Return to the Y

Celebrating Hawai‘i’s big moment in skating history
Story by Travis Hancock.

One morning this past April, several rows of giant shark fins mysteriously sprang up from the sand at Fort DeRussy beach in Waikīkī. Onlookers perched high on the balconies of the Hilton and Hale Koa hotels could soon see the oversized fins, made of plywood, joined to a stretch of studwork ribs that gradually sprouted two broad, parallel limbs.

Over the next three days the scooped-out form gained shape with Masonite skin, a raised spine and then, in spray paint, dragon scales, a skull, a face and a pair of big, droopy eyes.

What was this Sphinx-like structure? A solitary wanderer in knee-high socks and beat-up sneakers knew. Kale Sandridge trudged out across the sand, holding under his arm the wooden key to the riddle: a skateboard. Climbing to the top, he planted his board on the edge of the shark fin and dropped in.

The moment was a poignant rerun of a nearly identical scene that had taken place some three decades before. In 1989, the National Skateboarding Association put on a storied skating competition at Honolulu’s Blaisdell Arena, which featured a revolutionary new ramp, the so-called “Y-Ramp” after its shape as seen from above. Unlike the standard U-shaped half-pipes that contestants were accustomed to riding, the Y-Ramp featured a twelve-foot gap in the middle of one vertical wall, daring the skaters to take a leap of faith.

Mark Oblow, a judge for the 1989 “Hell of a Paradise” skateboarding competition, reprised his judging role for a revival of the contest in April. He’s seen here beside an exact reproduction of the event’s original “Y-Ramp.”

Early this year, Thrasher magazine (or, to many skaters, simply “the Bible”) announced that, thanks to major funding from adidas, it would be putting on a commemorative Y-Ramp competition in Hawai‘i nearly thirty years after the original. “We have the opportunity to build this legendary ramp once again!” the announcement post proclaimed. “This should be one for the records and we are stoked to be a part of it!”

The tribute competition was given the same title as the gonzo-style Thrasher article that had made the original Y-Ramp contest famous: “Hell of a Paradise.” And this year, as in ’89, it was Sandridge—one of Hawai‘i skateboarding’s underground diehards—who took the inaugural run. “Me and Kale were the first ones to ride this ramp 30 years ago!” wrote Y-Ramp designer Tim Payne in an Instagram post. “So good to see him still ripping!”

Nearly every detail surrounding the commemorative Waikīkī competition was an echo of history, from Payne and Sandridge’s duplicated test runs to the graffiti on the ramp, painted by the same legendary pro skateboarders who had been finalists in the ’89 contest. The skull was painted by Eric Dressen (a.k.a. Eric D.), the face by Christian “Mr. Air Show” Hosoi, the scaly dragon by original Y-Ramp winner Steve “Cab” Caballero, and the droopy eyes were the unmistakable handiwork of Mark “The Gonz” Gonzales, later named the most influential skateboarder of all time by TransWorld SKATEboarding magazine.

The resurrected Y-Ramp drew a who’s who of skateboarding luminaries, including Steve Caballero (opening spread), winner of the 1989 contest. The ramp takes its name from the twelve-foot gap in one of its walls. Skaters fly—or attempt to fly—across the gap.

The 1989 contest was essentially skateboarding’s coming-of-age ceremony for Honolulu, which had been steadily building its street cred in skate culture throughout the 1980s. The game-changing Y-Ramp and its world-class riders, including local pros Johnee Kop and Bo Ikeda, affirmed the Islands’ role in the progression of radical skating.

One key constant between the original contest and this year’s replica was the prominent presence of an artist-skater from Hawai‘i Kai named Mark Oblow—or “Moblow”—the only person to judge both events. Dressed in fashionable white pants and the same orange aloha shirt he wore at the 1989 contest, Oblow got his chance to sample the reincarnated ramp after Payne and Sandridge’s opening runs, which ended disturbingly with Sandridge flying off the ramp and landing headfirst in the sand. (He shook it off.) Undaunted, Oblow, now an influential documenter of skating’s literal and figurative ups and downs through his photographs and mixed-media art, rolled straight for the sharp spine down the middle of the ramp and deftly locked his front axle on the sliver of coping at its apex, then pivoted his weight to the opposite side.

