Vol. 13: And My Old Skateboard
There was a period in the early 1990s where it felt like the walls between music scenes started collapsing.
Skaters were listening to hip hop. B-boys were wearing flannel. Metal heads were showing up to house parties where Cypress Hill, Pearl Jam, Beastie Boys, and Rage Against The Machine somehow all made sense together.
At least that is how I remember it.
The Summer of 1991 through the end of 1992 remains one of my favourite periods in music history. Looking back now, it almost feels impossible how many important albums arrived within such a short stretch of time.
Pearl Jam and Cypress Hill both released their debuts in August of 1991. Nirvana followed with Nevermind that September. In 1992 alone, there was Dr. Dre’s The Chronic, Rage Against The Machine’s self-titled debut, Beastie Boys’ Check Your Head, Alice In Chains’ Dirt, Pharcyde’s Bizarre Ride II the Pharcyde, Das EFX’s Dead Serious, Tool’s Opiate, Ice Cube’s The Predator, and Fu-Schnickens’ F.U. Don’t Take It Personal.
Looking back, it felt like the soundtrack to a cultural collision.
Skaters, b-boys, punks, and metal heads all seemed to be borrowing from each other at the same time. The old cliques still existed, but the lines between them started blurring.
House parties no longer felt as segregated.
Music became less territorial.
And skateboarding quietly sat in the middle of all of it.
When Skateboarding Became a Music Discovery Engine
I recently sat down with my old friend Brad Hainschwang, a longtime skateboarder and founder of Gnar Optics, to talk about the relationship between skateboarding and music, and how skate culture quietly became one of the most influential music discovery systems of its era.
Before algorithms started feeding people playlists, skateboarders discovered music differently.
Through skate videos.
Through older kids at the skatepark.
Through local skate shops.
Through mixtapes.
Brad explained it simply:
“Skateboarders move around a lot. You meet different people, you hear different music when you’re skating in the streets, so of course you’re gonna have influences from all over. The people you skate with have different backgrounds than you. Skaters take influence from everything, so music would kind of follow that as well.”
That line stuck with me because it perfectly describes what skate culture often felt like from the outside looking in.
It was one of the few places where musical boundaries felt less important.
You could hear punk music one minute and underground hip hop the next without anyone treating it like a contradiction.
That overlap mattered.
Especially during an era where music scenes were still heavily tribal.
Hesh vs. Fresh
Brad laughed when talking about the early 2000s and the way skate culture itself started splitting stylistically.
“There was a time in the early 2000s where there was ‘Hesh vs Fresh,’ but it was more in a fun way. You had guys with tight pants and you had people with baggy pants and triple extra-large t-shirts. It was an interesting time. There was definitely camps, but for the most part everyone got along.”
That period really did feel like a visual tug-of-war between punk influence and hip hop influence.
One skater looked like they just stepped out of a hardcore show. Another looked like they came directly from a rap video on MuchMusic.
And somehow both identities comfortably existed inside the same skatepark.
To outsiders, those worlds may have looked completely incompatible.
Inside skate culture, they often overlapped naturally.
The Local Skate Shop Was Part Record Store
One of the more interesting things Brad mentioned was how influential local skate shops became when it came to shaping musical taste.
“The local shop definitely influenced music on people. Whatever they were playing in the store or if there was a new video. Some stores even did mixtapes that they would sell to the kids, so you would have a mixtape of all the newest songs that were in skateboard videos.”
That detail says a lot about how music discovery worked before streaming.
A skate shop was not just somewhere to buy boards and wheels.
It was a cultural filter.
If someone behind the counter played a certain band enough times, eventually kids started listening to it. If a song appeared in a skate video, somebody would eventually ask what it was. Mixtapes started circulating. CDs got copied. Entire scenes spread this way.
Skateboarding did not just reflect culture.
It distributed it.
My One and Only Skateboard
The funny thing is, I was never really a skater myself.
Not for lack of trying.
I remember my dad taking me to Markville Mall sometime in the early 1990s to buy my first and only skateboard.
