The early 2000s were a straight-up golden era for skateboarding videos if you ask me. It was a time when full-length VHS and DVD releases were truly everything. These videos influenced our style, helped us progress, and introduced an entire generation to some of the most iconic skateboarders, timeless tricks, soundtracks and spots of all time.
From the heaviness of Baker and Zero videos to the magic of early Transworld SKATEboarding videos to Alien Workshop, Habitat, Emerica and so many more, these 13 videos truly changed my life and still resonate with me today.
As always, these are just my opinion—in no particular order—and I know there were plenty of other gems that dropped during this era as well. But between the years 2000–2005, these videos were on constant rotation on my TV and honestly, still are to this day. Let's take a roll down memory lane.
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You could argue that Photosynthesis was as much of a skate video as it was a full-on experience. This video helped define an era with its artsy, out-there vibes, raw street skating, an absolutely timeless soundtrack, and that unmistakable Alien Workshop aesthetic that we've all grown to love.
Jason Dill, AVE, Kalis, Freddy Gall, Wenning, Getz, a super young Mark Appleyard, Dyrdek before his MTV fame! Every part hits hard, and the editing ties the entire video together perfectly. Joe Castrucci’s direction, classic VX1000 footage, an almost eerie, dreamlike vibe ... yeah, this video will go down as one of the best. And the orange VHS tape? Pffft. Game over.
Yellow VHS tape. Johnny Rotten narrating the whole thing. Arto Saari literally almost dying. That trippy Tom Penny section. Geoff Rowley! The intro itself provides a certain kind of energy that you just don't always get. There was no weak link in the video, and even though I'm almost embarrassed to admit that I'd fast-forward Rune Glifberg and Alex Chalmers' parts when I was a kid, those are both some of my favorites these days.
This was such a golden age of Flip Skateboards and Sorry has truly stood the test of time. I watch this one all the time still, and I still get just as stoked as when I was a bratty 13-year-old kid. A mandatory addition to this list.
Some skate videos stand the test of time, and some change the game completely—Yeah Right! is one of those. The Crailtap crew has always set the bar high when it came to skate videos, but this one? Yeah, next level.
From the mind-blowing green screen effects to the legendary invisible boards montage to the skating itself, they somehow pushed progression in every direction at once—tricks, filming, editing, everything. Dope soundtrack? Check. Posi vibes? Check. Pure gold.
Honestly, just thinking about how much Yeah Right! shaped my childhood almost makes me emotional. Forever in my Top 3.
The same way Yeah Right! took things to the next level, The DC Video did the same, but in a slightly different way. This was a pure skateboarding spectacle. Big budget. High impact. Straight-up iconic. It was a true product of the era. With Danny Way's timeless Mega Ramp section, AVE’s raw street destruction, Stevie, Kalis, Lindsey Robertson and Ryan Smith in their prime—little Greg Meyers!? I'm truly just scratching the surface here. The entire lineup was stacked.
And I mean, the iconic Rob Dyrdek and Big Black skit speaks for itself. That opened up so many doors for those two, but as a kid, it was the most entertaining little segment ever. This is truly a legendary video. In fact, I'm gonna put this whole thing on hold and watch it right now.
Emerica's This Is Skateboarding is an absolute classic. It was one of the first times we witnessed the editing magic and creative direction of Jon Miner (and of course Mike Manzoori), and it sort of set the tone and theme for all the Emerica videos that followed.
Reynolds, Herman, Spanky, Heath, Leo—this video just feels like skateboarding. It's raw, fast, and full of energy from beginning to end. Even Darren Navarrette had a mini part! That said—Heath Kirchart’s part? Legendary. Reynolds? Timeless. The soundtrack? Obscure, chaotic, perfect. It’s simply the kind of skate video that gets you hyped to skate the second it starts. If you grew up on this one, you already know. If not, do yourself a favor and watch it—this really is skateboarding.
I mentioned this list wasn't in any particular order, but if it was, Dying to Live would be way up there. This was the first skate video (VHS) that I ever bought with my own allowance money as a 12-year-old kid who was becoming obsessed with the culture.
Zero videos will always hold a special place in my heart. Dying to Live is just a classic, hard-hitting Zero video—raw, brutal, no-nonsense, no filler. Just clip after clip after clip. That tight zero fisheye? Absolutely legendary! The soundtrack? Still listening to all these songs to this day!