In that moment, he says, he dropped back into 1989. “It was the first time I had ever seen a spine, let alone skated one,” Oblow says of the Blaisdell Y-Ramp. One of the pros showed him how to navigate the feature, and the lesson was then seared into his memory as, from his ramp-side judge’s seat, he watched every kind of spine trick possible being performed by a full pantheon of skate gods.

Old school meets new: Third-generation hellman Greyson Fletcher goes big over the sharp spine running across the center of the ramp. A mix of current stars and legendary skaters from the 1980s and 1990s turned out for the event.

“I can still see them all, picture-perfect,” Oblow says. There was Hosoi, skate-boarding’s glam rock star in Spandex shorts, stalling his board on the rim of the ramp and shouting along to the chorus of “Wild Thing.” Santa Cruz Skateboards pro Jeff Phillips performed a dramatic leap off one leg, called a “boneless,” across the open chasm in the ramp’s bifurcated wall. A gangly teenager named Tony Hawk showed hints of the brilliance that would later make him the most famous skater ever. And finally there was the trick that sent the packed arena roaring: The Gonz’ mind-melting no-grab jump over the channel. That last moment is indelible in the annals of skate history, thanks in part to footage captured by director Jeff DePonte for a televised broadcast of the contest.

“I think he was probably very afraid that he had just broken his leg,” DePonte says, looking back on his footage of Gonzales’ first attempt, in which he fell short and clipped his legs on the edge of the landing ramp. “I can tell you that if my shin hit the ramp like that, I would not be getting up to take another pass.” But Gonz did. On his second attempt, he pumped hard into the launch and scooped his board high into the air. “People got up out of their seats, because they knew it was coming,” DePonte says. “He’s gonna go for it no matter what.” The film captures the astounding moment as Gonzales clears the edge and slaps his board down on the landing ramp with a vengeance. As he tears across the ramp’s flat bottom, the camera catches him mouthing a fierce “Yeah!”

Many of the skaters who competed in the original event returned three decades later for the revival, including (from left to right) Mark Gonzales, Eric Dressen, Christian Hosoi and local street innovator Jef Hartsel.

The 1989 Y-Ramp festivities capped off an epic decade of skateboarding in Hawai‘i that, in those days before YouTube and social media, had largely gone un-documented—that is, until a young Mark Oblow picked up a point-and-shoot film camera. Oblow’s privileged vantage point hails back to his teenage friendship with Johnee Kop, the first pro skater to emerge out of the Islands. Kop introduced young Oblow to Hosoi, “and that’s really how I think it all started for me,” he says.

Throughout the early ’80s, Hosoi ditched California on a monthly basis for the Islands’ surf breaks and skateable backyard pools. “People thought he lived in Hawai‘i,” Oblow says. “He would always rent a white Lincoln Town Car, and people thought that was his car. They’d be like, ‘Where does Christian keep his car when he’s gone?’”

Where Hosoi went, others wanted to be. As skaters arrived en masse, they would seek out Oblow and his brother Scott for the scoops on everything from where to find empty pools to skate to a place to crash for
 the night. “Skateboarding was such a small thing then, and all skateboarders loved and embraced all other skateboarders,” Oblow recalls, his raw teen stoke still palpable today. “My mom would cook breakfast and there would be all these top pros at my house in the morning. It was like, ‘I’m hanging out with all my heroes, they’re all cruising at my house, and they’re all humble and rad!’”

The grafitti painted on the ramp for the original contest was recreated for the 2018 reboot. Here, Honolulu skater Heimana Reynolds, a recent X-Games contestant, gets a bird’s-eye view of the artwork.

One of the least known among Oblow’s dream team of crashers arguably had the most impact on the budding skate artist. By the late ’80s, Kevin Thatcher had transitioned from pro skater to photography editor of Thrasher. “He came over and did the first Hawai‘i article for Thrasher,” Oblow says. “I met him then and he just inspired me to shoot.” Thatcher allowed Oblow to watch over his shoulder as he documented Hawai‘i skate terrain found nowhere else in the world, like the big, wavy drainage ditch in East Honolulu’s Niu valley that came to be known as Wallows.

