The Top Four Most Underrated Transworld Skateboard Videos

When it comes to Transworld skateboard videos, every skater who was paying any sort of attention during Y2K knows that the Ty trifecta (Feedback, The Reason, and Modus) is untouchable – both in terms of cultural impact and raw emotional power. The nostalgia is real and justified. But there are other TWS giants that loom large in our collective memory and hold comfortable seating in skateboarding’s Criterion Collection Sight Unseen may not have been a Ty joint, but Jon Holland didn’t miss a beat. Best video part ever? Possibly. (Who? Heath, duh.) 

The goal here isn’t to wax romantic about the same old familiar skating that we’ve all been going on about for years (I too still fawn over Carroll’s line at the SF library, but it’s hardly news). Instead, let’s acknowledge that the TWS canon is deep, and let’s highlight some of their excellent, less discussed full-lengths.

In putting this list together, let’s also acknowledge that judging what’s “underrated” is no easy task, but we have to draw the line somewhere. So, let’s say that those four we’ve already mentioned (Feedback, The Reason,Modus, Sight Unseen) are off the list. Let’s also leave out In Bloom. It may not get quite the same level of reverence on Slap, who can argue with a video that had up-and-coming parts from P-Rod, Chris Cole, and Trujillo (and others)? Not exactly low key. Now that those five are out of the way, every other video is fair game.

Now, let’s dust off that VCR in your mom’s attic and hit the nostalgia button for the good ole days when every new skate video mattered deeply.

1. Videoradio (unofficial Transworld Skateboard video, 2001)

If you started skating in the past ten years, then watching crowds roar as a skater pops a nollie flip on a bank might leave you scratching your head. While our lives now are defined by connectivity, 20 years ago, there was no way to DM our favorite pros. That absence left a world shrouded in mystique. Out of this fog emerged figures – Muska, Jamie, Penny – whose impact, beyond just their skating and charisma, also grew out of our accompanying sense of wonder.

The video isn’t perfect. And, let’s be real, there are other TWS videos (ones that didn’t make this list) with stronger editing and music. Instead, Videoradio is a time capsule from an era of myths and legends – an era that isn’t coming back. And diving in means remembering when demo footage was enough to get us stoked or Muska had to run for safety from his fans. Of course, diving in also means remembering when pants were way too baggy. Or when flip tricks didn’t have to actually flip. Or maybe even when Chris Cole skated for…enjoi?

Look, it didn’t all make sense, and that’s part of the fun. But one generation’s heroes were at the height of their powers, and the next generation’s (Apples, Cole) were lining up. It just so happens that they were all in the van together, and Jon Holland and Greg Hunt were savvy enough to know that they needed to keep the cameras rolling – because we were witnessing something special.

*Side note: most proper kickflip noseslide ever?

2. Free Your Mind (Transworld Skateboard video #14, 2003)

After the In Bloom hype train in 2002, it’s easy to overlook the understated 2003 follow up, Free Your Mind. Whereas In Bloom had six full parts from the top up-and-comers, Free Your Mind took a more leisurely pace with only three parts, two of which were established pros. And whereas In Bloom concluded with Alex Gall, a guy who went by the name “Trainwreck”, skating to Slayer, Free Your Mind opened with the easy grooves of one of the more inspired (and reportedly expensive) song-to-skater pairings in memory – Drehobl and The Zombies’ “Time of the Season”.

Unbeknownst at the time, Free Your Mind also marked the final full Rob Welsh part. A premiere tech guru, Welsh also understood what much of Instagram seems to miss – that truly great skating is founded on how you look on your board when there’s no flip-in, flip-out or skatepark goofery to hide behind. It’s about the basics, and a noseslide, or even a three stair, is more than enough. And, of course, this video also marks the pinnacle Darrell Stanton part. One of the most natural people to step foot on a board in the aughts, perhaps no one since has been able to so thoroughly Gumby tricks (with one possible exception). Then, of course, there’s that move on Clipper.

Stitched together with lighthearted skits of taxi rides – skits that actually work, mind you – around a much less gentrified San Francisco, Free Your Mind is a lighthearted, tasteful video that has aged gracefully. Now, just imagine if that Gonz part had happened.

3. First Love (Transworld Skateboard Video #17, 2005)

Every one of the guys in First Love was the best at what they did. Shiloh Greathouse – creative, “comeback” skater (many TWS vids had a comeback part, but how many of those guys got first part?). Richard Angelides – tech, but not robotic. Omar Salazar – speed. Ryan Gallant – style and flick. And Leo – handrails, of course.

It’s difficult to argue with that lineup. Skater’s skaters, through and through. It’s also tough to argue with how hard they put it down (go visit those last two Omar spots in person and see for yourself). But what makes this video truly lasting is its ability to live up to its title. Just like skateboarding itself, this video is more than tricks – it’s essence is joy and simplicity. It’s about how it makes you feel. It’s that Shiloh push off the curb. It’s every single song perfectly matching the skater. It’s that the best line in the entire video is almost entirely flatground.

It takes little courage to be cynical. And ultimately, that’s not why you and I love skateboarding. We love it because we still get that same, simple joy that we got when we were children. Credit is due to the directors, Jon Holland and Jason Hernandez, for understanding this and, even more so, being able to communicate it through their art.

4. Duets (Transworld Skateboarding Video #30, 2018)

In 2018, Transworld videos were in a tough spot. 29 video deep, it was apparent to all of us, the longtime faithful, that we were approaching the end. Struggling under the increasing weight of web clips and the Insta scroll, TWS made several attempts to retool their video format, but there was just no way that a full-length video could have an impact, much less pay for itself, like it did in 2000. When video #30,Duets, was announced, we all knew the inevitable: 30 was far too clean of a number. This was the swan song.

Great things, by nature, come to a close. And when that time finally comes for the things that we love, we’re fairly accustomed to lowering our expectations. Well, expectations be damned. Joe Monteleone and James Buchmann recruited the skaters that we wanted to see (really though, they had us at “Tiago”) and put together a video that was both current and thoughtfully infused with TWS’s past – from the “look out for me” guy to the Built to Spill track (if you know, you know). While the skating was great, it’s likely that we will remember Duets for something more important – as a final note of celebration and an end worthy of one of skateboarding’s greatest video legacies.