TIFF 2024 'Space Cowboy': Famed skydiver Joe Jennings gives us an intimate look into his inspiring life

From life's biggest triumphs to most upsetting tragedies, Bryce Leavitt and Marah Strauch's film Space Cowboy looks at the life of skydiving cinematographer Joe Jennings. Making its premiere at the Toronto International Film Festival (TIFF), Space Cowboy looks at how Jennings teamed up with the late Rob Harris to pioneer aerial tricks, while Jennings also opens up about growing up with ADHD and his battles with depression.

"The first thing that just caught my eye was this career he had that I didn't even know existed," Leavitt told Yahoo Canada about why he was interested in Jennings' story. "You can't exactly go to your local community college and enroll in aerial cinematography classes."

"Then as I got to know Joe and built a little bit of a friendship with him, I realized just how endearing and intimate of a human being he was with some of his struggles, with mental health and some of his passions, and some of his obsessions. I was fascinated by the world and by him."

Space Cowboy chronicles Jennings' life from growing up in New Jersey in the 1960s, eventually moving to California and trying skydiving for the first time, and later winning first place at the ESPN X Games with skysurfing partner Harris. Now married with children, Jennings has also worked on a number of Hollywood films and commercials.

This documentary impressively blends archival footage, much of which Jennings took himself, with interviews conducted for the film.

"He started picking up a camera in his 20s, so we had this breadth of footage that was him when he was going through depression, when he was having children," Strauch said. "The balance was really being able to find moments where we could empathize."

"A lot of people don't understand skydiving. I make a lot of films about sports that aren't about sports, and I think this one really fits into that, in terms of wanting it to play to an audience that's not only an extreme sports audience, but also people ... who don't skydive, ... who are not even athletes."

'I think they realized this would help other people'

What's particularly impressive about how Jennings' story is told in Space Cowboy is how open an honest he is throughout the film. That includes really candidly speaking about how classmates would call him "Joe Dirt" as a kid in school, and when he achieved a significant amount of fame he still felt like "Joe Dirt" inside. That openness also extended to conversations about Harris' death.

"I think the main thing that drove that was just trying to stick to the truth, and not trying to sensationalize things," Leavitt said. "Not trying to add my own agenda as a writer to things, but just really talk to the people that were around this situation, and let them just tell their truth, and let that guide the conversation."

"But it was a heavy thing. It was definitely a heavy atmosphere on set that day, you could just feel it."

"A lot of the films that I've dealt with making have to do with a death and have to do with grief, and have to do with life though, too," Strauch, who also made the film Sunshine Superman, added. "I really appreciate Joe's willingness to go into this, because ... this is something that people do not talk about enough, and I think it's really important to talk about it in a way where we can really explore what it's like to grieve somebody."

"Our hope was that grief is really relatable and can help other people."

When it came to Jennings speaking about depression, he's particularly detailed and honest about how he's felt, including the impact it's had on his family, including his children. A key to that was also getting the perspective of his wife, Sissy.

"You're asking people to go to some of their most intimate memories and some of their darkest times, and going to some places that they don't probably naturally want to speak about, so it's obviously a delicate process to do that, but I think it was super important to the story," Leavitt said. "Sissy, who's Joe's wife, is kind of the key to unlocking that entire puzzle."

"A lot of people were like, 'We don't need her story. Why are you telling her story? What's going on there?' And I'm like, I think her story is central to Joe's story," Strauch said. "I think what Sissy's [story] really does in terms of depression is talk about what it's like to also be the other person who cannot grab that person from the depths of hell and get them to come out of their depression."

"I think that's so powerful and I think their family dynamic is so powerful. ...I also really commend Sissy, because she's very quiet and soft spoken, she was able to really go to places that were really surprising to me as a filmmaker. It was a really special thing and I think they realized this would help other people."

'It is a happy story'

But with all the turmoil in Jennings' life, Space Cowboy still maintains all the thrills and excitement of a skydiving documentary, leaving you with a sense of hope and joy.

"Life isn't just a drudgery of sadness, and it's also not just this huge explosion of happiness at all times," Strauch said. "I think in making films that reflect life, which are documentaries, you really want that kind of salty and sweet kind of sense of joy and sorrow, because that's being alive."

"The truth of this story is it is a happy story," Leavitt added. "Joe's line towards the end of the film is, 'My glass is 99 per cent full,' that's how he views these extreme highs and these extreme lows that he's been through."

"He still has a lust for life and he still has a passion for his art and his family and things he's doing. ... That doesn't mean he's not immune to the low end of things, it's just that he's found a way to navigate it in a way that I find not only endearing, but inspiring."