Caple Jr.’s feature film debut The Land premiered at the 2016 Sundance Film Festival, where it was acquired by IFC Films. It tells the story of four teenage boys who devote their summer to escaping the streets of Cleveland to pursue a dream life of professional skateboarding. The film was released on July 29, 2016. Caple Jr. would go on to be named by The Playlist as one the 25 best breakthrough Directors of 2016.