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Jeff Grosso: The life and death of skateboarding’s soul By Jack Harris
Los Angeles Times Exclusive
March 4, 2021 4 AM PT
Jeff Grosso’s first skateboard wasn’t much.
It was a hand-me-down miniature-sized banana board he got from his mom’s boss when he was 8 years old. Even for 1977, it was antiquated, with rickety old clay wheels and worn-out bearings. Grosso barely knew how to stand on the thing, struggling to keep his balance without toppling to the ground.
But for a curious boy whose childhood home was next to a steep hill, there was an instant connection. He would sit on his back or lie flat on his stomach and let gravity take over. Every time he bombed down the street, he fell more in love with the feeling.
“Initially, it was the rush of going down a hill, and the wind in your hair,” Grosso once said. “Poetic nonsense.”
The skateboarding world looks much different now than it did then. Its ever-increasing popularity is pulling the fundamentally subversive sport into the mainstream. Formerly relegated to back alleys and sparse concrete parks, it is now set to debut on the Olympic stage during this summer’s Tokyo Games.
But somewhere at its core, the lust for that poetic nonsense remains.
No one understood it quite like Grosso.
“He was the gatekeeper to why skateboarding was cool,” said skateboarding legend Tony Hawk.
Grosso looked an unlikely figure for such a role. He didn’t have a long pro career, flaming out at the end of the 1980s, hardly spanning the decade. He battled drug addiction and suicidal depression. By his late 20s, it seemed like his life had bottomed out.
But then he rebounded, embodying the resiliency that has defined the entire history of his sport.
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Grosso became an ambassador, speaking for skateboarding’s soul through his beloved “Loveletters to Skateboarding” YouTube show. He was a guardian and a helping hand to skateboarding’s newest generation.
In many ways, he was like a north star, his effervescent personality and endearing pertinacity emitting a guiding light through the sport’s most transitional times.
And when he died unexpectedly last March of an accidental drug overdose, it left a void the skateboarding world is still trying to fill.
To best understand skateboarding — its counter-culture roots, its rise to the Olympics, its helter-skelter tale of competing styles, clashing customs and self-sabotaging plot twists — it’s best to understand someone like Jeff Grosso.
Complicated. Flawed. But an authentic source of joy to the end.
“It’s a total rush. It’s the feeling that when you go out there with your board, it’s a no-hero type of thing. And you either accomplish something or you don’t.” — Jeff Grosso, to the St. Louis Dispatch in 1986.
The rarest sight in skateboarding might be a frown.
Even after a failed trick or nasty wipeout, most skaters are wired to smile, laugh, shake off the dust, and climb back on their boards.
That carefree disposition is what initially captured Grosso’s interest. A stubborn and expressive freckle-faced kid born in Glendale in 1968, he felt like an outcast from a young age. He liked to draw, read “Lord of the Rings” and listen to punk rock. He picked contrarian arguments during conversations simply to spark a debate. And he moved around a lot as a kid: from the hillside house in Eagle Rock, to Las Vegas for a year with his mom, and then to Arcadia for the start of fifth grade.
Though he was naturally athletic, he found the structured pressure of team sports arbitrary and suffocating.
Only when he was on a skateboard did Grosso truly feel free.
“You have this culture of kids that need that,” said his mother, Rae Williams. “They need to go and do this and be creative and come up with new tricks and try different things.”
Like Grosso, skateboarding’s subversive identity was almost baked in from the start.
Originally popularized in the early 1960s by Southern California surfing companies innovating dryland alternatives, the sport was quickly tagged with a dangerous reputation. In 1965, the California Medical Assn. called it “a new medical menace.” Cities across the country banned the activity on public sidewalks and streets. It has teetered on the fringes of mainstream society ever since.
Its popularity spiked in the early ‘70s. Improvements to the board and wheels gave birth to more ambitious vertical skating, a style defined by gravity-defying aerial tricks off half-pipes and vertical ramps. A string of Southern California droughts turned empty swimming pools into skating bowls. Rapid construction of skate parks nationwide soon followed, bringing millions of kids to the sport.
It wouldn’t last.
The newly opened parks soon faltered under liability issues and financial distress, and the young demographic of riders once fueling the boom grew up and moved on. By the time Grosso discovered the sport at the end of the ‘70s, only a small community of self-willed skaters remained.
