30 Most Influential Skateboarders of All Time

From the Z-Boys of Dogtown to the corporate-driven stars of the X Games, these are the skateboarders that forever changed the sport.

30 Most Influential Skateboarders of All Time

Skateboarding has come a long way since American kids in the 1950s affixed roller skate wheels to fruit crates salvaged from the back of grocery stores. The modern form represents many nationalities, colors, cultures and sexes. It’s the embodiment of diversity and democracy. Anyone can play, and skaters make their own rules. All you need to do is step out your front door and push.

That’s what every member of this carefully cultivated collection has in common. They started on the driveway, or the sidewalk, or the street in front of their home. Skateboarder, artist, author and iconoclast Craig Stecyk summed it up perfectly: “Two-hundred years of American technology unwittingly created a massive cement playground of unlimited potential. But it was the minds of 11-year-olds that could see that potential.”

Some of these influential skateboarders found the height of wealth and fame. For others, life became a series of hard falls. But all attained a measure of greatness and influence they never could have imagined.

30. Andy Anderson

Born: April 13, 1996

Decade he helped define: 2010s-2020s

Notable achievements: Canadian Nationals Men’s Park Finals champion (2020), World Skate London Men’s Open Street (4th/2019), Grand Prix Beroun Pro (2nd/2018), Flowgrind International – Pro (2nd/2018), Zumiez Best Foot Forward (2nd/2016)

Key videos: Andy Anderson’s #DreamTrick, Seen Him, Andy Anderson: a Short Skate Film, The Most Creative Skater at Venice Skatepark, The Most Creative Skater in the World?, Powell Peralta Skateboard Stories - Andy Anderson

Find on Instagram: @authenticandyanderson

Bottom Line: Andy Anderson

One of the bedrock principles in skating is that specialization doesn’t cut it. Skaters must handle all terrain. No one embodies that more than a slight, unfailingly polite young Canadian who seamlessly links street, freestyle and vert skating into a discipline that’s his alone. It’s mesmerizing to witness, and it’s put Anderson on the short list of skaters that other skaters openly envy.

His parents introduced him to the sport at age 2 when they brought him to Vancouver’s Griffith Bowl. He didn’t skate it — “I think it was more of a subconscious thing,” he said — but he was rolling with purpose by 4, ollieing and flying out of bowls at 8, then securing a coveted sponsorship with Powell-Peralta. “I played baseball and all that. I played piano,” Anderson said. “It all stopped for skateboarding.”

He’s known for wearing a helmet, a safety stance that has created some separation from the vast majority of his contemporaries, for whom any protection is dismissed. A black mark? Hardly. Simply further evidence that, like his skating, he does it his way.

29. Lyn-Z Adams Hawkins

Born: Sept. 21, 1989

Decade she helped define: 2010s

Notable achievements: Women’s Vert World Champion (2009, 2019), 8-time X Games medalist (3 gold, 4 silver, 1 bronze), first woman to land a 540 McTwist

Key videos: Going Nowhere Faster, Lyn-Z Adams Hawkins Vans Triple Crown 2004

Find on Instagram: @lynzskate

Bottom Line: Lyn-Z Adams Hawkins

The Encinitas YMCA has been a cradle for great skateboarders over the years, and Adams Hawkins is among its most distinguished alumni. She began skating there at age 6, adding it to a list of competitive sports that included surfing, soccer, baseball, basketball and gymnastics.

She’s broken new ground for women skaters. Adams Hawkins is the first female to land a 540 McTwist, achieved during the 2009 "Quiksilver Tony Hawk Show” in Paris. She’s the only woman to have skated the DC Mega Ramp and the Giganto Ramp, the latter of which features a 40-foot gap (she clears it with ease and style). Her husband, Travis Pastrana, is a multi-discipline motorsports competitor, with X Games gold medals in supercross, motocross, freestyle motocross and rally racing. “She likes to fly,” said Pastrana, “and that’s why we ended up together.”

28. Alan Gelfand

Born: Jan. 1, 1963

Decade he helped define: 1970s-1980s

Notable achievements: South Florida Skateboard Championships (1st / 1976), 1979 Vans Marina Pro-Am Skateboard Competition – Men’s Pro champion, 1979 Hester Series 3 – Amateur Open Pool & Halfpipe champion, 1980 Big O Pro-Am (2nd) and Highest Air (1st)

Key videos: Bones Brigade: An Autobiography Movie CLIP – Ollie Air, World’s First Ever Skateboard Ollie

Find on Instagram: @alanolliegelfand

Bottom Line: Alan Gelfand

His career was not particularly lengthy. And his contest victories were few. So, what’s he doing on this elite list? He invented the ollie, the trick that influences every aspect of modern skating. And … wait for it: He did it on vertical! Simply, it was the skateboarding equivalent of the moment when God and man touch fingers on the ceiling of the Sistine Chapel.

Gelfand was a relatively unknown Florida skater at a time when there was little coverage of anything outside California. Stacy Peralta, a first-generation Dogtown skater and the man behind the Bones Brigade team, witnessed the skater known as “Ollie” performing frontside aerials no-handed. After he’d reconciled his initial disbelief, he wasted no time recruiting Gelfand as the first rider for the Powell-Peralta company team. “The ollie is, without doubt, the most revolutionary trick of the 20th century," Peralta said years later.

Currently, more than 15 ollie variations exist. Both the Oxford English Dictionary and the Merriam-Webster Dictionary credit Gelfand under the entry of “ollie.”

27. Mike Vallely

Born: June 29, 1970

Decade he helped define: 1980s-2000s

Notable achievements: Thrasher magazine cover (1986), X Games Street: 4th (1995), X Games Street: 7th (2003), appearances in The Hangover, The Hangover Part III, Paul Blart: Mall Cop

Key videos: Public Domain, Label Kills,The Search for Animal Chin, Mike Vallely | The Nine Club with Chris Roberts

Find on Instagram: @mikevallely

Bottom Line: Mike Vallely

Vallely was discovered by three skating legends — Neil Blender, Lance Mountain and Stacy Peralta — as a kid spectator rolling in the parking lot of an East Coast park hosting the trio for a pro competition. Mountain gave him a board to replace his beat-up model, and following an impromptu tryout, Peralta offered him an amateur sponsorship with his company, Powell-Peralta.