The store was called Collegiate Sports, one of those classic pre-big-box sports stores that seemed to exist in every suburban mall during that era. Back then, Markville still had the indoor streams, the Wizard’s Castle arcade, and the old Famous Players theatre.
The skateboard itself was an Excalibur.
I practiced in my driveway for maybe two weeks.
Mostly I remember falling.
A lot.
Eventually I gave up, mainly because I was too immersed in writing raps and trying to get my group at the time, Phreekz Uv Naychur, noticed by record labels.
But even though I never fully entered skate culture myself, I always admired skaters.
Especially their willingness to repeatedly destroy their bodies simply for the love of it.
Watching my friends skate the high school parking lot was always entertaining to me. The music, the clothes, the boards, the personalities, it all felt connected somehow.
Looking back now, maybe that is part of what made skate culture so influential. Even people standing nearby still absorbed pieces of it.
Check Your Head
There was one album from that era that hit me harder than almost anything else.
Check Your Head by the Beastie Boys.
It is difficult to explain to younger listeners just how influential the Beastie Boys felt during that period, especially for skaters.
Their music sounded like multiple worlds colliding at once.
Punk.
Hip hop.
Hardcore.
Funk.
Dusty samples.
Live instruments.
It felt messy in the best possible way.
And like a lot of teenagers during that era, I absorbed all of it.
I started dressing differently. Even dyed my hair.
Ad-Rock in the “So What’cha Want” video basically became my school uniform blueprint.
Looking back now, it seems funny that an album could influence somebody’s identity that heavily, but music absolutely did that back then.
Especially when you were young.
And especially when skate culture amplified those influences visually.
The Songs That Stay Attached to Skateboarding Forever
Sometimes music becomes attached to skateboarding in strange ways.
Not because the song was intentionally part of skate culture, but because it accidentally became connected to a memory.
Brad told me there is one song he still permanently associates with skating:
“A song that will forever be stuck in my head would be Journey’s ‘Any Way You Want It,’ and the reason for that is one of my old roommates would pass out on the couch playing the menu part from the Almost skateboard video, and that was the song that was on loop.”
That story perfectly captures how weirdly personal music memories become.
Sometimes a song reminds you of a place.
Sometimes a person.
Sometimes a skateboard video menu looping endlessly at 2 a.m.
And decades later, the connection still survives.
Before Algorithms
One thing that kept coming back to me during my conversation with Brad was how different music discovery once felt.
Today, streaming algorithms feed people recommendations endlessly. Music arrives personalized, optimized, and isolated.
Back then, discovery often happened socially.
- Somebody at the skatepark played it.
- Somebody made a mixtape.
- A local shop kept replaying it.
- A skate video introduced it to you.
- A friend’s older brother owned the CD.
The process felt messier, but maybe more memorable too.
Skateboarding became one of the places where all those influences collided together naturally.
Punk kids discovered rap.
Hip hop fans discovered hardcore.
Metal heads discovered funk samples.
And somewhere in the middle of all that, entire generations quietly built their musical identities.
And My Old Skateboard
Years later, a lot of those boards are gone.
The shoes changed.
The scenes evolved.
Some of the skate shops disappeared.
But the music stayed attached to the memories.
That may be the real connection between skateboarding and music.
Not just influence.
Not just style.
But memory.
The soundtrack becomes inseparable from the time period itself.
You hear certain songs and suddenly you are back at the skatepark again. Back at the house party. Back flipping through CDs at the local shop. Back watching skate videos in somebody’s basement while arguing about music and fashion and what counted as “real.”
And for a moment, your old skateboard is still leaning against the wall nearby.
Wear the Story
This volume also inspired a new limited shirt design, And My Old Skateboard, available through the Music Over Money collection. As with the Music Over Money tee, $5 from each shirt will support MusiCounts and their work helping young people across Canada access music education.
Because this story was shaped in conversation with Brad from Gnar Optics, the collection may also include a few selected pieces from Gnar that fit naturally with the skate and music culture behind this volume.
View the Music Over Money collection
Companion Playlist
A playlist inspired by skate videos, local shops, punk, hip hop, and the songs that somehow get permanently attached to the memories.