Everyone likes to shred. From kids to adults and from your average Joe to A-list celebrities. It’s very cool to see people with so much money and social clout choose to skateboard. They could literally do anything with their free time and they chose skateboarding! That’s cool.
I love to see enthusiasm for the sport and it’s always interesting to me to see a celebrity who I wouldn’t imagine to skate actually skateboarding.
This list isn’t completely exhaustive and I won’t include lesser-known celebrities or else this article would never end.
Anyway, let’s dive into it.
Lil Wayne
Lil Wayne is probably the most enthusiastic skater on this list and also is one of the best. He regularly gets out to skate and you can find videos of him doing lip tricks and doing pop-shuvits off of kickers. He also has his own private skatepark. He’s a cool person and is pretty outspoken about how much he likes skateboarding.
His interest in skating has lead him to release his own skateboarding clothing line called Trukfit. The designs are a mix of street-style Lil Wayne designs. I think the shirts and hoodies are pretty standard, but he has some pretty cool cargo pants designs.
I think musicians are drawn to skateboarding much more than actors or other artists are, but I may just have a skewed point of view. Lil Wayne back in the late 2000s was great. The “A Milli” and “Lollipop” era were peak Lil Wayne years for me although I know he has a large cult following from his insane number of mixtapes that he put out.
Still cool a musician who is also passionate about skating out there.
Tyler the Creator
Tyler the Creator is a hyper-prolific beast with many talents. Is skateboarding one of those talents? Maybe it wasn’t developed like his musical ability, but he definitely enjoys skating and was pretty capable of hit handrails and more.
Tyler has been skating since he was 11 and does have a good bit of control on his board. He got a clip in Supreme’s first skate video “Cherry” and he used to spend time with the Illegal Civ crew in the early 2010s. He has talent.
He recently dropped Call Me If You’re Lost as I write this and the album is a banger. Massa is probably the best song on the album. Check out his clothing brand Golf Wang. It’s a cool mix of street style and classic dress clothing. There is little street style inspiration in your average polo, but Golf Wang changes that a bit.
Jason Mamao
There is a pretty sick video of Jason Mamoa skating a mini half-pipe. This is not typical celebrity behavior.
Jason is the star of movies like Aquaman and played an iconic role in Game of Thrones. He is pretty outspoken about his interest in extreme sports from surfing and rock climbing to skateboarding. Otherwise, he is a native Pacific Islander who is an outspoken proponent of his culture and even performed a Haka, a traditional Maori culture dance, at the Aquaman premiere.
He’s a cool guy and doesn’t skateboard very regularly, but he’s clearly put in some time on the board.
Jonah Hill
Jonah Hill is an actor first and foremost with an impressive catalog of movies behind him. He is open about trying new things to improve himself and has a famous tweet about him facing his fears and trying Judo for the first time. He is a cool and down-to-earth person. He also directed a raw and honest skating film titled Mid90s.
He skated as a kid in California in the mid-90s and this became the inspiration for his directing debut. He openly talks about how he was a terrible skateboarder, but it came into his life at the right time to give him an outlet for his frustration with growing up.
There really isn’t much video or pictures to find of Jonah skating, but he talks about it pretty openly in interviews like one he does here.
Owen Wilson
Wow.
There is a funny video clip in Yeah Right where Owen Wilson talks smack about all the other skaters trying to film parts and then lands blunt slides on a handrail on the first try. Obviously, it’s fake and the person blunt slides the rail is Eric Koston, but the video is hilarious so I wanted to include this in the list.
So yea, Owen Wilson can’t actually skate, but he is funny and I love him in Zoolander. So wow. Watch the staged skateboarding clip that made people think he actually skates below.
Beto O’Rourke
Beto O’Rourke rose to national fame while running for Senate against Ted Cruz in 2018. The politician is surprisingly progressive for coming out of Texas, good-looking, and charming. He kind of reminds me of an Obama-style politician.
During his campaigning, he did quite a few things to attract voters and in particular younger voters on who he was relying on. One of these things was skateboard across the Corpus Christi stage at Del Mar College. No, he does not actively skateboard and yes, this was really just a campaigning trick.
But, he still did step on and push off on a skateboard in dress clothes and that has to count for something! Check out the short clip below if you’re interested.
If you want to see videos of cute dogs skateboarding and maybe train your own dog to skate, then check out our curated list here.
Rich the Kid
Rich the Kid is a rapper and he skates. He is actually pretty good at it too. You can definitely find videos of him doing heelflips off of ledges and flat ground varial tricks.