Plucked from obscurity, he turned pro in 1987, and Powell-Peralta released his signature model board a year later. His specialty was inventive street skating, making the most of minimalist terrain — handplants off parking bumps, board slides on curbs, climbing walls with no transition. It was a time when street-skating was gaining momentum, and Vallely led the charge.

After leaving Powell-Peralta, he formed numerous successful partnerships. His World Industries Barnyard deck is credited with starting a revolution in deck shape, popularizing the popsicle design that’s standard in all forms of skating today.

26. Eric Koston

Born: April 29, 1975

Decade he helped define: 2000s-2020s

Notable achievements: Skateboarder of the Year Thrasher magazine (1996, 2001), Summer X Games: Gold (2000, 2002-3), X Games Global (2005), 1st: Dew Action Sports Tour – Park and Street (2005), 1st: Van’s Downtown Showdown (2005), 1st: West 49 Canadian Open (2005), 1st: Tampa Pro Street (2005)

Key videos: Yeah, Right!,Epicly Later’d,Eric Koston: One Obsession, This Is Eric Koston,Goldfish, Fully Flared, Eric Koston: The State of Skateboarding | X Games, Falling Down

Find on Instagram: @erickoston

Bottom Line: Eric Koston

Koston was born in Thailand to an American Air Force father and a Thai mother. After moving to San Bernardino, California, he picked up a board at age 11 and was soon represented by the industry’s leading brands: H-Street, 101 (an arm of World Industries overseen by Natas Kaupas), Girl, shoe sponsors Lakai and Nike SB, and Oakley eyewear.

He’s a proponent of the power of visualization, which led him to deploy signature moves such as the “K Grind” and the “Fandangle.” His natural stance is goofy foot, but he’s known for his ability to skate switch-stance, one of many techniques he polished at Lockwood Elementary in Los Angeles, famed for its street skating history.

He also has a flair for the dramatic, never more evident than when he wore a Lakers jersey to the X Games in Philadelphia after L.A. defeated the 76ers for the 2001 NBA title. Boos rained down until he nailed a move called a Back Noseblunt en route to a Silver medal.

25. Andrew Reynolds

Born: June 6, 1978

Decade he helped define: 1990s-2000s

Notable achievements: Skateboarder of the Year Thrasher magazine (2000), ranked 10th on “Transworld Skateboarding’s” list of Most Influential Skateboarders, Maloof Money Cup – 1st place (2011)

Key videos: Andrew Reynolds – Life on Video: Episode 1, The End, Stay Gold, Andrew Reynolds | The Nine Club with Chris Roberts, Vice: Skateboarding with Andrew Reynolds, Andrew Reynolds and the Madness, Feasters, The End, In Bloom, This is Skateboarding

Find on Instagram: @andrewreynolds

Bottom Line: Andrew Reynolds

Reynolds started his career in the Florida Amateur Skateboard League at age 9, quickly gaining sponsorship from the legendary surf/skate brand G&S. He moved to Huntington Beach, California, to advance his career following high school and quickly caught the eye of the great Tony Hawk, who was leaving Powell-Peralta to launch a new team.

Hawk’s Birdhouse team selected Reynolds as one of two amateurs, and with it, a new chapter in skateboarding history began. Known as “The Boss,” Reynolds has demonstrated a dedication to his craft that’s unique, even among his peers. "I don't know how he does it. I don't know how he jumps down the stuff he jumps down, year after year still be like ... I don't know — to me, it's shocking,” said pro skateboarding peer Ed Templeton.

After years living the fast-lane lifestyle of a young, well-compensated skater, Reynolds committed to sobriety, which opened the door to starting a company, fatherhood and a wealth of other life opportunities. He considers Mark Gonzales the most influential skater of all time. His signature trick is the Frontside Flip.

24. Shogo Kubo

Born: Sept. 19, 1959

Died: June 4, 2014

Decade he helped define: 1970s

Notable achievements: Skateboarding Hall of Fame (2017), 1978 Hester Series at Newark Skatepark – 9th in pool

Key videos: Dogtown and Z-Boys,Skateboard Kings,Skateboarding Hall of Fame 2017 – Shogo Kubo Acceptance Speech by Shota Kubo, Skateboarding Hall of Fame Jeff Ho inducting Shogo Kubo into the Skate Hall of Fame

Find on Instagram: @kuboshota (featuring past photos of him but is mainly his son’s skateboarding-focused account)

Bottom Line: Shogo Kubo

A member of the original Z-Boys, Kubo moved to West Los Angeles from Japan as a child. He spoke no English and was ostracized and mocked in elementary school. But he forged a friendship with fellow Dogtown local Jay Adams in judo class and eventually bought a surfboard from him, forging a lifetime bond.

Kubo was the first Asian-American skateboarder to appear in the major magazines and garner sponsorship, opening doors for future superstars Christian Hosoi, Lonnie Hiramoto, Lester Kasai and Jerry Hsu. When the Zephyr team dominated the 1975 Bahne-Cadillac Del Mar Nationals, the sport was changed forever, and Kubo was a driving force in that revolution. His surf-influenced carving style and slashing extended frontside laybacks on vertical were his signature. And the ever-present headband, of course.

He designed a sneaker for Nike in 2007, the Nike SB "Shogo" Blazers in tribute to the suede, high-top basketball Nikes he was photographed in decades ago, when Nike was a little-known brand and the only manufacturer associated with the sport was Vans. Much-heralded Mark Gonzales lists Kubo as one of his favorite skaters.

