Andrew Reynolds: A Skateboarding Legend Redefining Street Skating

Explore Andrew Reynolds' inspiring journey from a skateboard-loving kid to a street skateboarding icon, shaping the sport's future.

An epic tale of perseverance, passion, and pushing boundaries—who could it be other than the skateboard guru himself, Andrew Reynolds? Haven’t you heard of him? Well, let me tell you, you’re in for a treat. Andrew Reynolds is etched in golden letters in the history of street skateboarding. His journey is nothing short of inspirational, with his roots running deep from a small town to being hailed as a modern skateboarding icon. This is your backstage pass to the life and times of the literal boss of skateboarding, Andrew Reynolds.

Where did Andrew Reynolds’ skateboarding story begin?

Born on June 6th, 1978, in Lakeland, Florida, Andrew Reynolds resided primarily with his mother following his parents’ divorce. With humble beginnings in the insurance industry, his parents couldn’t have imagined the epic heights their son would attain. As a kid, he was captured by the magic that a skate video called Psycho could ensue.

Image of andrew reynolds from an interview.
Image of andrew reynolds from an interview.

This happened on a sunny day when young Reynolds lounged around, watching MTV with his sister. It was love at first sight for Andrew and skateboarding! This fascination led him to receive his inaugural skateboard as a birthday gift at the tender age of nine. Unlike an overly invested soccer mom, his mother allowed him to explore this new love.

My favorite complete skateboard (at the moment):

Enjoi Whitey Panda Complete Skateboard

Andrew reynolds: a skateboarding legend redefining street skating | 61vn95mf7ql. Ac sl1184 | skateboard salad
My favorite complete skateboard (at the moment):

Enjoi Whitey Panda Complete Skateboard

I had my board stolen a few years ago and was forced to quickly replace it with a complete. I got one with an Enjoi deck and loved it so much that I still buy the Whitey Panda deck each time I need a new deck. This complete with budget-friendly, beginner-friendly parts, but I still swear by it.

Was Andrew’s first encounter with street skating a turning point?

Often, you encounter a couple of friends who infect you with their passion, causing a significant stance change. This was pretty much the case with Andrew when he met two skater kids named Clay and Robbie. While they were mostly inclined towards street skating and Andrew had a knack for ramps, it didn’t hinder their friendship.

Despite being older than him (17–18 years), these guys spent countless hours at his place. Their influence was so prominent that the mini ramp in Andrew’s backyard was soon forgotten, replaced by an insatiable love for street skating. This new flavor of friendship led to the beginning of something exciting.

Their influence was so prominent that the mini ramp in Andrew’s backyard was soon forgotten, replaced by an insatiable love for street skating.

Their camaraderie evolved to the point where they decided to create home videos of their skateboard adventures. This garnered much attention, and Andrew eventually crossed paths with a local skate shop, landing his first sponsorship with the Cove shop.

Apart from the front-row seat to his skateboarding exploits, these videos were instrumental in landing his sponsorship deal. Here’s what Andrew said when he got signed: “I thought I was like the biggest deal ever. Like, who’s giving away a free complete to a little kid? This is insane!”

How did Andrew Reynolds make it to the pro skateboarding league?

Andrew’s growing prowess with the skateboard didn’t go unnoticed for long. In a twist of fortune, at the age of 14, Jake Montez, the first pro skater Andrew ever met, introduced him to the manager of the GNS team, a team Andrew aspired to be on. Whatever they discussed seemed to work miracles because, by the end of the competition, the manager extended an offer to sign young Reynolds.

Life took a turn for Andrew again when he met Felice Santos, who provided guidance on his path to becoming a pro skater. Crossroads emerged when Tony Hawk started Birdhouse in 1992, and Andrew signed off on them. But Santos remembered Andrew and talked with Tony Hawk about adding him to the team.

Being on the Birdhouse team changed things; this experience turned Andrew into a pro skater before graduating High School. With skateboarding greats like Tony Hawk, Willie Santos, Ocean Hall, and Jeremy Klein on the team, Andrew was in excellent company.

Image of a skater doing some skateboarding tricks.
Image of a skater doing some skateboarding tricks.

The journey to fame: Andrew Reynolds and birdhouse

After moving to California, Andrew was extensively featured on Birdhouse’s skate videos, which were a hit, specifically Union Wheels: Right to Skate, Birdhouse Projects: Untitled, and Ravers. These projects were unique in the sense that they were completely unscripted. The team would drive around, spot something cool, and just skate!

However, high school became somewhat of a drag for Andrew, especially during his last year. Excelling in skateboarding also meant that he had already turned pro for Birdhouse. Understandably, the conventional route to school seemed a tad uninspiring to him. His mom ensured he finished school and only had to confiscate his skateboard a couple of times to make sure of it.

Together, their group called themselves “The Piss Drunks.” They were some of the most sought-after skaters of the time, shredding and ruling the ramps while living their lives to the fullest.

