 2006

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