21st Most Influential Skater Ever, Tom Penny Spends His Life Vanishing: Why?

December 2011. Transworld dropped their all-time most influential skaters list. Tom Penny landed at 21st. A dude from Oxford, England, ahead of dozens of US pros who’ve bagged more, filmed more, sold more.

The thing is, this dude spends a good chunk of his career bouncing in and out. He steps away, comes back, dips out again. And every time he resurfaces, everyone hits rewind.

How do you become an absolute legend while being so off the map? The answer’s in one sentence, and it ain’t where you’d expect.

Oxford, Before Everyone Else

First off, let’s get the facts straight. Tom Penny was born April 13, 1977, in Dorset according to 411 Video Magazine. He grew up in Abingdon, a town in Oxfordshire, and started skating in Oxford. Not Bristol, despite what you might’ve read here before this correction.

Back then, as he tells it: no magazines, no shops. Sean Goff from SS20 hooked him up, then Jeremy Fox brought him into Deathbox, the UK brand that’d become Flip. In 1993, at sixteen, he was in *The Long Overdue*, Flip’s first video, and in issue #2 of 411. That same year, he took third at the UK Championships in Radlands, Northampton.

Two years later, in 1995, he snagged 'em. Wikipedia lays out the scene: over a hundred competitors, with more than 75 of 'em being American pros.

Read too : 1993, a VHS, a 16-year-old Brit: how did Tom Penny make all the American pros switch up their style?

The Style Nobody Can Explain

In 1994, Flip relocated to Huntington Beach, California. Penny was seventeen. And that's when the pros encountered something they'd never witnessed.

The same year, Hi-5, Etnies' video, dropped, featuring his part. Andrew Reynolds summed up his skating in two words: "It's unexplainable." Paul Rodriguez, in 2013: "For me, his style was my favorite."

What they're describing is a way of moving. Tricks landed with seemingly zero effort, the upper body staying chill while the board did the heavy lifting. You can copy a trick in an afternoon. A vibe, never.

2000, 2002, 2003: The Tapes We Wore Out

If you were fifteen at the start of the 2000s, you know the sequence by heart. Menikmati, the éS video, in 2000. Then Sorry from Flip in 2002, and Really Sorry in 2003. The Hall of Fame states it plainly: his parts for éS and Flip set new style standards.

The detail that mattered is his name was on the boards too. According to Wikipedia, his Flip pro model in Cheech & Chong colors was one of the brand's best-selling decks.

And then, between the parts, there were the gaps. Periods where Penny was nowhere to be found. No tours, no videos, no news. The UK mag Sidewalk listed the places he lived in recent years: Argentina, Barcelona, Christiania in Copenhagen, England, the USA.

Why He Disappeared, And Why It Didn't Cost Him a Thing

So, that answer. Sidewalk gave it, straight up: Penny regularly steps away from the scene to "recharge his batteries," with tai chi and meditation. Not a drama, not a marketing ploy. Just a dude needing to chill.

And he could afford to do it because he never skated like he was managing a career. Chad Muska put it best: "It was almost like he didn't know he was doing anything special." Skin Phillips, ex-editor of Transworld, added that he never realized the impact he had on skating.

That’s the paradox. Other pros built a presence. Penny dropped parts. When he came back, he had nothing to catch up on: his style never aged because he wasn't chasing trends. He earned that 2011 ranking with what nobody can copy, not with what he did most often.

Today, in France

In 2023, he was inducted into the Skateboarding Hall of Fame. The induction text, signed by Don Brown, speaks of a "fresh face from Oxford" and his "iconic win at Radlands." And a final line, which concerns us: he lives in France today, and often skates in Spain.

His influences? He cites Daewon Song, Rodney Mullen, Danny Way, Chad Muska, and Steve Caballero. To dive deeper into those who crossed his path, check out our features on Andrew Reynolds and Eric Koston. And if you want to ride the same brand as him since '93, Flip decks are still around.

Which one is your part of Penny? Hi-5, Menikmati, or Sorry? Let us know in the comments ↓