Derrick Cabrera (Paul Rodriguez (skateboarder)) has a dream of being sponsored and one day going pro. He is an up-and-coming street skateboarder from Chicago with all the talent but has the world against him. He and his fellow skateboarding friends Cash (Ryan Dunn), Reese (Terry Kennedy (skateboarder)), and Troy (Rob Dyrdek), as well as filmographer friend Mikey (Adam Wylie), spend their days skating at spots around the city, being pursued by cops for skating where they shouldn't be, and planning how to make names for themselves. In Derrick's case, this means landing one special trick on-camera for a sponsorship video that has never been done before, affectionately dubbed the N.A.C. (Not A Chance) by his friends. Unfortunately, the handrail at the local university he needs to practice his trick on has been skate-proofed, preventing him from making that goal a reality.