23. Pedro Barros

Born: March 15, 1995

Decade he helped define: 2010s-2020s

Notable achievements: World Skateboarding Championship: Gold (2018), Silver (2016-17); Summer X Games: Gold (2009-16), Silver (2011, 2013, 2015), Bronze (2009).

Key videos: Silver Era, Pedro’s Bigger Picture, Take It Back, Vans Park Series 2018 Rider Profile: Pedro Barros

Find on Instagram: @pedrobarrossk8

Bottom Line: Pedro Barros

The inventive aerial talent has made the X Games his personal playground over the better part of the last decade. He burst onto the scene with a gold medal in the 2008 X Games Vert amateur event, following it up a year later with a bronze.

His Vans Park Series record is matched by few. And while he’s highly regarded for his pool skating, his dedication to style has produced an impressive street resume. Barros began skating on a backyard ramp built by his father in his hometown in Brazil, then pursued a career in U.S. contest skating despite the challenges of being an outsider.

“At 15 or so, he started skating events,” said veteran pro Omar Hassan. “His dad would take him out to contests. He would sleep on floors. It wasn’t like he had this groomed upbringing like Americans do. He was definitely grass roots.”

22. Stevie Williams

Born: Dec. 17, 1979

Decade he helped define: 1990s-2010s

Notable achievements: Ranked 27th on Transworld Skateboarding’s list of Most Influential Skateboarders

Key videos: The DC Video – Stevie Williams,Being Stevie Williams Extended Cut World of X Games, Stevie Williams, The Reason, Tony Hawk’s Project 8 Stevie Williams Pro Footage,Fresh ‘til Death,Da Playground,Parental Advisory

Find on Instagram:@steviewilliams

Bottom Line: Stevie Williams

Not many people have completed the transition from homeless teen to skateboard industry mega-mogul. In fact, there might be just one. As one of the pioneers of inner-city skateboarding (primarily at Philadelphia’s LOVE Park), Williams got his first board at 11, garnered sponsorship at 12 and, by 14, set out for the skating mecca of California by hitchhiking across the country. He slept on couches, relying largely on the brotherhood of the local skate community.

It’s a long way from there to a personal invite to visit Michael Jackson at the pop star’s Neverland Ranch, but for Williams it was just another day in the life. Jackson wasn’t a skater, but his nephews identified Williams and Chad Muska as their two favorites, bringing music and skateboarding royalty together for a day that began with Jackson’s carrying an open umbrella indoors.

Williams took a seemingly negative label, applied his original East Coast skating posse — “dirty ghetto kids” — and transformed it into one the industry’s most successful brands in DGK. In addition to skateboard decks, he inked a groundbreaking partnership with Reebok to create skate shoes and a clothing line.

21. Geoff Rowley

Born: June 6, 1976

Decade he helped define: 1990s-2010s

Notable achievements: Skateboarder of the Year Thrasher magazine (2000), ranked 26th on Transworld Skateboarding’s list of Most Influential Skateboarders, inventor of the trick Rowley-Darkside

Key videos: The Dreams of Children,Vans Propeller,Pleased to Meet You Tour (2005),Really Sorry, The Global Assault, Sorry, Take It Back

Find on Instagram: @geoffrowley

Bottom Line: Geoff Rowley

The super-smooth and dangerously adventurous Rowley didn’t grow up in a cradle of skateboarding. Finding skate gear in the British city of Liverpool was a challenge. In fact, the only skate shop in town was actually a record store with a little skate section in the back. After establishing himself in the U.K., he moved to Huntington Beach, California, in 1994. Two weeks after arriving on the West Coast — little money, no car, only a few skateboards to his name — he landed on the cover of TransWorld Skateboarding — executing a 360 Flip on a rail at Oceanside High School in North San Diego.

Soon he was blazing a new trail with guys like Rune Glifberg, Ed Templeton and Tom Penny. He attacked the biggest challenges and absorbed some of the hardest falls (see: Geoff Rowley Never Gives Up on YouTube). Rowley is immortalized outside the L.A. Convention Center with a bronze, life-sized statue of him pulling an iconic trick dating back to 1999. Another signature image was captured in 2008 when he leaped a 15-foot gap between a pair of shipping container stacks (measured at 52 feet in height) at the port of Long Beach, California.

20. John Cardiel

Born: Dec. 14, 1973

Decade he helped define: 1990s

Notable achievements: Skater of the Year Thrasher magazine (1992), ranked 11th on Transworld Skateboarding’s list of Most Influential Skateboarders, ranked among Top 25 Tahoe Snowboarders by Tahoe Quarterly (2020).

Key videos: John Cardiel, Sight Unseen, 30th Anniversary Interview: John Cardiel – TransWorld Skateboarding, Epicly Later’d, Cash Money Vagrant, Classics – John Cardiel S.O.T.Y.

Find on Instagram: @johncardiel

Bottom Line: John Cardiel

Cardiel spent much of his childhood in Half Moon Bay, California, just down the road from the massive, world-famous Mavericks surf break. Perhaps it’s no surprise his skating represents extreme kinetic energy and a fearless mentality. He approaches everything at full speed. “Hard-charging” doesn’t begin to describe it. His style is immediately recognizable.

“I just want to say a few things about John Cardiel,” said Mark Gonzales, a Top 5 choice on anyone’s all-time list of skateboarders. “First off, he’s an original. His style, I mean there’s not too many people that skate like him. The way he skates is amazing. He’ll skate so fast. It seems like the faster he goes the more control he has. Which is, you know, unexplainable.”

Cardiel counts Gonzales and Christian Hosoi among his early influences, with Santa Cruz standouts Raven Tershay and Emmanuel Guzman among his current favorites. Cardiel is known for his exploits on bikes and is an elite-level snowboarder. He’s also heralded for his miraculous return from a spinal cord injury, a freak accident with a trailer in Australia. He spent six months in rehab and was released in a wheelchair with serious questions if he’d walk again. He went on to make a full recovery.