He was raised in Georgia and New York to Haitian parents and has multiple platinum songs with superstar artists such as Kendrick Lamar and Chris Brown.
It always makes me happy to see these celebrities who are so well connected and rich that still choose to skate. They could do anything else, but they work on kickflips with their friends. This is awesome. Rich the Kid is awesome. Check his videos out and of course, stream some of his music.
Justin Beiber
Justin Beiber evokes mixed feelings from most people. He went from a child and teen celebrity sold as a boy crush for preteen girls to a worldwide pop artist that collabs with DJ Khalid, Drake, and plenty of others. He lost his cute boy next door image and got covered in tattoos and become an international pop star.
He also has tried skateboarding quite a few times even bringing a skateboard on stage while performing once to try a few tricks. He really isn’t bad and can land some varial tricks on flat ground at least.
He gets a lot of unnecessary hate as an artist and as a skater because he has a reputation for being flashy, but at least he’s out here trying to do tricks and consistently skates. There are tons of “skate fail” videos of him that get views because people love to hate on him, but he is never actually bad in the videos.
So yea, give Justin some love. Below is a good skateboarding video of him with Nyjah Hudson. Skip forward a bit to see Justin.
Heath Ledger
Heath Ledger had been surfing and skating since he was just a kid growing up in Australia. The actor who was most famous for his role as the Joker in The Dark Knight and has a very impressive catalog of films otherwise was also a pretty talented skateboarder.
This made him perfect to star in Lords of Dogtown which was a movie about the influential Southern California skateboarding crew.
The real controversy about Heath Ledger was the digitally altered image of Joker doing a kickflip of a prone Christian Bale as Batman on the set of The Dark Knight. This image blew up the internet and still fools people into thinking that it’s real. It is not. Heath Ledger left his skateboarding days behind in Australia for the most part and the image was examined and proven to be digitally altered.
The late actor did have a skateboarding history though.
Pharrell
Pharell is most famous for being the lead vocalist for NERD and the soundtracks for Despicable Me and Despicable Me 2. He is a talented and recognizable musician who expanded his musical catalog well beyond a conventional hip-hop artist. He is also an entrepreneur who has his own fragrance collaboration among other projects.
He is a friend of Tyler the Creator so maybe it isn’t too surprising that he also skates a bit. There isn’t much evidence around of him riding on a board and the videos that exist show that he is definitely a beginner skater, but still, it’s always cool to see a celebrity known for something completely else give skateboarding a try.
Kanye West
Kanye West is someone who is a bit controversial. He is incredibly influential as an artist with many top albums that some argue changed hip-hop in the 2000s. However, his ego and mental health issues have gotten him into trouble. As of writing this, he is staying with his team in the Mercedes Benz stadium while finishing the DONDA album named for his late mother. He keeps pushing back the release date while hosting many listening parties and no one knows what to expect.
Anyway, other than his music and clothing lines, he has dabbled with skateboarding. When I say dabble, I mean he has stepped onto a skateboard before. There is footage of him learning to ollie in 2018 and obviously not getting it.
Still, it’s cool to see a superstar like Kanye hanging out at a skatepark.
Miley Cryus
Miley Cyrus is a bit like Justin Beiber. She grew up as a Disney star and was a clean image musician for Disney until she turned eighteen and then went rogue. She got tattoos, wrote sexually explicit content, and completely changed her image.
It was her Wrecking Ball video where she is simply naked while riding a wrecking ball that I realized that she was deliberately and effectively eviscerating her previous image as a teen pop star.
She also had a brief stint with skateboarding where she should even post on Instagram about wanting to go skate. She is definitely a beginner and seems mostly to have cruised around at this time.
There is also a famous video of “Miley Cyrus” skating at a skatepark. It is a man dressed in a Miley Cryus costume and he crushes it. It is not dear old Miley herself.
Steve-O and Weeman
I’m including Steve-O and Weeman together here only because they originally got famous together through working with the Jackass series. Since then they have gone their separate ways. Weeman is skating a lot and has his own line of skateboard decks. Steve-O battled addiction for years and now helps others overcome their addiction and he speaks out against drugs pretty actively.
There are tons of sources and videos of Weeman skating and he’s good at it. He currently rides with the Nullity skate team.
Steve-O actually sells his own skateboard decks as well from a website that has a bunch of gear that features his face on it.
Kyrie Irving
Kyrie Irving really has no business skateboarding. He is a professional basketball player and a very successful one at that. His managers would probably be mad if they thought he was risking injuring himself to skateboard. But he has done just that.
