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This expression is supposed to imply a juxtaposition of a crass or offensive action against something that is held as sacrosanct by someone else.
Coined by Ben "Yahtzee" Croshaw
"For four, what the fuck happened to Clive Winston, you pricks?! In his place we've got some multicoloured, giggly J-pop creature, and you can't play classic rock with that...thing. It's like cock-slapping the Mona Lisa."
-Ben "Yahtzee" Croshaw in his Guitar Hero III review
A sex act when a young "artist" tricks an old dirty art teacher into holding up a empty picture frame. He then shoots "patronage" (i.e. semen) all over her face through the frame, and earns his A.
Hey Phillip i heard you got frisky and game Mrs. C the ol' Mona Lisa Twist durring break
The notion that while there isn't necessarily something wrong with someone/something, the two elements aren't a match.
"Dude, why did y'all break up?"
"Classic Mona Lisa Principle. She was beautiful, mysterious, and intriguing, but (pointing to my brain) didn't match a damn thing in my house."
When you put your fist in her ass hole and your cock in her pussy then give yourself a hand job
I gave myself a Mona Lisa handshake last night, it was a beautiful disaster.
To mona lisa is as if one embodies a famous painting, becoming a still, quiet, person on the wall just hanging there and when you want to either scare rob or sneak up on a nigga then you being the painting actually jump off the wall and attack or do whatchu gotta do Mona.
Ok pal, you go in there and assume the possition til i get home boy in this bitch and when i say the magic word you gonna mona lisa this bitch take his money and keys then we gonna run.