19. Nyjah Huston

Born: Nov. 30, 1994

Decade he helped define: 2010s-2020s

Notable achievements: World Skateboarding Champion – Street (2014, 2017-19). X-Games gold medalist (2011-16, 2018-19), Best Male Action Sports Athlete – ESPYs (2013-14)

Key videos: Elementality, Rise & Shine, The Motivation,OMFG, Nyjah Hyston: Real Street Best Trick 2020 | World X Games

Find on Instagram: @nyjah

Bottom Line: Nyjah Huston

There are many ways to measure a skater’s impact andlegacy. Huston’s is one of high-profile victories and massive earnings. And his ability to annihilate a street course with a flowing, athletic routine. Since storming the scene and electrifying the X Games at age 11, he’s become one of the most successful commercial skateboarders.

His contest winnings are well into the tens of millions. His triumph at the Street World Championship Final of the 2015 Kimberley Diamond Cup in South Africa earned him the largest single-event prize in the sport — $100,000. Sponsorship that began at age 7 from Element Skateboards has transitioned into major relationships with global brands such as Nike and Monster Energy.

In 2020, he won the inaugural X Games Real Street Best Trick video contest, a response to the contest hiatus forced by COVID-19. Judged on single tricks from 10 of the world’s best street skaters, Huston performed a Caballerial Backside Nose Club to Fakie on the daunting Clipper Ledge in San Francisco, California. His addition to the U.S. skateboarding team in the Tokyo Olympics was another impressive achievement.

18. Cara-Beth Burnside

Born: July 23, 1971

Decade she helped define: 1980s-2000s

Notable achievements: Skateboarding Hall of Fame (2015), Summer X Games Vertical: Gold (2003),1998 Winter Olympics – 4th in Halfpipe, Winter X Games: Gold (1998), 1995 World Cup Snowboarding – 2nd overall, 1996 World Cup Snowboarding – 1st overall

Key videos: Getting Nowhere Faster, Cara-Beth Burnside Vans Triple Crown 2004, Villa Villa Cola Bonus, Cara-Beth Burnside | 2015 | Skateboarding Hall of Fame

Find on Instagram: @carabethburnside

Bottom Line: Cara-Beth Burnside

An X Games gold medalist in skateboarding and snowboarding. A Winter Olympian. Founder and first president of the Action Sports Alliance (a non-profit association of professional female skateboarders). Co-founder of Hoopla skateboards. The first woman to have a signature skate shoe. One of the first to appear on the cover of Thrasher magazine (August 1989). Sponsorship from a non-skateboard company (Swatch).

If there’s something she can’t do — Frontside 50-50? Check. Arching Handplant? Check. Air-to-Fakie? Check — we’ve yet to identify it. Her first skateboarding influence was Duane Peters, the “master of disaster,” which no doubt helped channel a level of fearlessness that’s so linked to her professional identity. She was a pioneer when there were few, if any, professional female skaters. “I was the only one for a long time,” Burnside said. “People would stare.”

She organized a boycott for equal pay that forced ESPN to change its award money. She’s endured multiple concussions, yet she continues to seek new heights. No one has done more to pave the way for the women skateboarders of today.

17. Ray Barbee

Born: Oct. 5, 1971

Decade he helped define: 1990s-2010s

Notable achievements: Honored at California African American Museum – “How We Roll” (2010)

Key videos: Public Doman, Ban This, Propaganda, Propeller, Powell-Peralta Eight, La Buena Vida, 1st & Hope

Find on Instagram: @r.barbee

Bottom Line: Ray Barbee

The second generation of the Bones Brigade did not disappoint, and Barbee was a central figure in upholding — and extending — the sport’s equivalent of the New York Yankees. His fluid style and new approach to street skating established him as a flat-ground innovator, but his background was rooted in ramp and vertical skating. He also led the way in bringing diversity into what had largely been a sport pursued by white surfers. “He set the table for city kids of all stripes and colors to make skateboarding theirs,” said skateboarding great Tony Hawk.

Barbee started skating in 1983 at the age of 12, borrowing a 1970s Sims solid-plank board from a friend. Six years later, he turned pro. His family moved from San Jose, California, to Orange County, California, midway through high school, and his skating rapidly reached new heights. He’s largely credited with transforming the category of tricks known as “No-Complys.”

In an era of pastel-colored clothing and “Flock of Seagulls” hair, Barbee opted for jeans, flannel and a trucker cap. To identify him as the “Happiest Man in Skateboarding” would not be an understatement. He counts Mark Gonzalez, Natas Kaupas and Tommy Guerrero as primary influences. Barbee continues to skate to this day, extending a three-decade career when he’s not playing music or working as a professional photographer.

16. Bob Burnquist

Born: Oct. 10, 1976

Decade he helped define: 1990s-2020s

Notable achievements: Skateboarder of the Year Thrasher magazine (1997), Summer X Games: Gold (2000-01, 2003, 2005, 2007, 2008, 2010-13, 2015), Triple Crown vert champion (1997), one of Rolling Stone magazine’s Athletes of the Year (1999)

Key videos: Bob Burnquist: Being | X Games Minneapolis 2018, Dreamland, Bob Burnquist | The Nine Club with Chris Roberts, Extremely Sorry (featuring his Grand Canyon skateboard base jump)

Find on Instagram: @bobburnquist

Bottom Line: Bob Burnquist

Burnquist’s arrival on the international skateboard scene began a meteoric career that’s yet to reach its arc. After learning ramp-skating in Sao Paulo, Brazil, he showed up at the 1995 Slam City Jam in Vancouver, Canada, and took first place as a 19-year-old, displaying his technicality and switch-stance fluidity that’s become his trademark.

His signature move is the “Fakie 900” (a 900-degree-reverse-natural rotation). In 2010, he became the first skater to land the trick and only the fifth to complete any type of 900 maneuver. “Bob Burnquist is one of the most influential transition skaters, ever,” said Tony Hawk.