“Skateboarders were very rare at that time,” said Grosso’s childhood friend Eric Nash, the only other kid at their Camino Grove Elementary School who matched Grosso’s passion for the sport. “Jeff enjoyed that rebel spirit. I think that’s who he was.”
Grosso and Nash spent almost every weekend at one of the few Southland skate parks that were left. Grosso was a perfectionist — at home he was constantly rearranging the furniture in his bedroom — and practiced for hours to perfect a trick. Skate City in Whittier became their home base, though sometimes they snuck away to more secluded spots — a cement ditch behind a church in Glendale, an empty washway nicknamed the “V bowl” in Irwindale.
One of their friends, future pro skater Lance Mountain, had a ramp in the backyard of his Alhambra home where the group would spend hours together honing their technique and embracing a recalcitrant culture few others could comprehend.
“We were a bunch of nerds, we were weirdos, we were social outcasts,” Grosso said in a 2015 episode of his “Loveletters” series. “We were the people that nobody wanted to be, doing things that nobody wanted to, and that nobody understood. … We were the freaks. That’s how you rolled. That’s how it was. That’s what drew us to skateboarding.”
“The little wooden toy is a kiss and a curse. It’s everything. It’s the best thing that ever happened to me and the worst thing that ever happened to me, all rolled up into one.” — Jeff Grosso, to Juice Magazine in 2006.
Like any good parent, Williams tried to get her son to think about his future as he went through grade school. Skateboarding, she told him, “is fun and can be a pastime, but you can’t make a career out of it.”
Reliving the memory during an interview, Williams stopped herself and laughed.
“Boy, were we wrong.”
Instead, as Grosso went through his teenage years in the mid-1980s, the sport became cool again.
Vertical skateboarding benefitted from the formation of the popular National Skateboarding Assn. contest circuit. Skateboarding scenes in hit films such as “Back to the Future,” “Police Academy 4” and “Thrashin’” reintroduced the sport to a broader audience.
Now top skateboarders had the opportunity to make six-figure incomes through sponsorships and competitive earnings. The timing was perfect for Grosso, who blossomed into a top amateur before dropping out of high school to turn pro in 1986. He was 17.
“Jeff and I had a similar trajectory, in that we both fell in love with skating when it was absolutely at its least popular cycle,” said Hawk, one of the defining skateboarders of the late 1980s. “We loved it because we loved the crew, the misfit aspect, the rebellious aspect. Our whole thing was, we don’t want to fit in, we want to do our own thing. Then suddenly, we found ourselves with some success and fame.”
Competitively, Grosso didn’t match the likes of Hawk, Christian Hosoi and other preeminent skaters of that era. But culturally, his stature was nearly unmatched.
He had many of the bestselling board designs and starred in some of the period’s most prominent skateboarding videos that played an outsized role in promoting skateboarders and their sponsors to fans nationwide.
Grosso’s relatable skating style made him popular, mastering fundamental tricks any amateur skater could mimic on their own.
It was his playfully devious personality, though, that gave him a cult following. In one particularly memorable video, Grosso shaved off his eyebrows before describing the life of a professional skateboarder: “Lounge around all day, do absolutely nothing, until it’s time to ride your wooden toy.”
Later in life, Grosso admitted there were signs of trouble brewing behind that facade. The kid who used to get “tripped out” by seeing older skaters smoke Marlboro Reds was now “smoking pot and drinking and living the rock star lifestyle that I’d come to covet,” he later said. “I started down that path.”
To the skateboarding public, however, his persona was well-received.
“Grosso was the guy you could actually aspire to be like,” said Coan “Buddy” Nichols, a childhood fan of Grosso’s who was later a producer of the “Loveletters” series. “He was loud and crazy, because he was partying, having a good time. That’s a classic thing in skating, to mix the athleticism with real life.”
But like a flickering candle at the end of its wick, those golden days began to fade.
Even though Grosso’s generation revived skateboarding’s popularity, skate parks and vert ramps were still rare in most parts of the country. The new skaters they’d inspired gravitated toward a different style, riding off urban obstacles such as staircases, park benches and handrails.
The new discipline became known as street skating, and by the early 1990s it began to consume the sport. Suddenly, it was no longer cool to be a vert star such as Grosso or Hawk. Contests that once drew thousands began to fold and the sport’s media attention was redirected toward its newest trend.
Worse than that, many skaters felt as though their whole lifestyle had been discarded. Scenes in skating videos featuring their old aerial tricks were skipped over so often that fast-forwarding became known as the “vert button” on the remote. Half-pipes and vertical ramps became so rare that the entire discipline was in danger of extinction.
