Caswell Berry has been in the game for a minute. He had his first published skate photo in a magazine when he was 11. He rode for the Ventura's notorious Christian-themed board company "Renaissance" (As in "Born Again") when he was 13. Rode for Powell alongside Javier Sarmiento and Danny Wainwright in his late teens. Then joined Diego Buchierri, Billy Marks, Ed Templeton, Austin Stephens and the rest of the loyal pawns at Toy Machine right around the time he turned 20—appearing and turning pro alongside Ed's assorted sex toys in the '02 tour video Sucking the Life. But after changing teams three times in his first decade of sponsorship, since switching to the Panda in '04—Caswell has stood firm as a mainstay rider at enjoi for almost a decade and a half. Combining the comforts of living in his home town of San Jose with the convenience of it also being the Tiltmode Army's and enjoi's home turf—I checked in with Mr. Berry to gauge how he was growing into his role as a seasoned veteran.
Photos by Wes Tonascia

Ollie in. San Jose, CA. (click to enlarge)

Hey Caswell, what's new? What kind of side gig are you working?
I've been helping my buddy, he has his own furniture wood shop and works with re-claimed wood and metal. When he needs help he hooks me up with some work. I have another job on top of that one just to pay the bills. It's nothing super embarrassing or anything; it's just your basic job/job.

Does it feel liberating to have outside income? Just as far as being self-sufficient?
Yeah, sort of but it also sucks because all I do is think about skateboarding. I deal with a lot of square folks. The woodworking job is cool because I work with a buddy and we can just shoot the shit, listen to classic rock, and do our own thing.

Last time we talked was right before Tweak the Beef (2012). Can you give a flash summary of life since then? At the time you were suffering from vertigo.
I still deal with that on the daily. If I sleep on my back, which I tend to do in the mornings then I get dizzy. Sometimes working with my buddy, if I need to drill some holes underneath the bench or something, I get super dizzy. It's just a weird positional thing. But since 2012, basically my life has been injury [laughs.] All my life skating I just had minor ones. But since '12, I've had three surgeries, broken bones and all kinds of crap. It's insane.

Got to pay the piper.
Yeah. It sucks too because when you get older it takes longer to heal. I can't even afford to get an MRI if I need to either. It's just the wrong timing for that crap.

Maybe in a few years when we get universal healthcare like everyone else.
Let's hope so. It could get worse from here on out too.

Yeah. Just law of the jungle, Mad Max style.
As cool as that sounded when we were kids I'm pretty sure that it isn't that cool to live in real life.

You've been pro since 2002. So 15 years deep. Do you feel like a vet? How many years is that in dog years? Dogtown years?
Well, dog years are what, like seven years to each human year? Being pro for five years feels like fifteen years so maybe its three pro years to every normal human year?

So you've been pro for 45 years?
[Laughs] Yeah. That sounds about right. Which is rad for Jason Jessee, Steve Caballero, Lance, Grosso and guys like that. Their pro years to human years ratio must be in the hundreds. Salba too. He's been around forever.

If your next step was to write a memoir of life on the road—give me five golden road rules to professional skateboard touring?
I can try. Let's see, one of them would be—and I'm a total complainer too—try to limit your complaining as much as possible. That would be rule number 1. Fly under the radar as much as possible. You probably don't want people to remember you for your complaining. You would rather they remember you for your skating. 2. Let your skateboarding talk for you.

I remember hearing about this one that seemed super obvious but for some reason this person failed to grasp it—don't use another person's towel.
[Laughs]. I guess some of them are just common sense things. These are usually dudes who don't know how to do their own laundry or cook for themselves. Those types might just grab someone else's towel getting out of the shower.

Right, because at home mom does the laundry.
Yeah. It's just common sense. Maybe that should be one of the rules. 3. Use common sense. But I guess if you don't have any that's going to be hard no matter what. Sometimes you do run into weird things on trips where dudes will actually swipe some of your shit. And you never know who does it. But I guess "Don't steal" might be a good one for some of the less bright people out there.

Feeble Jam. San Jose, CA. (click to enlarge)

Without naming names, what are the most flagrant fouls you have seen happen?
Probably the snaking stuff. On airplanes specifically though, there is one person I have flown with repeatedly who speaks really, really loud on the plane. He would basically make it to where we would get cut off from drinking on the plane. Getting other people cut off from drinks on the plane is a big no-no in my book. Keep it mellow.

Let's recap: 1) Don't complain. 2) Let your skating do the talking. 3) Learn common sense. 4) Don't steal. 5) Don't get people cut off from booze on the plane. Sounds like we got it covered.
[Laughs]. Yeah. That's the pro skater traveler starter pack.