Watching him skate comes with a certain amount of holding your breath, and his slams when failing to land are part of the sport’s lore. So too is his classic duel with Bucky Lasek at the 2001 X Games, cited by many as the single-greatest vert contest run in history. As the last skater to perform, he needed a score of 95.5 to win. He scored a 98. Since then he’s moved onto the Mt. Everest of skating — mega ramps. He took them to a new level — clearing 70-foot gaps with stunning ease and flair. He’s widely recognized as the Father of Brazilian skateboarding.

15. Tommy Guerrero

Born: Sept. 9, 1966

Decade he helped define: 1980s-1990s

Notable achievements: Legend Award from Transworld Skateboarding (2013), won first street-style skateboarding contest (1983)

Key videos: Future Primitive, The Search for Animal Chin, Public Domain, Ban This, Amigos

Find on Instagram: @tommyguerrero

Bottom Line: Tommy Guerrero

A founding member of Powell-Peralta’s Bones Brigade team, Guerrero was a multi-discipline skater who could handle himself on vert, but his specialty was the street. He was the first official “street pro.” Starting at age 9, Guerrero rode the steep inclines of San Francisco, California, for blocks, zipping back and forth between the sidewalk and the pavement, improvising with every obstacle in his path.

That never-before-seen “streetstyle” prompted a migration of skaters to San Francisco. That group turned downtown’s Justin Herman Plaza and the city’s famed hills into a global skating hub. Guerrero was also a formidable competitor in the age of the jump ramp, which skaters used to launch abruptly skyward, perform a trick in an eye-blink, then stick the landing.

While he still skates, much of his energy is directed at a successful career as a musician. From 1998 to 2018 he composed, produced and released 10 albums over a variety of genres.

14. Jeff Grosso

Born: April 28, 1968

Died: March 31, 2020

Decade he helped define: 1980s-2000s

Notable achievements: X-Games Skateboard Park Legends (4th / 2010), Transworld Skateboarding cover (October 1994)

Key videos: Anti Hero –Destination Unknown, Anti Hero: The Body Corporate, Future Primitive, Streets on Fire, Love Letters to Skateboarding

Find on Instagram:@grossosucks (primarily content featuring his son)

Bottom Line: Jeff Grosso

Many skaters only know Grosso as the entertaining host of the YouTube show titled, “Love Letters to Skateboarding.” Given its popularity, and the roster of stars that have appeared as guests, it could be said this was his greatest influence on skating. That would greatly diminish his own career, though, which was as high-profile as they come.

His name appears on the Vans shoes website under the “Legends” banner, along with luminaries Tony Alva, Steve Caballero, Christian Hosoi and Cara-Beth Burnside. Grosso was primarily a vert skater, and his handplants on the edge of a ramp or pool were mesmerizing and gasp-worthy, a mix of strength, balance and guts. He’s the inventor of the Roastbeef, a complex midflight grab of the skate deck.

His path from 1980s superstar to beloved historian was a jagged one, derailed by drug addiction (he spoke of overdosing on heroin three times) and other personal issues. Tragically, the autopsy revealed that fentanyl played a role in his 2020 death.

13. Lizzie Armanto

Born: Jan. 26, 1993

Decade she helped define: 2010s-2020s

Notable achievements: World Cup of Skateboarding champion (2010-12), first woman to appear on the cover of Transworld Skateboarding (November 2016)

Key videos: Fire, Saturdays,Lizzie Armanto: BEING, Monster Mentality – Lizzie Armanto,Lizzie Armanto’s 360 loop grabs legend Tony Hawk

Find on Instagram: @lizziearmanto

Bottom Line: Lizzie Armanto

Her soft-spoken nature belies her approach to vertical skating. In a pool or on a ramp, she’s the center of attention. Armanto struck gold in her X Games debut in Barcelona 2013. She followed with a victory in the star-studded Van Doren Invitational in Huntington Beach, California, a year later. Suddenly, the dominoes she’d lined up with years of practice at The Cove Skatepark run by Santa Monica Community Rec began to tumble in rapid succession.

She appeared on the cover of Thrasher magazine (the first woman in 24 years to do so) and became the first woman ever to appear on the cover of Transworld Skateboarding. Tony Hawk signed her to his company, Birdhouse Skateboards, and developed a model in her name. Powell-Peralta issued a signature Bones wheel for her, and Van’s released a shoe for her, the Sk8-Hi Pro.

Her blend of grace, style and aggression is unique. So too is her appetite for challenge. Only a handful of skaters have completed a 360-degree loop. Armanto is the only woman to complete the harrowing, gravity-defying maneuver. She will skate for Finland in the Summer Olympics.

12. Steve Alba

Born: Feb. 6, 1963

Decade he helped define: 1970s-1980s

Notable achievements: 1978 Hester Series at Spring Valley Skatepark – 1st in pool (the first-ever pool-riding contest), 1st in pool doubles, 1978 Hester Series at Newark Skatepark – 2nd in carving, 1978 Hester Series at Big O Skatepark – 1st in pool, 1978 Hester Series at Big O Skatepark – 2nd in pool doubles, 1978 Hester Series – 2nd overall, 1979 NorCal Bowl Riding Series at Milpitas – 3rd , 1979 Lakewood Pro Am Halfpipe Contest – 1st, Skateboarding Hall of Fame (2016)

Key videos: Fruit of the Vine,Right to Exist, Badlands pool skating with Steve Alba, Steve Alba | Vans Pool Party (2011 Pro-tec Pool Party Masters Finals), Santa Cruz Screaming Vlog #8

Find on Instagram: @salba69

Bottom Line: Steve Alba

The man of many monikers (“Lord Salba” and “Le Machine” among them), could simply answer to the title of “King of All Pool Skaters.” No one had ridden more pools, drained and dredged more pools, climbed more backyard fences or upheld the tradition of “barging” than the man who put “the Badlands” on the global skating map.

