Tom Penny (born 13 April 1977) is a professional skateboarder from Abingdon, Oxfordshire, United Kingdom (UK). As of January 2013, Penny is sponsored by the Flip skateboard deck brand and his Cheech & Chong signature deck is one of the brand's highest-selling deck products. Tom Penny is widely considered one of the greatest skateboarders of all time.
Penny was born in Dorset, England, UK and grew up skateboarding in Oxford, England, UK. He attended the Dragon School. Penny has described his early years skateboarding in Oxford:
When I first started skateboarding in Oxford, England, there were not so many skateboarders—there were just a few skateboarders that I grew up with. There were no magazines, no skate shop, and we had no vision of the outside world of skateboarding; so, people who influenced me when I was younger, growing up, would be the friends that I grew up skateboarding with: Justin Parker, Erin Chalice, Pete Crucioli and Thomas Kilpatrick.
Penny was first discovered and sponsored by Mon Barbour, owner of SS20 skateshop in Oxford—Penny was sponsored by SS20, an arrangement that continued after he moved to the US. Penny gained coverage in UK skate magazines, including RAD and Skateboard, and was featured in videos such as Rollersnakes 540 and 720.
Following the initial coverage that Penny received, he was soon spotted by Flip co-owner Jeremy Fox and was added to the Deathbox Skateboards team (Deathbox was later merged with Bash Skateboards and was re-branded as "Flip"). In 1993 Penny appeared in the inaugural Flip video The Long Overdue, alongside Geoff Rowley, Alex Moul, Andy Scott and Rune Glifberg—the video was made by Goff.
In 1993 Penny made his first international video appearance in 411VM's "Issue 2" and was featured in a "Wheels of Fortune" segment—Penny was 16 years of age and the segment features footage from the Radlands Skatepark in Northampton, UK. At the age of 16 years, Penny was sponsored by Flip, Independent, Droors, Union and SS20.