Revisiting the Golden Era of Skate Videos

A nostalgic look back at iconic skate videos and their impact on music and culture.

Venice Skatepark is a 10 min walk from my place. Now that my partner has picked up roller skating (next to the Skatepark), I’m spending more time there than ever. I’m finding myself spending a lot of time there watching and appreciating the individual styles but also just enjoying the art and culture of skateboarding. It reminds me of a time in my life when I watched skating (& wrestling) more than I watched any other sport. 

Before I get into this, it’s worth noting. I’ve owned skateboards and done it here and there but never called myself a skater.

- Have I ever landed a kickflip? Probably not when actually moving at speed.

- Did I play a lot of Tony Hawk? Who didn’t?

- Have I ever ollied downstairs? Maybe one or two. Definitely not three.

- Did I love watching skate videos? Absolutely.

- Could I roll from point a to b, to go grab some food or beers? I could.

- Could I do any of the tricks in the videos? Absolutely not.

Growing up, my brother and his mates all skated. They would come over, somebody would bring a VHS of the latest skate video and then go skating. These videos not only made me appreciate the art of skating and individual styles, they also introduced me to music that I’d never heard before. 

I’m very fortunate that of the 10 or so video tapes we had at home, at least 5 of them are considered some of the greatest skate videos of all time.

Take an extended coffee break at your desk, away from slack and away from your corporate emails and go down memory lane with me.

Shorty’s Fulfil the Dream (1998)

My brother and my favourite video and team of all time.

This was Chad Muska’s first video since leaving/getting fired from Toy Machine and I think it was the best move for all parties. Chad was the heart & soul of Shorty’s and hand-picked the team. The footage is all extremely raw and there are no special effects but this video is close to perfect. There is no real storyline, just good old-fashioned technical skating. An unforgettable soundtrack as well. 

All skaters do some of their best work in this. This is often on YouTube start to finish in the background as I potter around the house. I love the soundtrack, from everything from the GZA to Grave Digger and Cat Stevens, this video has it all. Bonus points for also having the originals with lyrics.

Favourite scenes/tracks:

8:25 - My favourite track on this video. My brother and I looked for this song for a good decade and only ever found the ripped instrumental which has the skate noises in it. Great skating from Aaron Synder as well.

10:41 - Toan Nguyen, seems like the type you want on a skate team. Skating to the GZA Pass The Bone, delish.

18:30 - This part gives me (and a lot of the YouTube commenters) goosebumps. Again, one of my first introductions to Cat Stevens and nostalgia does all the right things for me.

30:00 - the main man himself.. The Chad. One of the best skate parts of all time.

To better understand the impact, have a squizz at the YouTube comments.

Girl, Yeah Right (2003)

Directed by the one and only Spike Jonze. 

This video used technology that no other team was using at the time. The ultra-slow motion camera combined with the special effects using green screen - this just hadn’t been done for skating. So in terms of pushing boundaries and being creative, this is very close to taking the cake. 

It also has a cheeky cameo from Owen Wilson (33 mins) and this is post-Zoolander, once he was a global star.

The tribute to Keenan Milton at the start is very classy and well done.

Favourite scenes/tracks:

10:16 - This is such an iconic scene and concept - probably one of my favourite of all time. My first introduction to Jurassic 5. Also a great way to get all of the team involved. 

35:00 - Talib Kweli - Get By(instrumental).. my first time hearing this and definitely not the last. It’s appeared in multiple of my Spotify wrapped since that became a thing.

42:50 - Young P’Rod looking like a Vinny Chase stunt double. Back to back Nas instrumentals whilst skating in something other than nikes is also very cool. (He was recently asked about this scene and its impact, watch that here.)

56:12 The invisible deck. This is the green screen technology I was talking about. If you are going to watch any of these, definitely watch this one. This scene back in 2003 was mind blowing and with this song(John Frusciante - Murderers) over the top, say no more.

71 mins of an excellent video.

“The Chocolate Tour” 1999.

“It's the summer of 1999 and what the Chocolate team thinks will be a normal skateboarding tour across the USA, turns into a race against time with a new set of rules… Brushes with the law, forgery and fraud are just a few of the startling mis-adventures the Chocolate Brotherhood have on their way to saving the only other family they’ve ever known – the Girl team. Armed with a healthy respect for their elders, and a strong sense of camaraderie, the Chocolate team faces the overwhelming responsibility of being the last hope for their Girl brothers… or are they?”

The concept of this is great. The old man makeup. The nursing home. The scams, it’s what you want as a 10 year old kid. 

Directed by Spike Jonze.

Favourite scenes/tracks:

5:11 - Mike York skating to Straight outta Locash. 

25:15 - Keenan Milton is great in this. RIP.

29:57 - The introduction of Gino Iannucci’s part, in 2023, is cheesy and hasn’t aged super well but in 1999, extremely cool. Also skating to the instrumental of one of my favourite tracks by the GZA, delish.

32:01 - Probably no better way to finish this video than Stevie Williams skating to Big L- very fitting for the guy who founded DGK (Dirty Ghetto Kids). His style as a skater is timeless. He also had so much time and made it look way too easy. His 360 flips are something else.

Birdhouse The End (1998)

This video reportedly cost $1 million dollars to make and in 1998, that is a lot of jam donuts. It feels very over the top and Hollywood but hey, it was produced by Tony Hawk. For the cost of this video and level of production, it probably could have used a more cohesive storyline but all in all it’s worth watching.

An introduction of a random orangutan in the team video was the first I know of a gimmick type feature and it works.

Favourite scenes/tracks:

7:05 A very very young Andrew Reynolds. He kills this. And I think this led to me eventually buying his signature Emerica sneakers.

13:30 - Steve Berra. I never really understood this part, I guess it’s to do with him running away from his demons. But I do love the juxtaposition of skating to what sounds like the score from a horror film. 

24:58 - by far the best scene in the video. Queen - Under Pressure, featuring Heath Kirchart & Jeremy Klein night skating in suits over building signage, service stations & bus shelters. This part feels like where the Tony Hawk games drew a lot of inspiration from. 

Speaking of, this scene is followed by the man himself doing some things only he could do.

Almost - Round 3..

Now this one nearly didn’t make the cut..  It came out as we started to learn and love other things in life.. but that being said, it’s a good old fashioned skate video. Slightly different to the previous Round series, this features the team ‘competing’ against each other. Great music, a great team and even better skating. 

Favourite scenes/tracks:

These are so good, somebody has gone to the effort to create individual videos so lucky you.

I was only going to post the Daewon Song clip, as his effortless style was one of my favourites to watch.

But then I rediscovered the Rodney Mullen part. What the hell is he even doing with this board? I couldn’t do this shit on a tech deck.

During this era, when Napster and limewire were the Spotify, it was skate videos where we found music. I’d love to know how it all worked. I doubt there was much more to it than, “I love this track and want to skate to it.” The skating is what made the video good, the song selection is what made it iconic. For Rodney Mullen going from The Clash into Massive Attack is something else.  

I’ve missed a good 15 + years of pro skaters, but the comment section tells me that nobody can even come close to being as tech as the one and only Rodney Mullen. Those dark slides, holy moly. 

Now let’s look at 15-year-old Ryan Sheckler. I feel he’s most known for his MTV days but damn he could skate. Just watch this clip to see how good he was. And again.. The Cure - Why Can't I Be You, stop that.  

Thanks for reading and I hope you have the time to go back and watch some of these videos. They also make for very good background viewing during pre-drinks, shout-outs to the BP, Tooraks finest.

Hayden