The wave of Island skate tourism crested with the watershed 1987 film The Search for Animal Chin, directed by original Dogtown Z-Boy Stacy Peralta, which was among the first skate flicks to have an actual plot. Memorably, and rather unfortunately, that plot featured a tacky Orientalist quest for skateboarding’s mythical founder, an old Chinese man named Won Ton “Animal” Chin, who had inexplicably gone missing. The skate-heavy search, led by the elite Powell-Peralta Skateboards team, the Bones Brigade, began at Wallows.

At the age of 49, Mark Gonzales, a finalist in the original contest, successfully repeated his dramatic 1989 leap across the gap in the Y-Ramp—one of a multitude of tributes to the original event.

VHS sales of the film caught fire, whisking Hawai‘i’s skate spots beyond the domain of elite pros and into the living-room fantasies of teenage riders across the country. But for 16-year-old Moblow, it was all real. After Mrs. Oblow’s breakfasts, the amorphous posse of skaters could carve downhill along the steep banks of a nearby ditch known as Off the Walls and then cut through a hole in the fence and across the Hawaii Kai Golf Course straight to Sandy Beach for a day of skimboarding. With booming skate-wear manufacturers starting to hand out serious sponsorships, eventually Oblow, who had started out surfing, got picked up by California-based Vision Street Wear for his skating.

In the climax of The Search for Animal Chin, the Bones Brigade ends up stumbling upon an enormous abandoned half-pipe in the California desert. That fantasy ramp was built by none other than Tim Payne and his punnily named Team Pain Skate Parks, and it was the first ever to include a spine. Part way through the Brigade’s high-flying session, pro Tommy Guerrero discovers that one piece of the spine can be removed, creating a channel. Two years later, the contest at the Blaisdell gave Payne a chance to reconfigure these innovations to use the spine as a setup for skaters to connect a series of tricks before clearing the even larger channel in the vert wall. The Y-Ramp was born.

The 1989 Y-Ramp contest was something of a coming-of-age ceremony for Honolulu skateboarding. Throughout the ’80s, local skaters like Johnee Kop (seen here) had been building cred at spots like Wallows, a steep, wavy East Honolulu drainage ditch.

Those same features were once again on glorious display at this year’s Waikīkī sequel. “It was so fun seeing everyone there,” Oblow says, “from guys I grew up skating with to the young generation.” Hosoi once again danced on the edge of the ramp before dropping in and blasting high into the air. Cab, now sporting a thick silver beard, slid his board smoothly across the spine just like in ’89. Inspired by the remarkably intact skills of their elders, upstart talents soon converged upon the Sphinx, occasionally colliding and forcing each other into the sand.

A local prodigy, 11-year-old Cyprus Blanco, did a 360 air over the spine and snagged the day’s best trick award, beating out contenders several times his age. Blanco’s skate buddy Heimana Reynolds, a recent X-Games competitor, was in top form too, launching and flipping his board high into the sunny sky. But it was the stylish and consistent aerial spinning of California’s Roman Pabich that led Oblow and his fellow judges to give him the day’s overall win.

And then there was The Gonz. Sparked as ever at age 49, he zipped around the ramp wearing white pants hand-painted with colorful stars and even dragged the emcee’s microphone along the coping to share the grinding sound with the crowd. As their energy mounted, Gonz went ballistic. Not only did he reproduce his own 1989 flying jump across the gap, but he actually one-upped himself, channeling his momentum into a tribute to the late Jeff Phillips by launching a fully extended replica of Phillips’ classic “boneless” over the gap. A shot of the insane move landed on the cover of Thrasher, and in the background the bleachers hold a who’s who of Hawai‘i skateboarding—its veterans, its new blood, its artists—all joined together in celebration of the Islands’ special place in the history of skate. In all, quite a bewildering sight for the smattering of mystified tourists who had wandered down from their hotel rooms to see what had become of that painted wooden Sphinx on the beach. HH