'I've Had So Much Fun With Cops'

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.

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?

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“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.

And Jessee knows that, for him, the convention outside will last another 35 years at least. He strikes a pose and fires an assault rifle on full-auto for the director in Pray for Me. But off-camera, the director says, “He’s his own worst nightmare.” And Jessee knows that’s not far wrong.

“It sucks that, even not being a full law-abiding citizen—I’m beyond fucking retarded—and I still feel guilty no matter what,” he says. “Because of how much paranoia is bred out there. It’s like no matter what, you’re doing something wrong. You drive by a cop and you wave and they’re like, ‘What are you doing waving at me?’”

One story I hear from Lohrman is that the cops came and arrested Jessee at a skateboard contest after he called African-American skater Ned “Peanut” Brown a nigger.

“I actually talked shit to him, on the top of the ramp,” Jessee says—he says Brown had mouthed off to him before the contest, when Jessee was making nice with his girlfriend. “And the next thing I know, I’m on the bottom of the ramp. He socked me in the mouth.” And even though Peanut hit him first, Jessee got kicked out of the contest. “It was my first humbling experience,” he says. “Anaheim, 1986, and fuckin’ Jeff Phillips won it on acid.”

There was more on the way. After he left Santa Cruz Skateboards, after he left his next job, as team manager of Consolidated Skateboards, Jason Jessee needed money fast. His wife, Heather, had injured her back and couldn’t work, and she was pregnant with their daughter, Scout—so Jessee got a job: waiting tables, at Positively Front Street, a restaurant on the wharf in Santa Cruz. Later, he was downgraded to busboy.

“It was so humbling, but it was the best thing ever,” he says of waiting tables, when I first meet him, in Watsonville. “Because I learned what people go through. I got a total new respect for—cops, even—waitresses.”

Cops. “You gotta come downhere with me to hear this story,” Jessee says; we’re standing, with a couple of dozen of his “closest friends,” in front of a store on La Brea Avenue in Los Angeles, where Vans is launching the Jason Jessee signature shoe. (He says he’s been paid $1,500.)

Years ago, Jessee tells me when we’re out of earshot, he came into a pristine 1960 Mercury Comet—first year they made them. And his friend Vince Everly, who is here tonight, wanted it, so Jason started driving south. The transmission went out, so he had it towed—and the tow truck driver “mashed it in there. And we had it towed again, and the guy backed into the grill. And I’m thinking, ‘This thing was perfect, and now it’s a piece of shit.’” So they ditched it: they got it as far down the highway as they could, which wasn’t very far, and they left it—on the edge of a big drop-off.

“And this highway patrol guy comes to the door and he goes, ‘I don’t want to cause you any trouble. I know you dropped a car off there, and I know you’re going to get it out of there sometime today.’ And I’m like, ‘Yeah, I’ll get it out of there,’ and he says, ‘What time today?’

“So we go down there, and everything is blackened [where it was]. It’s been torched, pushed off the edge of the cliff, and someone has towed it away. So I get back on the freeway and I’m doing 90, 100, 110, and my friend is like, ‘Why don’t you just call it in?’ and I knew I was going to get pulled over—I said, ‘This is quicker.’” Jessee gets pulled over; he tells the highway patrolman—a different guy—why he can’t tow the Comet: because it’s gone.

“By the end, we’re laughing so hard, we were hugging,” Jessee says. “He’s like, ‘If there’s anything to this, I’ll let you know.’”

Then Jessee tells me, “Vince doesn’t believe this story.”

It’s hard to believe anyone could go from there to there to here—but Jessee isn’t just anyone. “Jason’s told me before, you know, how hard it is to live up to [his] rep, because he always has to go bigger in whatever facet,” his friend, car customizer Cole Foster, says. “His rep precedes him; it’s what makes him, but it’s what might kill him.”

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Recently, it almost did. In Watsonville, shopping for socks—Jessee says he only wears his socks once, and he only wears the striped athletic ones that come up over his calves—he said something wrong to a Mexican guy, and the man swung at him with a knife. And as Jessee stumbled out into the street, dodging the blade, it hit him that he was 36, and that this guy—who was arrested later that day, after stabbing someone else—was 19. And that if he, Jason Jessee—who has staked his career and his reputation on pushing his luck—isn’t dead yet, then maybe he’s not supposed to be.

