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Originates from the movie Vanilla Sky. When your f-ing a chick and you confuse her with another girl, but continue to have sex with her (usually even harder).
I pulled a Vanilla Sky last night; I was having sex with Racheal, but then I thought it was Lindsay, so I used the moves I that pleasures Lindsay. It gave Racheal a triple orgasm.
by Trip Aces January 04, 2005
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Nov 27 Word of the Day
A stupid person; it refers to the lack of surface area on an individual's brain. The general thought is that the more surface area (wrinkles, creases, etc.) a brain has, the smarter the person is. Conversely, a person with a smooth brain (no wrinkles) has less surface area and would therefore be stupid.
That fucking smooth brain put his shirt on backwards again...

That smooth brain is dumber than a pile of shit.
by Tip Tank May 14, 2011
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2
A really good movie starring Tom Cruise. It gets confusing a little bit but the climax is amazing.
Let's watch Vanilla Sky.
by sagzag June 22, 2004
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3
Dude: Hey baby you wanna watch Vanilla Sky tomorrow night say around 10.

Girl: Oh yeah. Good thing I took the pill this morning
by Tiger RAARRRR May 02, 2008
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4
i looked up at the sky and a bird poo went in my eye and i say @#$@#$!. screw this @#$#@ vanilla sky
by GXBJB September 22, 2003
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