When future generations huddle round sputtering campfires to grill their elders about what diabolical monstrosity brought the male of the species to the brink, the figure they scrawl in the dirt won't be of a mushroom cloud or a T-800 Terminator but of the metallic, top-of-the-line A5 Lux Razor kick scooter.

The Razor used to be the kind of thing Little Timmy Flyover would squeal about on Christmas morning. And then in 2008 the A5 came out with the ability to support up to 220 pounds. That's either one fat-ass 7-year-old or one ass of an adult. Sure enough, kick scooters are now a growth industry for the breed of urban commuter who lacks self-awareness, the kind of ride mid-level tech execs might use to swoosh around their ergonomic offices while hive-minding about Ellen Page's pixelated bosom in Beyond: Two Souls. Or that graying, faux-hawked fashionistas might use to zip through Nolita, despite the fact that their last attempt at trendy transit—Rollerblading—was equally egregious.

Rule of thumb: If you can park it in your cubicle or fold it into your man-purse, it is not something you want to be seen riding.

And yet alternative transportation modes like Razors, longboards, and folding bikes have become a smug, sanitized way for the North American yuppie to feign youthful rebellion as he heads to Starbucks for a 14-syllable drink.

"You're trying to say you're someone who doesn't take himself too seriously," says Emmi Sorokin of It's a Man's World image consulting, which has been making over Boston's captains of industry since 2007. "But it's easy to mistake being cool in your head with people on the street thinking, Who is this guy? It's definitely not the way you want to roll up to an investor's pitch meeting."

From Silver Lake to Greenpoint, onetime indie kids still wriggling into their Misfits T-shirts now infest bourgeois enclaves with bloated, lazily swooping longboards: three and a half feet of maple and misanthropy that take the feral subculture of skateboarding—the blood, the police chases, the sexy boys pulverizing their sexy bones—and rip out its canines. And any metropolitan hub worthy of mass transit is no doubt familiar with the pestilence of folding bikes. But paying $1,500 for something that has all the design charm of a Karen Carpenter Transformer doesn't make you hip or even eco-friendly; it just makes you look like a hipster a-hole who likes to shop the SkyMall catalog after a few too many Canadian Clubs from the beverage cart.

No matter how much they long to prove otherwise, commuters going the alt route have about as much edge as alt-rock. It's like slapping a Ducati decal on Grandpa's Rascal mobility scooter and expecting Emily Ratajkowski to hop on the back.

Paul (not his real name), an architect in New York City, was 32 when he got his first longboard. He'd skateboarded as a kid but had since graduated to more age-appropriate pursuits like running marathons. Yet somehow the allure of the longboard was too much: "It seemed like a fun way to scoot around, get coffee, meet friends." A month later he was piled in a heap clutching a wet noodle that used to be his ankle. He would need nine screws and a plate to repair an eight-inch spiral fracture. "I ate shit," admits Paul, now 36, "and I've never gotten on a longboard since."

Getting older is a gross study in diminishing returns. Your back aches, your dick needs pep pills, and the things that once made you feel alive—loud music, drugs, sex, skateboards—are eroded and codified before being handed to the next generation. And then you die. Our fathers combated this existential darkness by banging waitresses and napalming their livers. Or refinancing the house for a fire-engine-red Camaro.

For some reason, though, some men need to trick themselves into thinking they're still relevant. They pretend that the cute barista in the Death Cab for Cutie T-shirt actually knows who that is because Hey, I totally saw them at Maxwell's in 1998. But Maxwell's is closed now, and that tee is prefab from Urban Outfitters, so they make one last, desperate grab for relevance.


SKATING ON THIN ICE: Silly grown-up—these kicks are for kids.

Take it from a 23-year-old skateboarder—a real one—and just don't. "You see these guys throwing on their helmets and hopping on a scooter and you're just like, What a douche!" says Steve Goemaat, who writes about skating for the underground magazine SLUG. "You're 35, 40 years old, man. You just can't be doing that."

And yet Scooter Nation keeps cruising along. Xootr has rolled out a line aimed specifically at the junior partner who hasn't gotten rid of his Che Guevara poster. "We were originally targeting college kids," says Brian McCoy, Xootr's operations manager, "but things really blossomed when the commuters took hold." Last year, 32 percent of Xootr's sales were in New York City. The fastest-growing market? New Jersey.

But if knowing that your ride shares the same lineage on the cultural shit pile as BeDazzled sweatpants and Snooki—or that actual skaters laugh at you—isn't enough to dissuade you, do this: Google "Matthew McConaughey" and "longboard." There you will see images of an hombre at the very peak of mankind's evolutionary bell curve being reduced to a monkey shoving a twig up his urethra as he glides bro-tastically through the streets of Malibu. He even uses a wheeled stick for balance. It's called land paddling, and it is an actual thing that exists.

If a cornpone Adonis with a trophy wife and a career's worth of don't-give-a-fuck catchphrases can't pull off the longboard, what possible hope do you have?

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