Wild Man of the Waves

Jamie O’Brien is taking surfing to a new and absurd places
Story by Beau Flemister. Photos by Jake Marote.

Hidden behind a fence along naupaka-lined Ke Nui Road on O‘ahu’s North Shore, Jamie O’Brien is in his backyard packing for a surf trip to Indonesia. He’s got an array of bizarre equipment laid out on the grass, and he ping-pongs from his bowl of ‘ahi on the picnic table to a garage where, with each trip, he unearths some odd new instrument of mischief. A happy black Lab lumbers behind him, fishing for back scratches while random groms (young surfers) drop in and out of the property to say “howzit.”

So far on the lawn there are half a dozen soft-tops (mass-produced surfboards for beginners), towropes, dive fins, helmets, leashes, a deflated rubber raft, life vests, a Banshee Bungee (an accelerative bungee rope), an aloha shirt tuxedo and a leopard-print Speedo. “Everything’s funnier when you’re wearing Speedos,” O’Brien says.

The North Shore’s Jamie O’Brien has carved out a role for himself as surfing’s clown king. For his web television series Who is JOB?, he and his friends travel the world pulling pranks, staging stunts and riding waves in crazy ways. Above, O’Brien at his home break, Pipeline.

Tow-headed with pterygia, those blood-shot bumps on the whites of the eyeball that surfers get, the 33-year-old North Shore local bears a collection of faint scars that map his body like translucent tattoos on a Russian mobster who’s done some time in his day. He wears a constant half-grin that seems to say, “You think I’m kidding, huh?”

He’s not. And for a successful professional surfer like Jamie O’Brien—a guy who’s won nearly half a dozen contests at Banzai Pipeline, one of the world’s most dangerous waves—it appears that he’s bringing everything but the obvious to Indonesia. The obvious being a board bag full of functional surfboards and some actual boardshorts. But that’s precisely O’Brien’s modus operandi.

“These days I’m into riding waves on different crafts,” he says. “For example, riding a twenty-foot wave on an inflatable raft, doing 360s down the face, just totally pushing the limits while having more fun with more friends. The more the merrier.”

O’Brien explains that he and his boys are trying to get to a wave near Bali, one of the better lefthanders on the planet, to film there for the newest season of his hit show for Red Bull TV, Who is JOB?

He’ll be going with a crew of about ten friends and filmers. Jet skis will be waiting for them. And at the moment he’s trying to figure out whether to bring the SUPsquatch, a monstrous, seventeen-foot-long stand up paddleboard that can accommodate eight full-grown men. In one episode of Who is JOB?, O’Brien and his crew managed to paddle into thirty-foot waves at Mākaha and Waimea bay on this absurd craft—and survive.

Tandem kayaking in giant surf, setting himself on fire before getting barreled at Teahupo‘o, catching waves on all sorts of craft ill-suited for the purpose — these are the sort of antics O’Brien revels in. Yet sometimes he still surfs the old-fashioned way. Above, O’Brien rides Waimea bay during the 2016-2017 Quiksilver in Memory of Eddie Aikau Big Wave Invitational.

At said wave in Indonesia, O’Brien wants to attempt tandem surfing with his co-star, Sean “Poopies” McInerney. He also wants to “big wave raft” another wave in Bali, swell pending. Neither feat has been done before at these breaks; “never done before” is pretty much a requirement for the stunts that make it into O’Brien’s show, which is filming its seventh season.

“My goal is to go to all the same spots as surfers but have way more fun there,” O’Brien says. “We want to … what do you call it when you charge at someone with a pole?” “Joust?” I suggest. “Yeah—we want to get mopeds and joust on the beach in Bali,” he smiles earnestly. “We’re entertainers, plain and simple. People already know that I can surf Pipeline, so we’re just constantly figuring out something different for viewers.”

An image of O’Brien jousting with an opponent on mopeds at a random beach in Bali is the kind of thing one might expect to see on Who is JOB?. A web television series with six nine-minute episodes per season, and with Red Bull TV’s high production values, Who is JOB? is part adventure travel show, part MTV’s Jackass, with a healthy dose of professional surfing, too. O’Brien is one of Red Bull’s top athletes and a sort of uncertified stunt coordinator. The feats he stages walk a precarious high wire between hilarious and terrifying.

For instance, O’Brien, Poopies and crew (a handful of other pro surfers from the North Shore) have gotten in an inflatable hamster wheel at Pipeline and caught waves most surfers would balk at. They’ve set up summer camp–style inflatable water blobs at Waimea bay and bounced each other high into the troposphere. They’ve invented mattress surfing (riding on an actual bed mattress), hedge surfing (riding on manicured bushes), big-wave rafting (just what it sounds like) and more. If the waves are flat, they’ll bust out their gas-powered winch or Banshee Bungee for added momentum on, say, a fifty-yard-long Slip ’N Slide ending in the ocean. They’ve brought snow to the beach, hauling a truckload of ice shavings from Honolulu’s Ice Palace skating rink to the North Shore, so they could literally snowboard on the sand.

Above, O’Brien and company after a session at Pipeline with soft-top surfboard, SUPsquatch and inflatable raft.

It’s hard to find an extreme adventure that hasn’t been done in Hawai‘i, but O’Brien has been doing it for seven seasons now. Every year, he takes the show on the road, too. In an episode from season five set in Tahiti, O’Brien lit himself on fire in a stunt suit and surfed big waves at Teahupo‘o, totally ablaze.

O’Brien’s role as content creator turned internet star developed as a shrewd career move in surfing. Born and raised on the North Shore, O’Brien grew up in a home a hundred yards from Pipeline, the most photographed and pursued wave on earth. Over the years, he’s broken both legs in wipeouts there, won the coveted Pipe Masters contest and four other events. He is matched at Pipe only by world champions Kelly Slater and John John Florence.

