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Upper Playground 

A streetwear clothing shop originated in San Francisco, California. Sells clothing, hats, and paintings designed by graffiti and/or street artists such as Jeremy Fisch.

Was once a pleasant, local store where sneakerheads and hipsters visited to pick up some semi-expensive clothing. However, once the word got out it became largely commercialized (in San Francisco) and is now a place where soccer moms come to purchase "cute" jackets for their little kids. Thanks to its commercialization, awkward kids and momma's boys now are running the streets of the Bay Area with Upper Playground's clothing, and its reputation is slowly falling into the gutter.
Awkward Kid: Hey guys, did you see my Upper Playground hat? My mom gave it to me for Christmas!
Ex-fan: Man, I bet you don't even know who designed that hat.
Upper Playground by sneakhead December 29, 2009
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Devil's Playground 

Slang for either the city of Los Angeles, CA, or New York, NY (Manhattan).
Many underground rock bands get their jumpstart in the Devil's Playground.

Geneva's Playground 

Zack will go into lust world of sexual fantasies with his cat and friendly transvestites and have lots of butt sex.
SICK JOKE! that we played on zack aka Geneva!

Snake in the Playground 

When a dude has sex with a hot chick in her "pee hole", yes the one she pees out of. Could also be called "droppin' snakes in the playground". That is all.
Hey man, I was with my girl last night. I totally put the snake in the playground. It rocked.

Math Playground 

That site you fuck around with in school
Hey bro, you wanna go play some Math Playground? Ms. Hub's work is shit.

Pimp on the Playground 

A grade-schooler (preferably ages 5-10) that dresses nicely and gets all the girls.
Little Tim will be the pimp on the playground when he wears these clothes.

Katie's Playground 

A small plot of land consisting of land owner, with a mild case of retardation and sickle cell anemia
Man, I feel bad for everybody who has to play at Katie's Playground.
Katie's Playground by topher piner January 31, 2008