“We were almost akin to boyband fame,” Hawk said. “And it was all washed away within a year.”
“I didn’t think it was ever going to end. I had no concept of what was really going on. I wasn’t making plans for the future. I’m a high school dropout. It was like, ‘I’m a pro skateboarder, and the party is never going to end. I’m indestructible’ … I was wrong.” — Jeff Grosso, to Juice Magazine in 2006.
Grosso woke up one morning in the mid ‘90s and walked to a mirror. He saw that he was still alive. Part of him wished that he wasn’t.
Staring into the reflection, he no longer recognized himself. Only a few years removed from the height of his pro career, his life was spiraling into an abyss.
Even after vert skating’s demise, Grosso had tried to stay relevant in the sport. He sold boards for an upstart skating company called Black Label run by John Lucero, another childhood friend and former pro. He traveled to the few slimmed-down competitions that remained. He clung to whatever notoriety he had left.
But as the ‘90s progressed, and the ever-more fragmented skateboarding community floundered during an economic recession, he struggled to reckon with his new reality. He tried to find ways to escape it.
He had a heavy drinking problem, then began using methamphetamine and heroin. His income couldn’t always fully fund his habit, so he sometimes stole VCRs and TVs from friends to sell at pawn shops.
He tried rationalizing his choices, convincing himself that as long as he could keep skateboarding — even if it no longer served as his primary occupation — he was fine.
“I just sort of floated around,” he said. “When you’re hanging around with the kind of people I was, it’s pretty easy. … In one town you’re on speed, and then the next town it’s booze, and the next one it’s heroin. You just keep shuffling the problems around.”
His addictions, however, eventually wore him down.
One night, as he later told Thrasher magazine in 2007, he intentionally tried to overdose at a friend’s house, only to wake up the next day and look into that mirror, realizing it hadn’t worked.
Three other times, he was rushed to the hospital with no vital signs after overdosing, later telling Transworld Skateboarding magazine that one of the incidents had been another intentional attempt.
“When you’re lost in heroin, and you haven’t reached any sort of bottom, you just can’t see out of it,” Grosso said in 2003. “You have to get an extreme amount of pain before you can accept anybody else’s help … It’s a real rough road, man. Trying to get your life back from being a real scumf--- is a really hard thing to do.”
His short-lived pro career wasn’t the only cause for his struggles — “It’s not any one thing, it’s the addiction that’s the problem” his mother said — but it robbed him of the most central element to his identity. His story wasn’t unique at a time when many notable skaters from his era went to jail or battled substance abuse.
“These guys, they were celebrated while they’re still developing as teenagers, everyone telling them they’re God’s gift to skateboarding,” said Mackenzie Eisenhour, a longtime writer for Transworld Skateboarding. “And then the industry completely shifted. All of a sudden, you’re disposable.”
It would be like the basketball world renouncing Michael Jordan, deciding to no longer buy his shoes, and declaring dunking a thing of the past. The painful irony: Vert skating’s demise was caused by the very same rebellious, subversive dynamics that drew Grosso and his peers to the sport in the first place.
“Skateboarding is an anti-hero culture,” Eisenhour said. “So once the culture deems you the hero, it’s just waiting to rebel against you.”
“You know what I really regret? I don’t regret partying. I don’t regret becoming an addict and s---ing my life away. I regret taking my skateboard for granted. I wasted years and years running around doing bulls--- when I could’ve been riding.” — Jeff Grosso, to King Skateboard Magazine in 2016.
For more than two decades, Nichols and Rick Charnoski, his partner at Six Stair Studio, have traveled the world documenting skateboarding and producing films about its culture.
One thing they’ve learned: “Skateboarding has these two directions,” Nichols said. “The sport that some people want it to be — mostly to make money off of it, honestly — and then the lifestyle, everything else around it.”
Can the sport be commercially successful and culturally authentic? Can it enter the mainstream without being co-opted? Can it keep an edge without excluding everything and everyone that came before it?
There’s a reason that different styles have competed for its direction, its customs, its icons. It was no surprise that when skateboarding was added in 2015 to the Tokyo Games — one of several action sports the Olympics has introduced in hopes of attracting younger audiences — there was a rebellion against it. Skateboarders started an online petition, which drew 7,500 signatures, asking the International Olympic Committee to reverse its decision and remove the sport from its lineup.