He won the first official pool skateboarding competition, the opening event of the 1978 Hester-ISA Pro Bowl Series. He dominated a field of established pros, defeating second-place Mike Weed and third-place Steve Olson. Alba was one of the first to master the famed Mt. Baldy Pipeline water tunnel, before dominating the famed Upland Skatepark. Salba was the first to do the Lein Tailslide, the Disco-Rock-and-Roll and Rock-and-Roll shuffles.

He competed well into his 40s, finishing fifth at the high-profile Pro-Tec Pool Party in 2009 against a field half his age. Along with Duane Peters and Steve Olson, he’s credited with ushering punk rock into the skateboard world, a relationship between two temples of youthful aggression that continues to this day.

11. Natas Kaupas

Born: March 23, 1969

Decade he helped define: 1980s

Notable achievements: Inventor of the Nautas Spin, first skater to release a pro-model shoe, Legend Award from Transworld Skateboarding (2005)

Key videos: On the Prowl,Wheels of Fire,Streets of Fire, Speed Freaks, Goin’ Off, A Reason for Living

Find on Instagram: @oscarputdowntheknife

Bottom Line: Natas Kaupas

His legendary career happened almost by accident, a moment at the intersection of genius and chance. The son of Lithuanian immigrants won a local surfing contest, and the prize was a skateboard from a manufacturer known as Santa Monica Airlines — owned by Skip Engblom, co-founder of the legendary 1970s Zephyr team. One year later, the freakishly talented Kaupas was on the cover of Thrasher magazine’s September 1984 edition.

He focused nearly all his energy on street skating at a time when ramps were the rage. The only vertical he pursued was the act of mounting a wall from a flat surface, launching himself and the board without the aid of a transition. The groundbreaking move led to the Thrasher cover shot, blond hair spiked, tanned arms flexed. It’s now recognized as a turning point, not only for his career, but the sport in general.

Kaupas also invented an eye-popping trick that most still can’t duplicate: an ollie onto the top of a fire hydrant, completed by a 720-degree spin and rolling dismount. Dubbed the “Natas Spin,” it crossed disciplines and is now a move pursued by snowboarders.

10. Patti McGee

Born: Aug. 23, 1945

Decade she helped define: 1960s

Notable achievements: Women’s National Skateboard Champion (1964), cover of Life magazine (May 1965), Skateboarding Hall of Fame (2010)

Key videos: Patti McGee 1965 National Skateboard champion TV commercial,Patti McGe Skateboard Champion TV 1965

Find on Instagram: @pattimcgee

Bottom Line: Patti McGee

The graceful Southern Californian was the first female professional skater, drawing sponsorship from the Hobie company to promote their brand nationally during the first craze of the 1960s. At a time when the sport itself was a curiosity, McGee gave it legitimacy, showing that it wasn’t just for “surf bums” or a fad like the hula-hoop or the yo-yo.

She was much more than a pretty face sought by advertising execs of the “Mad Men” era. She set the world record for the fastest girl on a skateboard (47 mph) at the 1964 Dick Clark's World Teen Fair held at the Orange County Fairgrounds. Her photo on the cover of Life showed her performing her signature move — a handstand on a rolling board — leading to an appearance on The Tonight Show with Johnny Carson.

She’s the first woman inducted into the Skateboarding Hall of Fame, entering with a who’s who of the sport — Bruce Logan, Tony Alva, Tony Hawk and Danny Way.

9. Jay Adams

Born: Feb. 3, 1961

Died: Aug. 15, 2014

Decade he helped define: 1970s

Notable achievements: Skateboarding Hall of Fame (2012), 1975 Hang Ten World Pro-Am Skateboard Championships – Junior Men’s Freestyle champion

Key videos: Dogtown and Z-Boys, Jay Adams – the Original Dogtown Boy, Jay Adams Skateboarding – TMZ

Find on Instagram:@jboyadams (maintained by his widow)

Bottom Line: Jay Adams

Fellow Dogtown legend Tony Alva, who knew Adams from childhood, said of Adams, "Some kids are born and raised on graham crackers and milk; he was born and raised on surfing and skateboarding."

Gifted and daring, “Jay Boy” burst onto the scene at the 1975 Bahne-Cadillac Del Mar Nationals, wowing the crowd and confusing the judges, who had no idea how to score his spontaneous routine in the age of four-wheeled choreography. His flowing, surf-influenced style represented a paradigm shift, and his moves helped define the sport’s new frontier. At 15, Adams was featured on the cover of the new Skateboarder magazine (December 1976), bunny-hopping out of a bowl at Carlsbad Skatepark.

As skateboarding boomed in the mid-1970s his skill — and rebel attitude — established him as an icon. That attitude ultimately contributed to his estrangement from the sport as it moved into a corporate, competition-driven era. He was plagued by drug problems in his adult life and served time in prison. Adams regained his sobriety and turned his life around before dying of a heart attack at age 53 on a surfing trip in Mexico.

8. Danny Way

Born: April 5, 1974

Decade he helped define: 1990s-2010s

Notable achievements: Skater of the Year Thrasher magazine (1991, 2004); X-Games Big Air gold medal (2004-06), first to perform the "El Camino" ("Rocket Grab" backflip) on a megaramp, record for "Long Distance Jump" X Games 2004 – 79 feet

Key videos: Waiting for Lightning, Public Domain, Shackle Me Not, Hocus Pocus, Superfuture, Questionable, Danny Way — Great Wall of China jump, Waiting for Lightning (2012 documentary), Danny Way “Thrasher” S.O.T.Y video

Find on Instagram: @dannyway

Bottom Line: Danny Way

It doesn’t get any bigger than rolling down a custom-built megaramp at 50 mph to soar over the Great Wall of China on a skateboard. It doesn’t get any bigger than Danny Way when it comes to four wheels, two trucks and a concave plank of wood. “I’m a little bit of a daredevil,” he admits.