You can tell that he doesn’t spend too much time on a skateboard, but looks surprisingly comfortable. We know his career requires he train exclusively for basketball so it’s cool that he even tried to skateboard. Again he has no reason to do so other than a genuine interest.
There is really one famous video of him skating and he is clearly having alot of fun. It’s well shot so give a watch.
Matthew McConaughey
Matthew McConaughey is handsome and is a well-recognized actor. He surfs as is expected of someone who looks as blonde-haired and seemingly naturally has a beach bod. You may not agree that he is a great actor and you might be right. He is mot famous for supporting roles rather than leading roles. But he is a talented supporting actor and he is naturally athletically inclined.
There are photos aplenty of Matthew skating around Los Angeles in his forties. It is fun to see someone using skating to relax. He doesn’t seem to have any interest in doing tricks, but just cruises. That’s ok too. Cruising is awesome too.
Jaoquin Phoenix
Is there a requirement that to play the Joker you must have skateboarding experience?
Probably not, but it is an interesting coincidence. Jaoquin Phoenix is an American actor and producer. He has also directed music videos and is active in the animal rights movement. He’s just an all around cool dude.
Jaoquin grew up skateboarding and there is an anecdote that he gave burritos to and skated with some of the crew who were filming the movie Her. (source)
There isn’t much skateboarding media showing Jaoquin except for some photos he took with the New York Times for an articles. I didn’t include them here because I don’t have permission to use those photos. You can find that article here though. It’s behind a paywall.
Dave Chapelle
Dave Chapelle is a funny man who grew to comedic superstardom with his iconic bits about race. He had a wildly successful show called The Chapelle Show, but then suddenly gave it all up. He didn’t want to sell his soul and his comedic integrity for a paycheck.
He gave back a few years ago, now in his forties, and has released a couple of specials that are notedly different from his original comedic style.
He also has been seen around with a skateboard and he openly mentions loving skating as a hobby. He is known to visit different skateparks and has rented out SPoT in Tampa allegedly.
Despite there being many videos of him being open about skating, there are very few if any good clear videos of him skating. If you find one reach out to me.
Jaden Smith
Jaden Smith is the most famous of Will Smith’s sons. He is a musician and actor that has somewhat followed in the footsteps of his dad. Whether you think he is actually talented or not is up to you. There are plenty of tweets and posts of his from when he went through a very public coming of age that are kind of weird to read. But then again we all said some silly things when we were young.
Anyway, Jaden also skates. he clearly has spent some time learning to skate and you can find lots of videos of him doing flat ground tricks and even doing an ollie off of some stairs. He isn’t the best skater, but it’s cool to see him take an interest in skating.
Also, his dad is an amazingly positive and humble guy for being so famous.
Jack Black
Jack Black is a very energetic actor, comedian, and musician. His biggest flims might be School of Rock and Kung Fu Panda and the man is clearly living out his dreams. Who doesn’t want to skate, play music, and act in movies?
His is very active on social media with mostly comedic skits that have zanny over-the-top energy, but he is clearly a relaxed and down-to-earth guy. There are tons and tons on videos and images of him skateboarding. This is not a secret.
He clearly has spent some time on a board and has a mini in his backyard to practice on, but he is by no means extremely talented. You can tell that he skates for the fun of it. Follow his YouTube because he is a funny man.
Nyjah Hudson
This one is funny to me. Nyjah Hudson is most famous for his notoriously difficult-to-spell name (Nigel Houston?), but he also actually skateboards! Whoa.
You can see from his Instagram that he picked up skateboarding sometime this year as he has posted a few videos. He’s actually pretty good for little he’s been skating. Maybe if he keeps at it he could get a sponsor or some recognition. Who knows if that’ll ever happen though. It’s 2021 and he’s already in his late twenties.
If you’re curious about where you can skate locally and how to find a good skate spot, check out our where to skate guide here.
Conclusion
In conclusion, there are some great celebrities who shred out there. I focused on big-name celebrities and artists that I personally like, but there is so much more out there as well.
There are some celebrities who simply stepped on a skateboard once that I didn’t include (with exception of Beto and Kanye). This include Obama and some others.
Does your favorite celebrity skate? I just realized that maybe that’s a silly question as I don’t really have a favorite celebrity myself. Favorite musician, sure, but not a favorite celebrity.
Anyway, thanks for reading, and look out for more articles from Board and Wheels.
