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‘Skate Or Die,’ A Coming-Of-Age Documentary Set In Little Village, Debuts In Chicago Saturday

The feature, more than 10 years in the making, chronicles the young adult years of Little Village resident Leo Castillo as he navigates life on the Southwest Side through skateboarding.

Skate or Die chronicles the life of Little Village resident Leo Castillo as he navigates the challenges of the Southwest Side through skateboarding.
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LITTLE VILLAGE — A documentary highlighting one Little Village teen’s coming-of-age and the importance skateboarding played in his and his friends’ lives gets its long-anticipated Chicago premiere.

The film, “Skate or Die,” was a work in progress for over 10 years. It premiered at film festivals last spring, director Ryan Ferguson said. It is playing for the first time in Chicago Saturday at the Music Box Theater, 3733 N. Southport Ave. Tickets for the 4:15 p.m. showing can be purchased here.

Ferguson said the inspiration for the film struck him after reading a 2007 Chicago Tribune article by Azam Ahmed, who now works for the New York Times and was also the film’s writer and producer. The article highlighted the rise of skateboarding in urban communities where it hadn’t previously been popular — like Chicago.

“This story really flipped it on its head and was talking about kids growing up in the midst of some pretty intense gang violence and pretty strict gang boundaries in their neighborhood, and that the skateboard was giving them this both metaphorical and literal vehicle to cross these boundaries and meet people from all over and see the city and like you know, offering them essentially an escape,” said Ferguson, who’s lived in Chicago for over 20 years.

The documentary centers on Leo Castillo from the age of 17. He is a Little Village-raised teen who’s navigated his difficult life with skateboarding as an outlet, but whose future begins to seem uncertain when he’s shot in the leg by a stray bullet.

Ferguson said he hopes the film uplifts the positive work that many people and organizations in Little Village do to make the community safer and more prosperous. One of the groups highlighted in the film is Enlace.

“As much as there’s a thread of the story that’s about gang violence and all these things that I feel it’s so easy to kind of demonize the community with or portray unfairly, I really spent years working to show Little Village in its full glory,” he said. “It’s really celebrating the community and the people and the heart and the fight that Little Village has to make their community a beautiful place in the face of all of these challenges.”

Following Saturday’s premiere at Music Box, figures from the movie, both on- and off-screen, will speak on a panel hosted by WBEZ’s criminal justice reporter Patrick Smith.

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Director Ryan Ferguson said his inspiration behind the film was a 2007 article in the Chicago Tribune that highlighted the rise of skateboarding in communities where it hadn’t previously been popular.

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