'I've Had So Much Fun With Cops'

NOT showing at NBFF: Pray for Me: The Jason Jessee Movie

In 36 years, Jason Jessee has been a Mormon, a lowrider, a husband and father, an outlaw biker, a small-business owner, a pro skateboarder, and now the star of his own documentary: Pray for Me: The Jason Jessee Movie. Years after the royalty checks ceased, he remains a cult hero of mythic proportions to his peers for his incandescent ability to achieve the insane and the impossible—without seeming to try.

“I could see just a silhouette of him doing a frontside ollie,” says skate king Tony Hawk, “and I would know it was him. He went higher than anyone, and he just had a certain style.” Hawk remembers going to keggers with Jessee in the ’80s—and how much Jessee hated paying admission to a house party. So, Hawk says, “he would always steal the TV remote controls from the house.”

“It was,” Jessee says of his skating style, “just the whole not caring—the complete, just, not caring at all and making it.” With a certain nihilism at his back, he earned a deserved reputation as the first skater to get full-sleeve tattoos, the first skater to wear Dickies and Pendletons and drive custom cars and outlaw choppers—and the only white guy ever to join the Dukes lowrider car club, a Latino stronghold.

A date with destiny. Photo by John Gilhooley
A date with destiny. Photo by John Gilhooley
In Watsonville. Photo by Theo Douglas
In Watsonville. Photo by Theo Douglas

But through it all, Jason Jessee has also had a more sinister label. Because of what he does and how he does it, he remains what law enforcement refers to as a “person of interest.” Sometimes he eludes them—by hiding, by talking his way out of a jam, or by having friends intercede on his behalf. Other times he loses and, as he did in January, winds up on the evening news and the national no-fly list. “[I’m] the biggest successful failure ever,” he tells me at one point; his whole life has been a dance marathon with the cops. And waiting to cut in? Are more cops. It never ends, partly because he can’t stop it, partly because he doesn’t want it to.

“You can create your own destiny,” Jessee says, “and I’ve had so much fun with cops.

“I remember once I was 15, in 1985, and I was in Alabama. It was my first amateur [skateboard] contest I went to out of town, and I rode for Vision. I got the rental car from—Gator [Rogowski], I think. I went up the center divider—I didn’t see it, and then I turned into this fenced, grassy area and just started spinning doughnuts, like a ton of them. And then I took off and went off to the contest. And then these feds showed up. They came in with full-on lights and everything.

“And they were asking everybody where I was, and they were like, ’We don’t know where he is,’ and it turned out that where I was doing doughnuts was federal land.” Vision founder Brad Dorfman talked the federal agents out of taking him away. “Then later that night,” Jessee says, “I got everybody kicked out of the hotel . . .”

People can’t believe he’s lasted this long.

“Skateboarding has a punk edge to it, and his heroes were all pretty much fucked people,” says former pro skater Mike Lohrman, 38, of Newport Beach. “He followed along in their footsteps.” On the wings of a wicked air-to-fakie, that frontside ollie and a few other choice moves, Jessee turned pro for Santa Cruz and moved out of his parents’ San Juan Capistrano house the day after he turned 18—Dec. 29, 1987. But his best showing was placing third in a world halfpipe competition, and the year he made $100,000—his biggest-ever money—it just blew away.

“I have no fucking idea [where], and I was really super careful with not blowing it, but I have no idea. But I got a lot of good new friends that year. I’m too ‘Share the Wealth,’” he says, referencing the platform of demagogical Louisiana governor Huey P. Long, who was assassinated in 1935. “And then taxes killed me. I got fucked. I got audited later.” Now he rents a warehouse unit in Watsonville where the toilet barely works. A cold wind blows in the roll-up door, and it smells like Bandini. On the other side of the wall is a towing company he swears is a front for the cops.

“They’re not a tow truck company. Who would have a towing company here? And the cops are always in there,” he says—sounding like he does in the movie, where he talks about chem trails and scans the sky for helicopters—with a pair of binoculars his mother used to look for UFOs. Because, he says, when he moved in, the towing company was set up as a fake chop shop for a sting, and it was lousy with cops. Why would they leave now?

“The first week I moved in there, I looked out the window and I was like, ‘I’m getting raided.’ There were so many police and FBI agents over there, I was like, ‘I’m not ready, but I guess I’ll let them in.’ And then this guy comes over, and he’s like, ‘Are you Jason Jessee?’ And I’m like, ‘Yeah.’ He’s like, ‘Hey, I’m in this car club . . .’—he’s like, ‘You don’t have to move out, we’re leaving. This is our last night.’” It was very Drugstore Cowboy—the scene where the junkies see flashing lights, crack the motel door and find a sheriff’s convention outside.

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