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A Skateboarder, usually from white middle class suburbs, that wears very baggy jeans and knee length baggy white T-shirts and big cushony skate shoes. Usually Skates whilst listening to an mp3 player, with hop-hop and gangsta rap playing on it. Smokes copious amounts of weed whilst skating too.

Inspired by the original Gangster Skateboarders from San Francisco and L.A that appeared in numerous skate videos from the mid 90's onwards, performing symetrical tech lines at pier 7, L.A high schools on picnic benches and sacramento spots. The skate sections always had hip hop and rap music set to the skating, with the tricks being landed in time to the beats of the music. Skateboarding was generally technical and progressive, clothing was usually baggy, many of the skateboarders were afro american and hispanic, and generally from poor families living in poor parts of the city and genuine ghettos.

The modern mass pop gangster skateboarder is usually white middle class and usually a well rounded technical skateboarder, with a skateboarding style with much in common with the 'ledge mathematician'.

A skateboarding trick diet of nollie heelflip noseslides, switch tre flips, switch backside heels switch tailslides switch shove it out, nollie flip crooked grinds and switch varial heelflips down small sets of stairs.
Grant Patterson is a textboox example of the Gangster Skateboarder.

A white middle class skateboarder with a baggy white t-shirt down to his ankles. Cap on back to front and baggy jeans. Specializes in the nollie flip and attributed to the pionerring of 'tech-gnar', a closely related skateboard style to the gangster skater and ledge mathematician, only with a diet rich in handrails and double sets.

"Yo dude, did you film my switch tre down the double set?"

"yeah! shit was tight! HOLLA!!!"
by PLG March 17, 2008
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