Holes director Andrew Davis liked the idea of a prisoner’s song. In the midst of developing the film in the early 2000s, Davis had been listening to a lot of southern Americana music, getting into the spirit of a juvenile correctional boot camp in the Texas desert. As the filmmaking team envisioned the story’s dried-out location and daily hole-digging punishments, Davis couldn’t help but think about instituting a collective melody for his beaten-down characters. “What if we could have something that brought in elements of hip-hop along with the more grounded elements of a chain-gang?” he thought. Perhaps surprisingly, that track turned into a straight-up jam—and is, arguably, the most memorable and enduring part of the movie.
The idea for “Dig It” (as the song was eventually titled) crystallized a few weeks into production, on the back of a bus. Led by Shia Labeouf, the musically-inclined teenage cast had begun freestyle rapping and singing about their orange jumpsuits, calloused hands, and the blistering sun on their way to set. It didn’t take long for producers to hear their creativity and realize they should capitalize on their multi-talented actors. Music supervisor Karyn Rachtman put together a production team of Mickey Petralia and Michael Fitzpatrick to build out a track, reserve a Hollywood studio, and turn the “D-Tent” boys of Camp Green Lake into a legit, hip-hop outfit. “There was really no idea of what it was going to be,” says Max Kasch, who played Zig-Zag. “It came out of nowhere.”
Kasch’s soul-affirming baritone kicks things off against a backdrop of shovels before the hypnotic piano-driven beat drops. Throughout its four-minute runtime, the other members of the D-Tent—LaBeouf (“Caveman”), Byron Cotton (“Armpit”), Brenden Jefferson (“X-Ray”), and Khleo Thomas (“Zero”)—spit verses about their characters (“What’s that you smell? Dog, that’s me”). “It had the actors singing, it had them in character, it was a musical moment,” Rachtman says. “When a song is really created for the film and about the film, it's a lovely marriage.”
Holes, an adaptation of Louis Sachar’s Newberry prize-winning children’s book, earned strong reviews by melding a faithful adaptation with entertaining camaraderie from its young cast, tripling its budget at the box office. But the earworm status of “Dig It” took on a life of its own. Released 20 years ago, the song remains a nostalgic millennial staple. “These things can just go and get lost, but for some odd reason, for anyone who was a part of it when it arrived, it still hits,” Thomas says. “That's how you know we made a classic.”