But what O’Brien and few other pro surfers had the foresight to do (before everyone started to do it) was produce their own movies and web clips. By 2009 he had made three feature surfing films. But he was at a fork in the road in his career, facing one of what seemed like only two paths: Join a thousand other pro surfers grinding it out on the contest tour, or hope for a photo trip for a magazine. In an act of defiance (and savvy theatrics), he lit the official rulebook of the Association of Surfing Professionals (now called the World Surf League) on fire at the beginning of his third surfing film, Who is JOB? “I was definitely a little arrogant and outspoken when I was younger,” he says. “I think I spoke freely about the surf industry and contests, and that can get you in trouble. But when I burnt the rulebook I just wanted to let people know there was another path out there. You can surf without rules. It doesn’t have to be in contests.”

Leaping from the rock in Waimea bay, O’Brien attempts to catch the wave below — a move called an “acid drop.”

Thus O’Brien forged his own path, parlaying his 2009 film, Who is JOB?, into a Red Bull TV internet sensation. While showcasing his surfing as one of Red Bull’s marquee athletes, the mission was also to just have fun. O’Brien’s idea of fun, that is. Which, for most, would be utterly terrifying. But O’Brien knew it’s precisely that type of fun that viewers can’t take their eyes off of.

“There really isn’t anyone else that could pull off and create the show that Jamie does,” says Zander Morton, Surfer Magazine editor-at-large. “I can remember one year when he was on three different magazine covers after the Pipe Masters. He’s a legit pro surfer. He’s taken an abnormal avenue as far as surf careers go, but he’s managed to build an entire name around thinking of entertaining, crazy adventures.”

“We’re always figuring out how to make the show relatable,” says O’Brien. “To me, surfers like John John and Kelly Slater, they’re so good and freakishly talented that it can be hard to relate to them. But with what we do—using soft-tops, or getting towed into waves on inflatable rafts, or surfing in sumo suits—kids can laugh at that and replicate the fun in their own way. People can relate with fun, and I think the surfing world needed that.”

Make no mistake, not just anyone can do the stunts that O’Brien and his crew do. Growing up in front of Pipeline, winning contests there and being one of the best to have surfed the wave, O’Brien’s earned the right to cause a little backyard ruckus.

“I think we have the green light to do some of the stuff we do out here. But we don’t do it all the time,” he says. “We strike it. We don’t cause trouble every day. We cause trouble for a couple days.” He laughs and pets his dog. “And usually when you’re having fun, you’re causing a little trouble. It should be illegal to SUPsquatch. It’s that much fun.”

O’Brien shooting the rapids at Waimea. “People can relate to fun,” O’Brien says, “and I think the surfing world needs that.”

I ask O’Brien if he and his crew ever get pushback from surfers when they show up at a place like Jaws on Maui to surf soft-tops. Some surfers have spent decades training for epic days that O’Brien might show up to in Speedos and water skis. “People have gotten a little mad now and then,” he grins. “Let the haters hate, I guess. I think we bring a lot more positives than negatives. And at the end of the day, we’re just having fun. People eat that up.”

“Like other big-wave guys, Jamie is missing that fear gene, but he takes it to another level where he’s not only unafraid, he’s actually having the most fun in the hairiest conditions,” says Chas Smith, a surf writer and author of Welcome to Paradise, Now Go to Hell. “Jamie will be laughing while other guys are white-knuckling. But it’s definitely that element of levity that he brings to terrifying situations, rather than a serious, grave approach, that has made the show so successful. Having fun is far more infectious than being so serious.”

While O’Brien is certainly a compelling host and comfy in front of the camera, much of this “fun” of which they speak is owed to Sean “Poopies” McInerney, O’Brien’s Sancho Panzaesque, easily coerced crash test dummy. O’Brien discovered the Carlsbad, California native along with five other “Daryls” (derelicts) squatting in the basement of a beachfront home he had recently bought. At the time, O’Brien was renting the house to surfers, and when he discovered a room meant for two was filled with a half-dozen futons, he ordered everybody out. But Poopies, insisting that he would earn his keep, persuaded O’Brien to let him stay. And he’s been a part of the show since the beginning.

It was a particularly daring stunt in season two that put both Poopies—and the show itself—on the map. In an attempt to go “sewer surfing,” Poopies slid down a hundred-yard-long drainage ditch in central O‘ahu on a finless surfboard. The stunt set the show on fire and got 13 million views on the drop.

Sunset at Pipeline, the break in O’Brien’s backyard. He grew up there and it remains the wave he knows best.

“My dynamic with Poopies on the show is perfect,” says O’Brien. “It’s salt and pepper. I put him in situations that he doesn’t want to be in, and if he’s too scared —which is rare—then I’ll join him. These days 99 percent of fans’ first question for me is, ‘Where’s Poops?’”

I ask O’Brien if he’s ever considered leaving home to produce a larger project on the Mainland, if “going Hollywood” was ever in the cards. He pauses from packing for Indonesia, outstretches his arms and looks around to emphasize his point. “Hawai‘i is paradise,” he says, shaking his head. “No matter where I go in the world, it’s just sooo good to come home. There’s everything here for an adventurer. Free-diving, fishing, scuba diving, hunting, sailing, swimming with dolphins—there’s too much to do.”

“I never saw this path as an option for Jamie, nor anyone ten years ago,” says Smith. “He totally gave his career a whole new half-life. Honestly, I would not be surprised to see Jamie O’Brien host late night TV or have a cooking show. I could easily see him side-slipping out of surf when his show is done and getting picked up by a network to host a travel show.”

Perhaps then he’ll put the leopard-print Speedo on the shelf. Or not. HH