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A Brief History of Skateboarders Smoking Cigarettes While Skateboarding

Looking back on a (mostly) unfortunate trend.
Dan Drehobl. Photo by Brynce Kanights

Extreme sports and unhealthy lifestyles represent polar opposites on the danger scale. In the former, any resulting harm is delivered immediately; in the latter, the damage is accumulated much more slowly, with effects lying dormant for years. The nice thing about an activity like BASE jumping is that, as soon as you decide you’re done leaping off buildings—assuming you haven’t already incurred a related injury—you’re as healthy as if you’d never done it at all. With this risk spectrum in mind, when I see a skateboarder do a trick while smoking a cigarette, I can’t help but feel inspired by the sheer audacity involved. Even if, as Etienne Gange does in the new Alltimers video, a skater manages to land a long 50-50 without burning himself or catching an ember in the eye, he could still feel repercussions decades later in the form of emphysema, heart disease, and any number of cancers. Talk about staring death in the face!


Of course, skateboarding and smoking have both been traditionally marketed as rebellious, commendably anti-social activities. Just look at all these cigarette-themed skate graphics. But in recent years things have changed. Like it or not, skateboarding is a soon-to-be Olympic sport, and the number of kids smoking is at an all-time low. So as we charge ahead into this healthier new world, let’s take a moment to reflect on the endangered fad of smoking while skating.

To be clear: Smoking is not cool. “Where is the rebellion in acting like a fuck-up?/ Why not embrace simple health?” Phil Elverum sings on Mount Eerie’s “Don’t Smoke.” Then again, that song is really the only piece of art that has ever made me not want to smoke, as opposed to thousands of photos and paintings and films showing smokers looking, well, cool. Simply: It’s glamorous when people disregard safety in the pursuit of pleasure, and no amount of medical data can change that. But then, some smokers look better than others. Kevin Rodrigues's fumeur Parisian street gap early grab–to–curb bash in Converse's new video Purple (at 10:39) works because he's a French malcontent. Tom Penny’s cigarette switch flip, from the first Transworld video, is part of a barrage of legendary tricks over the San Diego chain-to-bank. I don’t know if Brandon Biebel (who is sort of the American Tom Penny, when you really think about it) is still addicted to cigarettes, but with his flawless abs and athletic gear, a cigarette would be all out of proportion. Similarly, there’s something awkward about the skaters I like to think of as Teenage Smokers, after Ed Templeton’s photo book of the same title. Underage smoking is one of those things that really only looks charismatic when you’re even further underage; otherwise the combination of backpacks and hard packs is just discordant. Bill Strobeck’s entourage of Supreme ams can fall into this category. So does Arto Saari’s feeble five-o to fakie in Sorry. Arto’s part in that video is two Bowie songs long, encompassing both the late-puberty years and his early prime, but the cig trick is pure teen bravado. A friend has to stop him from sliding into oncoming traffic, and Arto’s head jerks in a way that almost bangs the ember into his buddy’s face—not exactly Camel smooth.


Andrew Reynolds’s part in Stay Gold is the culmination of a career, the last full showcase of one of the all-time greats. It’s nearly perfect, marred only by its overly twee indie soundtrack, and there’s no posturing when the Boss smokingly switch frontside flips a large four block near the end. He just lands and brings his right hand up to his mouth. Reynolds’s pre-trick “madness” is well documented, and one gets the sense that he was resting with a cigarette in between tries when he was struck with a burst of bravery and didn’t want to wait for the cigarette to be finished, lest the confidence (or whatever emotion allows a man to jump down a head-high set of cement, switch) dissipate. The shot does not linger on the cigarette but instead quickly advances to the next trick, a huge fakie 360. I bet that Reynolds, who transformed himself from a preeminent Piss Drunk into a genuine role model, would have cut the cigarette entirely if he could have.

The early 2000s were in many ways the pinnacle of smoking and skating. There were the Piss Drunx, Arto Saari in Sorry, and Frank Gerwer’s chain-link fence tailslide to hill bomb. Then of course there’s Enjoi’s Bag of Suck, the only skate video to ever open with a Surgeon General’s warning about the harmful effects of tobacco use. Shoelace belt–era Jerry Hsu lights a cigarette from his burning thumb, Caswell Berry looks like a stock clerk whose break isn’t long enough for him to separately suck down a stogie and varial heelflip a roof gap.


More recently is Pete Eldridge’s 2012 NYC night line. In most of these clips, the skater’s cigarette remains in hand (or, sometimes, mouth). Eldridge’s is notable for the fact that he actually brings his hand up to his mouth, inserts the cigarette, holds it in his lips for a few seconds, removes it, backside heelflips an electrical grate, and finally exhales smoke. As Quartersnacks wrote in their roundup of the Chillest Lines in Skateboard History, “He was far from the first to skate with a cigarette, but he is the closest skateboard-equivalent of some 1940s movie star smoking in black and white film, and looking undeniably awesome while doing it.”

Any smoking and skating analysis would be incomplete without mentioning Dan Drehobl, the man who turned smoking while skating from a stylistic affectation into a lifestyle. Drehobl has been ripping for decades, but the main thing skaters of a certain age know about him is that in most of his ads he had a smoke in his mouth—sometimes several. Drehobl and cigarettes were so connected that, in 2003, when professional skater and noted hater Tim O'Connor wrote a list of bad skateboard tricks, number six was “Skating with a Cigarette in Your Mouth if You’re Not Dan Drehobl”: "This is another one of them cases where people are trying to give the illusion that everything is so easy for them that they can enjoy a nice flavorful smoke while trying the trick of their life. It’s all lies kiddies!”


Drehobl agrees. In 2013, he told Muckmouth that he’d even taken up e-cigs in an effort to cut back. “I think smoking sucks and I wish I could just quit. Cigarettes are addictive as fuck and they get you by the balls and they make you feel like shit. Sure it's funny to joke around about but I'd just like to tell any kids that are reading this that if they haven't picked it up yet I would advise them to never try it.”

The good news, both for critics like O’Connor and for those concerned with the long-term health of skateboarders, is that youth smoking rates are lower than ever. The percentage of skateboarders who smoke isn’t exactly the kind of thing measured by the CDC, but if the general population is any indication, the days of smoking while skating are numbered.

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