The 2025 Dialogues Documentary Film Festival had its second day Friday with some fall rain coming in following the last showing of the night. A noticably larger crowd showed up for SPACE COWBOY as well.
SPACE COWBOY is essentially the story of Joe Jennings who has a unique career of being perhaps the greatest skydiving cinematographer in the world. You’ve probably seen some of the footage he’s shot. He’s a loving family man. And he’s had to deal with loss and clinical depression.
Perhaps solely due to his career, there’s a wealth of spectacular footage, much of it thousands of feet off the ground. Joe was the cameraman on the team that won the first Extreme Games, later named the X Games, competition in sky surfing. While there is an element of danger, as explored in the film, the program book’s comparisons to FREE SOLO aren’t one to one. There’s a rush to be sure, but safety is also in mind. Especially since this isn’t a solo pursuit, these skydiving competitions and stunts are decidedly a collaborative effort and it would be no accomplishment if all parties didn’t return.
And the movie doesn’t shy away from when things go wrong. And the effect it can have on a survivor. Especially when the survivor suffers from clinical depression. That section is some of the most moving material in the film.
It’s also paired with Joe planning a new stunt involving dropping a car out of a plane and riding in it for a good portion of the drop. It leads to some nice footage, but no stakes are ever established. It’s entertaining enough, and the procedural planning aspects are interesting, but the whole subplot is kind of a “so what” shrug. It ends up feeling like an attempt to give a film a climax that just isn’t there in the story.
The 2025 Dialogues Documentary Film Festival runs from September 18 to 21, 2026. Further information on the festival, and films that screened can be found at Milwaukee Film’s website.