A Skydiving Cameraman Looks Back on His Career

If you were to find entire dinette sets, automobiles and living rooms — with people sitting in them — tumbling Earthward from the clouds, you might think “Okay, so End Times really are a thing.” But it could also be the handiwork of “Space Cowboy” subject Joe Jennings, a “freefall cinematographer” who’s made a specialty of devising and filming such surreal stunts. Coming a decade after Marah Strauch’s first feature “Sunshine Superman,” about BASE jumping pioneer Carl Boenish (also an aerial cameraman), this new doc provides a thematically and stylistically overlapping companion piece. 

Co-directed with Bryce Leavitt, it’s not quite so exhilarating or moving as its predecessor, perhaps because the central personality isn’t larger-than-life this time around. Still, one can hardly complain, as the pleasantly low-key Jennings earns his living doing activities that make the jaw drop — and they’re all onscreen here. Currently traveling the festival circuit, “Cowboy” should have little trouble finding berths in various formats worldwide.

What is called his “insane passion for dropping large objects from the sky” somehow evolved out of a difficult upbringing in which, after being diagnosed with ADHD, Jennings was sent to a hippie-commune “school.” Then he and his siblings got unceremoniously dumped on a farm to fend for themselves when their parents divorced. After their mother showed up a couple years later to replant them in a suburb, they discovered themselves “not normal” by other kids’ standards. Though the realization of considerable athletic prowess honed by so much outdoor living eventually made him less of a bullying target, Joe still felt the outcast stigma of being termed “Joe Dirt.” 

Heading to college and California in 1980, he met future wife Sissy, who was attracted by his adventurous spirit. Skydiving was on their bucket list, but after one go Jennings knew he could never get enough. By 1990 he was getting into professional “camera flying,” jumping with other divers to film their descents with a helmet videocam. Intrigued by reports of “freestylers” doing elaborate moves in mid-air before opening their chutes, he commenced a partnership with Rob Harris, a DJ, skateboarder, street-bike racer et al. whose flamboyant innovations encompassed “basically breakdancing in the sky.” Riding the then-emergent field of “extreme sports” (the X Games began in 1994), they made waves as a team, Jennings’ photography of Harris’ stunts soon attracting lucrative offers to stage commercials, TV and movies. 

It was a “full-on bromance” that crashed to a halt in 1995, when Harris suffered a mortal rig-malfunction accident on a Canadian shoot. Even before that tragic event, Jennings had bouts of melancholia; he found fame had to take. The mental health issue hit again, harder, after French skysurfing pioneer (that’s aerial freestyling with a snowboard) Patrick de Gayardon — with whom he’d begun a new ongoing collaboration — met a similar end to Harris’ in Hawaii three years later. 

Jennings’ spouse discusses these struggles, as does eldest son Joey, who at a certain point realized he too is at risk for clinical depression. But however variable his mood on terra firma, dad is still supercharged by his work in the ether, that excitement encapsulated by the observation, “Here I am, 61, and I have not grown up at all.” 

Apart from the chronologically-told biographical narrative, “Space Cowboy’s” principal structuring thread is Jenning’s team’s quest to perfect “the Holy Grail of flying objects”: Fine-tuning a car found in a junkyard so that it can be dropped from a plane and filmed as it plummets without flipping, spinning or tilting. (Or hitting a cameraman, as happens in one test run.) Of course it must also carry passengers, who’ll trigger their parachutes at the last possible second. We never learn just what this is for… but does it matter? Jennings calls these flabbergasting feats of aeronautic engineering “art,” and indeed they are, no less than Andy Goldsworthy’s ephemeral sculptures or Christo’s temporal wraps. 

While their main figures are of different generations, “Cowboy” mostly sticks with “Sunshine Superman’s” winning soundtrack strategy, heavy on pop rock of the Me Decade via sweet-spot cuts from Three Dog Night, ELO and Big Star — though there’s also room for Fugazi and Eels. Archival footage (including much of Harris) reflects the disparate video quality of earlier decades. Given the deep pockets of the participants’ employers, from MTV to Pepsi to action blockbusters like “XXX” and the first big-screen “Charlie’s Angels,” however, they’re pretty high-quality — as is the new material shot by Tony Johansson.