Simon Woodstock was born on April 23, 1974, in Riverdale, Bronx, New York, and his journey into professional skateboarding began during the early '90s. He quickly gained attention for his unconventional style and fearless approach. Simon was an original, falling somewhere between a pro skater and a clown - a rare breed that included legends like Lance Mountain, Harold Hunter, and Mike York. His skating was a mix of raw talent, humor, and full-blown creativity.

Simon Woodstock was known for his innovative tricks and antics which included:
Skimboard and Snowboard Setups: Simon pushed the limits by riding skimboards and snowboards as if they were skateboards.
The Clown Suit: Simon’s playful side extended to his wardrobe. He often rocked a clown suit while skating, adding an element of humor to his sessions.

Simon rode for 90s brand Sonic Skateboards and was featured in their ads.

Simon also rode for Madrid Skateboards during his pro career. In 2005, Madrid released the El Cochino complete deck—a giant skateboard with a kicktail and upturned nose. Locals loved it, and Madrid put them into limited production. Simon’s irreverent style perfectly matched the style and spirit of this unique deck.

His skating was featured in the 1993 Thrasher video titled "Need for Speed" and while he wasn’t a contest-focused skater, his influence extended beyond scores and rankings.

In a surprising twist, Simon found God and embarked on a new path.

Simon Woodstock: Thrasher "Need For Speed" Skate Vid Section

Simon Woodstock: Human Skateboards "Caught Clean 2: Radioactive Throw Up" Skateboard Video Section

Simon Woodstock and the Sonic Team in Switzerland 1995 Raw Skate Video Footage

"Memories of the beginning days with this visit of the inspirational Sonic Team consisting of Simon Woodstock and Nanda Zipp in Zurich. Filmed by my father. Those were the days!! Enjoy!" Deep Society

"Metal Mom" by Simon Woodstock: Big Brother "Boob" Skate Video Clip

"Metal MOM ! Love it , you just brought me back."

"What a privilege to exist in those times mate. I was a young teenager watching this. It all formed parts of personality and my sense of humour today. This is an amazing time capsule. Please keep posting these."

"So glad youre posting some of this footage. Absolutely sick, still."

"sick! loads of attitude. i miss those days. (i also remember this tune from 'dont try this at home')"

Ride Channel: Simon Woodstock's Story - Part 1

"Always been a fan of Simons, he always showed that skateboarding had no boundaries or rules and was about having fun! Much respect!"

"Everyone who knew what was up loved Simon Woodstock.."

"Simon Woodstock was so great to watch during that weird time in skateboarding. I remember whenever he would be in a 411VM we would just watch over and over the craziness that was Simon Woodstock. Thanks for the retrospective"

"Awesome documentary, skateboarding needs more people like Simon "

"Simon was awesome back then. Some dudes were trying to be all gangster at the time, or act like badasses. Simon would show up in a clown suit doing weird tricks. It was a nice reminder that we were all just kids trying to have fun. Thanks Simon!"

"I remember watching him on VHS tapes back in the day dude is fucking sick man doing tricks on some of the most outrageous boards I've seen lol"

Ride Channel: Simon Woodstock's Story - Part 2

"That was great to watch. Skateboarding and the world in general need more people like Simon.  Shine on you, crazy diamond."

"Skateboarding hardly has anything to do with actual skateboarding. just being in the kroger parking lot at night with all the homies is the greatest feeling ever!"

"That guy is a legend. Made us try things silly tricks we never saw before. major props from Montreal!"

"He has the soul of a true skater!"