Favorite My Little Pony?
Man, you know what? I didn't even get a board in that series. I'll stay out of it. It's cool though; they have to spread the wealth that way.

You got robbed. I have a five-year-old daughter so I know them all. Twilight Sparkle, Rainbow Dash, Applejack, Pinky Pie… the whole crew.
[Laughs]. Yeah, you're probably right in the target demographic for that series. There's probably a wide demographic of parents who will buy that for their kids.

Best memory from Toy Machine days?
There were really good times. It was never like I was bummed out on it, except when I left. I'd say every trip. But this one '02 US trip we did was like a month long—we drove across the country. Ed [Templeton] has this like sword of a dildo. It has, like, a sword handle with a hand guard attached to a dildo. It was really weird. That was like the beating stick if anybody got out of line [Laughs]. Like you would get smacked with the big dildo if nobody was feeling your music choice or whatever in the van.

Best memory from the Powell days?
Well, the team manager at the time, Rob Washburn, he was pretty awesome. He would throw out a lot of cash for specific tricks. Or maybe the first Tampa I ever entered. That was rad. Powell traveled a shit ton.

Do you consider yourself a Bones Brigade member? Technically you were, right?
I did go to Japan and I think it was marketed exclusively as a Bones Brigade trip [Laughs]. It was when Danny Wainwright and Javier Sarmiento were on too.

50-50. San Jose, CA. (click to enlarge)

Best memory from the Renaissance days?
[Laughs] I knew it was coming. Honestly, most of us got on before any of the 411 commercials came out or anything. I think when we saw those, and it became obvious what they were trying to do with the whole Christian side, that was shocking to almost everybody on the team. To us it was just free boards. They came to San Jose and told us like, "We'll give you four boards a month." Who wouldn't be stoked as a kid? I don't think any of us knew it was that type of company. They didn't really tell us. The best memory would probably be from being on a trip somewhere in the US, probably New Mexico or somewhere, but we would stay at like friends of theirs' houses. But we would sneak off and go smoke cigarettes and drink beer in the woods. That actually felt pretty good considering it was this Christian company.

Was riding for Renaissance like a Catholic schoolgirl's scenario, where it made you have to rebel for the rest of your life?
Right, like schoolgirls that go to the complete opposite end of the spectrum—just whore it up and start doing drugs [Laughs]. I think I was still too young by the time all that shit went under. I was still just a kid. But maybe it did plant the seed of rebellion.

Skating seems even more fractured into various sub-groups than usual at the moment. You have the big shoe sponsor Street League guys, the Supreme/FA army, the emerging one-rail, shaped-board, body-varial crowd, the Auby Taylor/Jeff Phillips renditions, the legacy dudes like Hosoi, Grosso, Alva, Dressen, etc… then all the Instagram heroes. Is anything stoking you out? What is your take on it all?
It's hard for me to wrap my head around because even the ones that are trying to rebel against this or that are still categorizing themselves. They're trying so hard to be creative and not categorized that it becomes it's own category [Laughs]. You're doing it to yourselves.

In the past, these transitory stages in skating have usually led to one of the groups sort of winning out and becoming the main norm of skateboarding. Which version of 2017 skateboarding do you wager will become the main deal?
Well, I always root for the underdog no matter what. At this point I'm not even sure who the underdog is. For right now, it seems like the money is going to win out. Whoever has got the money can kind of keep it going. But then again, in the early '90s at one point everybody just wore white t-shirts and blue jeans. And that sort of launched Girl and a lot of the companies that have set the tone since then. Then FA and Supreme now seem like the response to that to a degree. But honestly, at this point I don't even know what comes next.

Its funny too because classic vert now seems like the new shit too.
Dude, inverts alone are no joke. I've tried frontside inverts and they are so hard. I can do the classic invert and that's about it. I've done a few Andrechts, those are a little bit harder. But Jesus, all that stuff is hard. But as far as predicting where it goes, the Olympics will surely have some impact, if only by creating a massive backlash. I don't know who wins this war. I do know that I hope to stay out of it—that's all I know.

Is the rattail coming in hot for 2018?
God yes. Always. That would be so hard to grow for me right now though. I'm always looking for ways to save money so I got my haircut at this school for barbers. It only cost me five dollars, actually I gave him ten, but it's definitely a little shorter than I would have liked. My mom, who was always down for the rattail said this is the worst haircut I have ever had. If you want to know the next hot thing, one good way to know might be to do the exact opposite of whatever I'm doing. Because I'll probably be the guy oblivious to it all and blowing it.

On the forefront of not being on the forefront.
[Laughs]. I'm definitely not on the forefront. But I'm happy. Just happy to be alive.

Check out Caswell’s new TWS-exclusive video part: