Skateboarding first started as a counter cultural revolution by surfers searching for thrills when the waves were lacking. But quickly this original band of California-based icons transitioned into the mainstream. Beginning with the legends of Dogtown who went on to found multi-million dollar skateboard empires like Powell-Peralta and G&S, skateboarding has continued to thrive in each subsequent generation. Some professionals have accrued astonishing amounts of wealth through the sport via video games, brand deals, and television shows. Recently, skateboarding has jumped another gap into the mainstream, becoming an official Olympic sport with the USA forming its own competitive team. The team is set to debut at the 2021 Olympic Games in Tokyo, Japan.

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But even though the sport has entered into the mainstream and morphed from a means of artistic expression into a competitive sport, some people have retained the rebellious nature of the art and the integrity of skateboarding altogether. Always finding its way within a niche mix of cultural icons, a few celebrities have carried the torch of the original intent of skateboarding. Here are a list of some surprising celebrities who have advanced the culture and turned it into a profit in the process.

Jonah Hill

Jonah Hill is known for both his iconic comedy roles like Superbad, 21 Jump Street, and Knocked Up, but also for his dynamic performances in dramas like The Wolf of Wall Street, Moneyball, and Django Unchained. Recently, he built upon his acting and experiences with legendary directors to make his own feature film. His directorial debut was the 2018 feature film Mid90s. The film is semi-autobiographical and features the stories of several skateboarders growing up in Los Angeles in the 1990s.

While some press outlets have questioned Hill's involvement in the skateboarding industry, Jenkem Mag, an integral magazine dedicated to skateboardings culture featured an interview and investigation with Hill that included certain pictures and clips from his skateboarding experiences. The film was a success, earning a gross income of around $10 million with a budget of only $1.7 million. Jonah Hill continues to propel the skate culture as well, casting some of the best recent skaters in the film such as Na-kel Smith and Sunny Suljic.

Jason Lee

Known for his portrayal of the titular character in the comedy series My Name is Earl, Jason Lee first started his career as a professional skateboarder. He was originally sponsored by the Blind company and was known for having some of the best tre flips in the sport. He appeared in the legendary video Video Days. After turning professional, went on to form his own skate company Stereo Sound Agency with legendary skateboarder Chris Pastras.

One of his skateboards from his 1991 time on the Blind team is one of the most valuable collectibles in skate culture, estimated at around $6,000.

Spike Jonze

Spike Jonze is a legendary director who is known for his Academy Award-winning feature films like Adaptation, Her, and Where the Wild Things Are. He is also known for having made some of the most viewed and culturally relevant music videos including the Kanye West and Paul McCartney video for "Only One" and the Arcade Fire video for "The Suburbs". But prior to his career as a director, he was both a skateboarder and a documentarian of its culture. He shot the first cover for the legendary skateboarding magazine Big Brother and also produced and directed some of the most important skateboarding films of the culture including Mouse, Fully Flared, and the Yeah Right!. Spike Jonze was also the co-founder of the one of the most popular skate brands of all time Girl Skateboards. During the release of his film Where the Wild Things Are, he also released a series of skateboards featuring screen shots of characters from the film which now sell for over $300 a board. He has also appeared on the skateboarding podcast The Nine Club where he discussed his involvement innovations in the sport.

Shia LaBeouf

Known for his trend setting fashion styles that have spawned their own Instagram accounts, Shia can be seen on several occasions wearing the iconic skateboarding magazine Thrasher T-Shirt. The shirt has also been worn by other mainstream celebrities including Ryan Reynolds and Rhianna. He can also be seen rolling around on a board as well. He often rides some of the most expensive longboards including the Jucker Hawaii valued at over $200.

Lil Wayne

Lil Wayne is known for his popular rap albums that have shaped the culture and ushered in a whole new genre within the music category like The Carter III. Recently, he chose to explore the world of skateboarding as well, helping expand his image. He is often seen on Instagram at the iconic Berrics skate facility located in Los Angeles. He even built his own mini ramp featured in his music video for his track "Loyalty".

Jack Black

Jack Black has often been the purveyor of counter-cultural revolutions. From the Richard Linklater film School of Rock to forming his own rock band Tenacious D, Black has continued to participate in the music scene as a breath of fresh air when it comes to keeping the spirit of the genre alive. Recently, in between shooting some of the most iconic films of the decade, he has been releasing a series of self-produced sketches through his Instagram that have featured clips of him skating on the mini ramp he built in his own backyard.

He also recently shared some clips of him skating at the legendary Berrics skate facility, participating in the now iconic "Do a Kickflip" challenge.

Heath Ledger

Heath Ledger was known for portraying some of the most iconic characters in film from the Batman villain The Joker to Skip Engblom, the original pioneer of skateboarding himself. But prior to his career as an actor, Ledger was a skateboarder. He often cited the Lords of Dogtown as a huge influence as a child. But the passion for skateboarding didn't stop in his childhood either. A possibly doctored photo of him on set of the film The Dark Knight shows him in character kickflipping over Batman during one of the films street scenes. Regardless of the truth of the picture, Ledger's passion and contribution to the culture is very much authentic, including this clip from him skateboarding on set.

Miley Cyrus

Miley Cyrus is also known for upholding cultural traditions through both skateboarding and her music. Beyond teaming up with the legendary alternative group The Flaming Lips, she is also known for having been spotted skating through her Beverly Hills neighborhood alongside her then-partner Liam Hemsworth.

Justin Bieber

Pop sensation and arguably the most popular celebrity on this list according to his Instagram following, Justin Bieber is also known for his passion for skateboarding. Beyond releasing several photos of him shredding, Bieber took the art to the next level, releasing his own skateboard to celebrate his tour Believe. He is also known for having skated on stage during some of his performances as well. YouTube released a video featuring some of his best (and worst) stunts that he's performed on stage.

Skateboarding has been an iconic art since its first inception in the 1950s. And even though the sport has made some recent leaps into the mainstream through the olympics, video games, and through the sport who has produced its own set of stars like Rob Dyrdek and Nyjah Huston, the art and its counter cultural roots are still being carried on by the most unlikely of figures, celebrities.

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Sources: GoSkate, Mpora, Pintrest, LiveAbout, EZine, Inc, StyleCreations, MasterClass, TVGuide, GQ, DailyMail, TheNumbers, HypeBeast, TheBoardr, MSN, Transworld, Racked, PopSugar, NoirnNola, Grammy, NYPost, Skatesphere