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You can stream Flyin' Ryan (2003) on Shout! Factory Amazon Channel with a subscription.

When twelve-year-old Ryan is forced to move to a new town, he soon discovers the kids there are mean and tough. And they really don't like strangers. Ryan is given a strange pair of magical shoes and finds that the sky's the limit.

This low-budget fantasy captures the awkward, lonely magic of being a kid in a town where everyone wants you gone. Once those enchanted sneakers take flight, the mundane struggle of middle school transforms into a literal trip above the clouds.

Trailer