He’s come a long way since winning his first competition at age 11. His resume includes bomb-dropping out of a hovering helicopter onto a mega ramp and bomb-dropping 28 feet from the massive guitar outside the Hard Rock Hotel and Casino in Las Vegas. He also owns the downhill speed record for skating (74.5 mph), set the mark for highest air (25.49 feet) and the longest ramp jump (79 feet) at the 2004 X Games.

But he’s not just a thrill-seeker. Two Skater of the Year awards from Thrasher magazine attest to that. The drive to redefine boundaries has taken its toll. Way reportedly has undergone more than a dozen operations.

7. Daewon Song

Born: Feb. 19, 1975

Decade he helped define: 2000s-2010s

Notable achievements: Skater of the Year Thrasher magazine (2006), Skateboarding Hall of Fame (2017)

Key videos: Love Child, Rodney Mullen vs. Daewon Song, Rodney Mullen vs. Daewon Song Round 2, Cheese and Crackers, 2nd to None

Find on Instagram:@daewon1song

Bottom Line: Daewon Song

The diminutive and dynamic Song was discovered and mentored by the great Rodney Mullen, who observed him riding banks, benches, picnic tables, stairs and, yes, chain-link fences at 135th Street Elementary school in Gardena, California. His technical prowess, creativity and preternatural board control led to major sponsorship, game-changing video segments and accolades from every corner of the skate community.

How popular is he? A promotional video contest, created by one of his sponsors, Adidas Skateboarding (titled “Daewon Did It)” produced close to 2,500 entries by amateurs executing Daewon-inspired maneuvers. The praise is not limited to his fan base. Though quiet, understated, not given to self-promotion, he continues to draw rave reviews from contemporaries. Onetime teammate Daniel Castillo was quoted as saying that “it's too easy for Daewon — he needs something else.”

His enthusiasm and talent can’t be contained. During the COVID-19 lockdown, he released videos of him skating the interior of his home as if it were a concrete playground.

6. Christian Hosoi

Born: Oct. 5, 1967

Decade he helped define: 1980s-2000s

Notable achievements: 1988 Titus World Cup (1988), Ramp Riot Bells Beach Australia (1st / 1988), Japan Slam Jam (1989), X Games Legends champion (2009-10)

Key videos: Rising Son – The Legend of Skateboarder Christian Hosoi, Hardflip, Thrashin’, Radical Moves, Speed Freaks, Wheels of Fire, Rising Son – The Legend of Christian Hosoi

Find on Instagram: @christianhosoi

Bottom Line: Christian Hosoi

Skating’s first true rock star launched his career by going pro at 14 after turning the Marina Del Rey Skatepark (managed by his father) into a personal playground. Riding in the shadow of Dogtown legends and park regulars like Tony Alva, Jay Adams, Shogo Kubo and Stacy Peralta pushed him to break boundaries in search of respect from his much-older peers.

His stunning blend of power and grace and lust for the spotlight vaulted him to the icon status that still defines him. His mid-1980s rivalry with Tony Hawk propelled the sport to new heights. The celebrity came at a cost, however, in the form of drug addiction. Facing an arrest warrant and in hiding, he declined to compete at the first X Games (he won titles in 2009 and ’10).

Later, he served time in prison on trafficking charges after being apprehended trying to transport drugs from Hawaii to California. But the inventor of the Rocket Air and the Christ Air found redemption. Today, he’s an ordained associate pastor as well as a leading spokesman for the sport.

5. Steve Caballero

Born: Nov. 8, 1964

Decade he helped define: 1980s-1990s

Notable achievements: Skater of the Century Thrasher magazine (1999), Skateboarding Hall of Fame (2010), Gold Cup – Upland (1980), Kona/Variflex Summer Nationals Contest: (1981), World Challenge Pro Contest (1982), Summer World Series at Del Mar (1983), NSA Summer Olympic Series (1984), World Champion Street and Vert (1987), Legends Champion – Vans Pool Party (2017)

Key videos: The Search for Animal Chin, Future Primitive, The Bones Brigade Video Show, Bones Brigade: An Autobiography, 1985 Rage in the Badlands part 2 of 5

Find on Instagram: @stevecaballero

Bottom Line: Steve Caballero

In the 1980s, at a time when the skating universe was centered in Southern California, a shy unknown with curvature of the spine arrived as a game-changer from up North. He was quickly recruited at age 14 by Stacy Peralta to join the Powell-Peralta company, an association that continues to this day. It’s no surprise that he counts daredevil Evel Knievel as a childhood hero. Instead of a motorcycle, he rode a skateboard.

Caballero quickly established himself as the skater by which others measure themselves. He invented the game-changing “Caballerial” (a fakie 360 aerial), the Backside Boneless One and the Frontside Boardslide. He won 31 contests over a 20-year span. In 2000, he established the record for the longest board slide, a harrowing descent down on a handrail adjacent to a 44-step staircase. And he also set the record for biggest air; in 1987, he soared 11 feet above a half-pipe, a mark that stood for nearly 10 years.

As a founding member of the Bones Brigade, he traveled the world, establishing himself as an ambassador and friend to all. Additionally, he’s a professional artist and successful musician. Today, the global skate community knows him simply as “Cab.”

4. Mark Gonzales

Born: June 1, 1968

Decade he helped define: 1980s-1990s

Notable achievements: Transworld Skateboarding”Legend Award (2006), Transworld Skateboarding Most Influential Skateboarder of All Time (2011)

Key videos: Psycho Skate, Blind: Video Days, The Truth Hurts, Kicked Out of Everywhere, Streets: San Francisco, Rocket Science, Kronichles, A Five Day Excursion to Paris, Naughty, Diagonal, Cherry, Away Days

Find on Instagram:@krooked (his skateboard company)

Bottom Line: Mark Gonzales

Widely regarded as one of, if not the, most influential skateboarders of all time, “The Gonz” elevated street skating to the modern form we see today — riding handrails, leaping sets of stairs and mounting vertical walls by sheer force.

