The Skateboard Kid in order

The Skateboard Kid collection is a pair of lighthearted, family-oriented direct-to-video fantasy comedies from the early 1990s centered on young protagonists and magical skateboards. The original The Skateboard Kid (1993) follows lonely new kid Zack, who discovers a talking, wisecracking magical skateboard (voiced by Dom DeLuise) that helps him gain confidence, impress the local skate crew, and rise above his outsider status. Its sequel, The Skateboard Kid II (1994), shifts to 12-year-old Sammy, who uses a flying magical skateboard to become the town's top skateboarder, facing rivalry from jealous thrashers while competing in high-stakes events. Both films blend '90s skate culture, mild adventure, and feel-good underdog vibes with a touch of supernatural fun. 2 films, 2h 53m in all, in release order.

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   The Skateboard Kid

   1993 · 83 min

   No one could be more bored than Zack, the new kid in town with no friends in sight. When a gang of hip, skateboarding thrashers start cruising his neighborhood, Zack hopes his luck will change. But they want nothing to do with him. Then Zack makes the discovery of his life: a talking wisecracking, magical skateboard. And suddenly, skateboarding rises to entirely new heights.

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2. 2
   

   The Skateboard Kid II

   1995 · 90 min

   Take a roller coaster ride full of high octane adventure as 12 year old Sammy takes to the skies. With the help of a magical flying skateboard, Sammy ends up the hottest skateboarder in town. But a group of local thrashers don't like the extra competition. They plot to destroy any chance of Sammy competing against them in a local tournament. But they don't have a clue of what they're up against.

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