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Former pro-skater and Bones Brigade promoter Stacy Peralta worked as the Second-Unit director and consequently shot all of the skate sequences for the film.
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Pro-skaters Mike McGill and Rodney Mullen were the stunt doubles for Christian Slater.
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The film crew put flint in the skater's trucks so they'd spark when they would grind.
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There is an Easter Egg on the DVD containing a skateboarding documentary.
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The high school scenes were filmed at Woodbridge High School in Irvine, California in early 1987. Although Christian Slater and members of the cast are seen skateboarding on campus (by permission of Woodbridge High School principal Greg Cops), in actuality Woodbridge High School has a strict policy that bans skateboarding on campus.
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Former pro-skater Tommy Guerrero made $500 per day teaching Christian Slater how to skateboard.
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When Brian's friends see him on a bike instead of his skateboard, they joke about how he'll be riding around on a scooter next. In The Legend of Billie Jean, Christian Slater played a character whose most prized possession was a scooter.
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Disneyland landmarks the Matterhorn Bobsleds, Mark III ALWEG Monorail, and original Disneyland sign can be seen in the film. Also seen are banners on Anaheim streetlights promoting Disneyland's "State Fair '87" promotion.
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While Brian and his friends are on the plane, his friends start applying skateboarding stickers to the plane's windows. One of the stickers reads "Tony Hawk." Interestingly, Tony Hawk portrays Buddy, one of Brian's friends.
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