Dying to Live really set the standards pretty high when it dropped. The handrails were bigger, the spots were terrifying and the entire team was all-or-nothing. Shoutout to The Chief for blessing us with this banger. Another unarguable Top 3 for me.
Hey, I'm not trying to play favorites here, but it'd be absolutely insane not to have Sight Unseen on this list. Cardiel’s part alone is the stuff of legend—pure, no-nonsense, high-energy destruction on four wheels. Heath Kirchart skating to "Knights in White Satin" is literally one of the gnarliest video parts ever.
Then of course, we got Dustin Dollin, Henry Sanchez, Tosh Townend—the whole squad went off. But it was the editing and cinematography that also made it so timeless, and even decades later, it still hits super hard. I watch it all the time still! Gotta love that golden era of TransWorld SKATEboarding videos.
Whoops, maybe I am playing favorites! Nah, but again, it would feel super weird not to have In Bloom on this list. It's a little more personal to me than Sight Unseen, I will admit that. I bought this VHS the same day I bought Dying to Live, and I'm not kidding when I say I remember it like it was yesterday.
When it came down to it, though, In Bloom was the ultimate coming-of-age skate video—a perfect snapshot of the next generation right before they blew up. P-Rod, Evan Hernandez, Chris Cole, Mikey Taylor, Tony Trujillo, a young, rail-chomping Trainwreck—every part epitomizes that early-2000s rawness. Classic TransWorld vibes with all the voiceovers in their intros, too.
This one introduced a ton of us to "the future" of skateboarding at the time and still holds up decades later. Maybe you've heard of some of these guys? ;)
Toy Machine’s Good & Evil was the perfect concoction of heavy skating, classic Toy Machine weirdness, and top-tier cinematography. Kevin Barnett was one of those filmers that everyone ended up copying after a while, and some of the clips he filmed in that video are still gawked over to this day.
The team was so stacked at the time and even Ed Templeton was still out there stacking clips in the streets. It had all those classic Templeton animations peppered throughout, a soundtrack that an entire generation obsessed over and it was genuinely just a proper look at this golden era through the lens of the Bloodsucking Skateboard Company known as Toy Machine! Revisit this one if you haven't in a while. So good.
Raise your hand if you remember that classic Corey Duffel slam in the intro? Foundation's That's Life was a straight-up hammer fest if you ask me. This video was extremely heavy. The entire team brought it, including a young Leo Romero in what you could argue was one of his breakout parts.
Duffel, Fowler, Strubing, Schmizu, Stehr—it was the perfect snapshot of the "hesh" side of the early 2000s and had an entire generation of kids wearing pants as tight as The Ramones, ripped, striped shirts, weird hats and bragging about how greasy and nasty their hair was! (Guilty!) It was the type of video you'd put on before you went skating because it had an insane energy to it. Still does. An absolute classic! I can hear that intro song right now.
Like Photosynthesis, Habitat's Mosaic showed kids like me a different side of skating. While I was busy watching Zero videos and stuff like That's Life, videos like Mosaic introduced me to a more creative, stylish, refined side of skateboarding. The spots, the music, the different styles.
Mosaic was the perfect mix of artsy filming/editing and superior skating. With classic creative direction from Joe Castrucci and parts from dudes like Danny Garcia, Stefan Janoski, Fred Gall, and the rest of the squad, it was—and is—truly a thing of beauty. Classic VX1000! Tasteful B-Roll! The perfect soundtrack! This banger still holds up today. Habitat videos always have their own vibe, and Mosaic definitely helped set the standard.
Proud to say I still have my white VHS tape to this day!
Baker 3 is obviously a mandatory addition to this list. When this video dropped, everything changed. The hijinx, the skating, the partying—Baker videos always had a raw, unique vibe of their own, but Baker 3 really took things to the next level. It was literally a cultural milestone, as far as I'm concerned. Pure savages!
It was hectic and gave us all such a raw, legitimate look at street skating far beyond just the tricks and clips. The Baker team was legendary during this era, and every single skateboarder on the planet wanted to be a part of it. In fact, ask a room full of skateboarders who grew up in this era what their favorite skate video is, and I'd guarantee the majority would say Baker 3.
BAKER, BAKER, BAKER!
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