Inspired by legends like Chad Muska and Tom Penny, Andrew started skateboarding with friends like Jim Greco, Erik Ellington, Ali Boulala, and others after moving to California. Together, their group called themselves “The Piss Drunks.” They were some of the most sought-after skaters of the time, shredding and ruling the ramps while living their lives to the fullest.

This potent mix of talent and unabashed individuality put out the 411 videos, marking Andrew’s steady climb toward skateboarding’s hall of fame. It was undoubtedly clear that Andrew was getting really good, as showcased by his willingness to ollie between 4-wheel drive and 4-1-1.

What are his skateboarding highs and lows?

In the midst of such an impressive career, it wasn’t all rosy for Andrew. The constant pressure and temptations led to his rock-bottom phase, characterized by his move out to Huntington Beach, California. He lived a jarring lifestyle centered on skateboarding and substance abuse.

However, watching Andrew maneuver his life and skateboard, it is evident that the former, as rough as it may have been, couldn’t tamper with his devotion to the latter. He continued to stun the world with his killer skateboarding style and tricks. Named “The Boss” by his peers, Andrew defined a new era of skateboarding, inspiring many future icons like Kate Urcilla.

My take on Andrew Reynolds

I must remind you that while I’m no skateboarding whiz, I am thoroughly stoked by Andrew’s journey. From a quiet kid in Florida to an international skateboarding star, his trajectory is enlightening and motivating. His ability to rise above personal challenges while maintaining his skateboarding passion made a real impression on me.

“Success is not final, failure is not fatal: It is the courage to continue that counts.” – Winston Churchill

It’s a living testament that echoes the age-old philosophy: when you stumble, get up and keep moving. If you’re interested, check out some of the most legendary skateboarding fail videos to see how falling leads to triumph in our world.

If you are a visual learner, check out the video below from YouTube.

Frequently Asked Questions (FAQs)

Engaging in a skateboarding journey, especially when it’s street skating, can lead to many questions. Here, I’m addressing some of the more frequently asked ones to enhance your understanding while also feeding your curiosity about the world of street skateboarding.

What inspired Andrew Reynolds to start street skating?

Andrew Reynolds was drawn to skateboarding at a young age when he saw a skateboard video commercial on MTV. One of his birthday gifts, a skateboard, sparked a journey that led to him becoming one of the most respected names in street skateboarding.

His switch to street skating came when his friends inspired him to try it. They skated, filmed, and had fun, which Andrew truly embraced, giving him the nickname “The Boss.”

Can anyone start street skating at any age, like Andrew Reynolds?

Absolutely. Skateboarding isn’t bound by age; you can master it at any age. However, as with any activity, the earlier you start, the better you can imbibe the skills and techniques. Some notable skaters, like Andy Anderson and Andrew Reynolds himself, began young, but nothing stops you from starting now. It’s definitely harder later in life, but don’t let that discourage you.

Is street skating allowed everywhere?

It depends on local laws and regulations. Certain areas prohibit skateboarding due to the risk of accidents and property damage. It’s essential to consider local laws before street skating in public areas, which might lead to fines or impoundment of your board. To avoid this, you can check out these kinds of skateboarding trends for alternatives.

Is Andrew Reynolds still skateboarding?

Absolutely! Even decades later, Andrew Reynolds still actively participates in the skateboarding scene, shredding it and inspiring generations of skaters worldwide. The legacy of Andrew Reynolds is ever-thriving, and he continues to be an icon in the realm of street skateboarding.

Final thoughts

Andrew Reynolds’s journey from a suburban kid in Florida to becoming a global skateboarding icon is a testament to the fact that passion blended with persistence eventually leads to mastery. His story reiterates how embracing your calling, as offbeat as skateboarding, can lead you to unparalleled heights. Mastering his craft against all odds, he became a successful skateboarder and an incredible mentor to enthusiasts like Kate Urcilla.

Can you, too, groove to the rhythm of passion and take the road less traveled, as Andrew did? And did I cover everything you wanted to know? Let me know in the comments section below. I read and reply to every comment. If you found this article helpful, share it with a friend, and check out my full blog for more tips and tricks on skateboarding. Till next time, keep skating and keep smiling!

Key takeaways

This article covered the life and career of street skateboarding icon Andrew Reynolds. Here are some key takeaways:

  • Andrew Reynolds developed a passion for skateboarding at age nine after watching a skate video commercial on MTV.
  • His journey to professional skateboarding was marked by a significant shift from ramp skating to street skating.
  • Reynolds’ first sponsorship deal came from showcasing his tricks on home videos with his friends.
  • Andrew played a formative role in shaping the careers of many future skateboarders.
  • Throughout his journey, Andrew Reynolds balanced fame and personal growth, which continues to symbolize his legacy in street skateboarding.

Helpful resources

Steven Portrate
Written by Steven Sadder, Staff Writer

Hey! I'm Steven, a lifelong skater, and proud New Yorker. I’ve been skating since I was a teenager. I may be a bit older now, but I'm not slowing down. Follow me for skating tips and latest gear reviews.

Nick eggert.
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