“’Cause I’ve been waiting for this heart attack that never came,” he says, describing the last days and nights of his skateboard/clothing company, the Auto Modown, which he started with a loan from his dad after leaving Consolidated. It failed, and Jessee owed back taxes; he owed his dad $212,000 in start-up money; and he’d stopped paying his rent $40,000 ago. He tried to sleep, tried to die, on a couch: maybe the very one I’m sitting on. “I thought if I laid on the couch, I could will it,” he says. “But I couldn’t.”

What’s next? David Rogerson, the Pray for Me producer, withdrew the film from consideration for the recent Newport Beach Film Festival—where this year’s Best Picture Oscar winner, Crash, debuted—after I got my hands on a copy. He has a friend in the movie business, and, Rogerson says, they want to start hitting “the real festivals—maybe even Cannes.” But if Pray for Me goes to France, Jason Jessee will be staying home. He’s been grounded since Jan. 4, when he was taken off Frontier Air Flight 169 in handcuffs at the San Jose airport, by San Jose police and FBI agents. Passengers, it was reported, had seen him writing in a journal with the words “suicide bomber” hand-written on the cover, “acting bizarrely,” according to the San Jose Mercury News, and “clutching his backpack.”

When the feds strip-searched him at the airport, he bent over and offered it up—Marlon Brando telling the cops, “My old man used to hit harder than that” in The Wild One. Except Brando as Johnny-the-biker had a world-weariness that Jessee still lacks. He walked off the plane apologizing in disbelief. “I really didn’t think it would ever happen,” he says. “I wanted to test the waters. I can create my own reality. I never thought they’d be frist—what is that word?—frisking me.” He considers meeting himself: “I’d hate to be a cop and have to say that: ‘Let me frisk you.’” Jessee thinks about how words sound, and this is the real reason he was busted.

Among the official publications he owns is a copy of the Pocket Partner: a thick, pocket-size paperback with emergency protocols, checklists and contacts for “policemen, firemen, paramedics, doctors, the military, government, and large and small businesses alike,” according to its website, thepocketpartner.com. Jessee likes knowing what people in charge do in certain situations, and so he bought a copy—but he thought the title sounded “like pocket pussy,” so he crossed it out with a black pen and wrote the infamous words “suicide bomber” on the cover. It’s a song by one of his favorite bands, the Highway Murderers. And later, passengers sitting next to him on the plane saw him reading it—and then the cops were waiting for him. He had computer discs on him with artwork for his skateboard company—and miscellaneous rambling letters to himself, which he’d typed out on his ancient typewriter, and assorted other personal documents, and the feds copied everything. They went through his cell phone; they took blood when he couldn’t pee in front of an agent, and they said they’d be making a follow-up visit. And everything he worried about but thought would never happen was finally happening.

It makes him think of San Francisco years ago, when the feds pulled him over outside where a United Nations palaver would take place the next day. His mufflers were rapping—lowriders are notoriously loud—and they said it sounded like machine-gun fire. And so the homeless African-American guy on the sidewalk stood up—he was an agent—and the Asian street racer dude in the Honda pulled in for backup—he was an agent—and when they were done, they both melted back into the pavement. San Jose was part two of that story arc: an ending he didn’t see coming until it was upon him.

“Did you see that police car go by?” he asks, as we stand around outside his warehouse unit in Watsonville. When I leave, a highway patrol car and a police motorcycle are parked at the Chevron a half-mile down. They look like they’re getting gas, but are they? Jessee wonders: “Don’t they get gas at [their own] place?” he asks when I tell him about it later.

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“‘You can’t win,’ they told me—this Georgia cop, when I was 19—‘You can’t win,’” he says—another story of another run-in. “And I was like, ‘I could blow my head off, and then I’d win.’ And he was like, ‘No, you can’t win.’”

Now he wonders about that too.