With a personality as quirky and original as his riding style, Gonzales approached every piece of urban terrain as if it were designed for skating. He didn’t just create new moves, he transformed random pieces of concrete into parts of skating history. Do a search for the “Wallenberg Set” or the “Gonz Gap” and you see why his legacy stands alone.

In addition to his riding, he launched successful skateboard companies and emerged as a sought-after artist. In 2017, his work was featured in an exhibition, titled “Flower Power,” at L.A.’s HVW8 gallery. He’s also featured at the Franklin Parrasch Gallery in New York.

3. Rodney Mullen

Born: Aug. 17, 1966

Decade he helped define: 1980s-1990s

Notable achievements: Transworld Skateboarding Skater of the Year (2002), Skateboarding Hall of Fame (2013)

Key videos: Future Primitive, The Search for Animal Chin, Public Domain, Rubbish Heap, Virtual Reality, Questionable, Rodney Mullen vs. Daewon Song, Rodney Mullen vs. Daewon Song Round 2, Bones Brigade: An Autobiography, Evening Magazine Rodney Mullen 1983

Find on Instagram:@rodneymullen

Bottom Line: Rodney Mullen

As a founding member of the Bones Brigade team, Mullen demonstrated an originality and creativity that remains unmatched. His specialty wasn’t vertical. His moves were not “bionic,” skaters’ parlance for powerful high-flying tricks. Instead, they were what’s known as freestyle — controlled, precise, performed on flat ground and, in his case, virtually impossible to duplicate.

He mastered most of the moves in solitude, living in rural Florida, but he faced stiff opposition from his father. “He thought I'd get hurt and never get good, and the culture was bums, and I'd turn into one,” Mullen said.

He won 34 of the 35 contests he entered as a pro, turning the skateboard into a three-dimensional object by riding every part of it. Appropriately, he’s known as the "Father of Street Skating." In 1981, “Mutt” created a trick known as the Flatground Ollie — the rider slamming the board’s tail onto the concrete to get it to “pop,” with all four wheels leaving the pavement from the impact. Today, it’s the most important element in skating, the first trick that any young skater seeks to master. Additionally, he invented the Kick-Flip, the Heel-Flip, the Impossible (aptly named), the 360-Flip, Ollie Nosebone, Ollie Airwalk, Casper Slide and many, many, many more.

2. Tony Alva

Born: Sept. 2, 1957

Decade he helped define: 1970s-1980s

Notable achievements: USA World Invitational Skateboard Champion (1975), Skateboard of the Year Skateboarder magazine (1976), 1975 Hang Ten World Pro-Am Skateboard championships – barrel jump and pro cross country champ, 1977 California Free Former World Championships – barrel jump champ

Key videos: The Tony Alva Story, Dogtown and Z-Boys, Skateboard Kings, Tony Alva in Tournament Old Skool (ABC Sports video), Tony Alva 31’ pipes (1978), Tony Alva 1981 Skateboarding, New 2019 Tony Alva (4K),

Find on Instagram: @thetonyalva1957

Bottom Line: Tony Alva

The Godfather of vertical skateboarding and his West Los Angeles skating mafia largely pioneered the art of riding empty swimming pools, a by-product of their surf skills and an historic drought that struck California in the mid-1970s. The Z-Boys’ appetite for risk (most of the backyards were off-limits) and athleticism (the terrain was uncharted) transformed the sport from its ground-based, gymnastics-influenced roots into the aerial circus (and commercial juggernaut) we see today.

As skateboarding’s first superstar, Alva did it all — freestyle, slalom, pool-riding, ramps and, yes, barrel-jumping! His skating, and his lifestyle, was a thinly veiled blend of aggression and defiance that became the modern skating ethos. He was credited with performing the first frontside air in a swimming pool. He is the first skater to start his own company (Alva Skates) at age 19, which he runs to this day.

He was the centerpiece of the acclaimed 2001 documentary, “Dogtown and Z-Boys,” which was followed by the feature film “Lords of Dogtown.” He also played the antagonist to a young Josh Brolin in the skateboarding cult classic “Thrashin’” (1986). Alva continues surfing and skating vertical today well into his 60s.

1. Tony Hawk

Born: May 12, 1968

Decade he helped define: 1980s-2010s

Notable achievements: Skateboarding Hall of Fame (2009), Skater of the Year, Thrasher magazine (1990), 12-time Vertical Skating World Champion, X Games Gold (1995, 1997-2003); Silver (2001, 1996); Bronze (2002, 1999, 1998)

Key videos: The Search for Animal Chin, Future Primitive, The Bones Brigade Video Show, Bones Brigade: An Autobiography, 1985 Rage in the Badlands part 2 of 5, Tony Hawk’s first ever 900! Tony Hawk Lands 900 at 48! Tony Hawk’s Loop of Death – Slams, Attempts, Makes, Tony Hawk: 50 Tricks at Age 50

Find on Instagram:@tonyhawk

Bottom Line: Tony Hawk

The world’s most famous skateboarder burst onto the scene in the 1980s as a gangly teen, turning pro at 14 and going on to win more than 80 contests. His encyclopedia of moves (he’s credited with inventing more than 80 tricks) left a lasting mark on the sport. His signature lack of fear left a lasting mark on his smile — early on, he knocked out his front teeth with a slam at the famed Del Mar Skate Ranch.

That willingness to push limits led to the unforgettable 11-attempt, gravity-defying sequence at the 1999 X Games, which climaxed with the first “900” (2.5 rotations above a vertical ramp; Hawk’s personal Holy Grail) in skateboarding history. Shunned in school, where skating was viewed as a pursuit for outcasts, he stayed true to his craft. “When I started skating, it was such a small community. You didn’t aspire to be rich or famous or make a career out of it because that wasn’t something anyone had done yet.”

He retired from competition in 2003. Hawk also oversees his hugely successful video game series, the Tony Hawk Foundation, which has built hundreds of skateparks in disadvantaged communities, and Birdhouse Skateboards. His net worth is well in excess of $100 million.