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A term used to mock the hairstyles of two characters from the anime Katekyo Hitman Reborn!. Mukuro Rukudo and Chrome Dukuro's hair have spikey point in the back heads, and therefore they look like pineapples. Fans of the show tend to draw and doodle Mukuro and Chrome with pineapples.
Check it out. I just drew the pineapple heads on my history homework.

Niiiccceee.
Juudaimeによって 2009年11月11日(水)

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deragatory for Hawaiian islander by a haole
Those pineapple heads think that they are God's gift to the rest of the US.
pIn a-puhl hedによって 2003年09月21日(日)

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Someone who is really really smart but at the same time really really dumb. They suffer from severe confusion when encountering two people with the same name. A Pineapple Head loves video games and eating pineapples. He/She is not rude, but will occasionally make a poorly timed comment. Overall good guy, just suffers from being from Hawaii.
"Poor planning.
Wow dude way to be such a pineapple head."

"Wahh I'm hungry.
Typical Pineapple Head bullshit."
bronybroによって 2011年03月06日(日)

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Someone with an abnormally large head oblong in shape with a faded hair cut with either a But cut (Parted down the center) or spikey hair.
Homer Simpson, Bart Simpson. Used in a sentence "Hey Copernicus, why don't you take your Pineapple Head and your parachute pants and navigate to the back of the line, standing there in your bowling shirt and your plantar fasciitis"
The guy who bones Tony's momによって 2014年05月02日(金)

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one who wears their hair in a high pony tail on their head (some times in a bun).
Often of the "popular crowd"
lorによって 2003年09月21日(日)

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Nickname for Hugo Chavez, the dictator Venezuela, because he has a big ugly head that resembles a pineapple.
Ol' pineapple head denounced the US for the millionth time yesterday.
Boogers MeGeeによって 2009年04月05日(日)

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someone with an abnormally enlarged head who is stupid.
that kid has a frickin pineapple head.

kit is a pinapple head

dude, spongebob could live in there
eli aによって 2006年05月10日(水)

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