Tom Penny: The Mystery of The World's Greatest Street Skater

Tom Penny is known by most skateboarders to be the greatest street skater on earth. However, his hermit lifestyle and the secret mythos that surrounds him has given him a living legend status...
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Tom Penny is known by most skateboarders to be the greatest street skater on earth. However, his hermit lifestyle and the secret mythos that surrounds him has given him a living legend status...


Normally when you’re doing any sort of research on a successful sporting hero via the internet, Google does all it can to throw as much information, relevant or not, down your throat. In the case of Tom Penny, British skateboarding legend, quite the opposite is true. Apart from the numerous videos of him skating, the internet shies away from showing any grounded information on his actual life and instead tries to make you question whether there really is all that much of a story behind this highly acclaimed, Dorset-born skater.

Penny started skating in Oxford at a young age with no external skating influences other than the friends he skated with. Skating itself had not yet become what it is today, there simply weren’t that many skaters around him and so the culture was of an esoteric nature, especially in Oxford. It wasn’t until he gained the sponsorship from ex-pro Sean Goff and moved to the US that he started to gain real coverage from UK skate magazines such as Skate and Rad. He was added to the Deathbox skateboards team (now rebranded Flip) and at the age of just 15, featured in Flip’s opening Video ‘The Long Overdue.’ By 1996, Penny had placed both 3rd and 1st in the UK Championships at Radlands, received acclaim from the likes of Tony Hawk and been on the front cover of Transworld. He was just 19 years old.

So surely after the magnitude of events that seemed to surround Penny’s life from such a startling early age, there must be a library full of information surrounding him? If that time was anything like today, where we see young sportspeople thrust into the limelight, given million pound endorsements then there most definitely would have been. But Penny is from an era where not only celebrity status was itself a far lesser burden to carry, but skateboarding simply didn’t have it.


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The first ever skateboarding game was made in 1987, some 30 years after the very first sports game. It wasn’t until the popular Tony Hawk’s Pro Skater series arrived in 1999 that skateboarding officially had a place in the sports-game market. When you consider almost all other sports had had a mention in the gaming world by this time, it’s not difficult to see just why someone like Penny went almost unnoticed outside of the skating world.

Coupled with skating’s already introverted social scene, Penny has always been a very humble, modest man. In an interview in 2012 he was asked what influence he thinks he’s had on skateboarding. He simply replied ‘I’m not too much of a showy offy’’ person…’

There’s false modesty that comes with someone desperate to be seen as a role model to younger generations, then there’s Tom Penny, who is simply happy not to be seen. His clothing style has remained the same as it was when he was in his late teens, as does his long hair. Most importantly of all though, the style in which he skates has not changed since he was 13 years old.

It’s said that he has a habit of jumping down flights of stairs without looking how far down they go and his board always just seemed to be an extension of himself because of how fluidly he can skate. Skin Phillips, Transworld’s editor in chief said, ‘He (Penny) sort of didn’t realize—I don’t think he’s ever realized the impact he’s had on skateboarding.’

In all investigative research, there comes a point where you expect demons of someone’s past or present to start emerging, and in Penny’s case, it would seem that drugs are was one of his. Stories told about how he had to run away from a competition once a bag of marijuana had fallen from his sock appear on the internet after a little bit of digging. These are followed by people posting YouTube clips depicting scenes where he’s skating almost unconsciously and appears lost in his own world. Chad Muska, when talking about Penny’s style of skating, says ‘None of it was conscious. Nothing he’s done has been conscious.’ Though this comment was obviously said tongue in cheek, there’s an awareness that Penny’s hobbies extend further than simply skating.


Arnold Schwarzenegger has often been questioned about his use of steroids in becoming a bodybuilder. He has never denied it. In fact, he says that at the time steroids were as much a part of bodybuilding as training and diet. Everyone was doing it, everyone knew they were doing it and it wasn’t an issue. Only now when research has proven the negatives of using them is it so severely frowned upon. I suppose the word here is synonymy. Relaxing and escaping drugs such as marijuana and magic mushrooms were as synonymous with such sports as skateboarding, surfing and other similar individualist hobbies back in the 90’s as steroids were with bodybuilding. They culturally and physically go hand in hand. Penny has described skating as ‘mind melting’ on numerous occasions. It is a prerogative to make your favourite sport as relaxed and fun an experience as possible and if there are stimuli in the world that maximise this, then who’s anyone to say not to do it.

People nowadays compare the current sporting heroes to those of the olden days. In doing so, people become naturally ethnocentric and their arguments ultimately reach no conclusion. Penny is incomparable to the skaters within this era because skating has changed immeasurably. He embodies a culture, both in his clothing and spiritually, that was very much of the 1990’s era, an era now dead. In any case, at that time all evidence points to him being a separate entity anyway. He was and remains a hedonist, just doing what he loves, rather than someone who obsesses over rankings and glory. He has already been classified as one of the most influential skateboarders of all time. His indifference to this high praise is what makes him so great and typifies why he is a role model.

If you liked this article and are after more British skateboarding info, check out RANDOM, an extreme sports blog focused on the UK scene.

This article has been written by Jack Gordon Hughes. You can reach him via Twitter @jackgordonhuge for more info.