It's hard to think back to a time when skateboards and motorcycles didn't go hand in hand. Looking closer, it's easy to see the appeal with all the similarities the two lifestyles share: an individualistic pursuit pulled off either solo or with a crew that allows the riders' sense of style to shine through with a looming risk of injury at all times. Check. Check. Check.

Emerica's Wild Ride may be the first skate/bike combo that comes to mind, but the relationship was formed way before that, with early day renegades like Jason Jessee, America's original skateboarding/motorcycle riding renegade. Canadian's have been getting in on the action as well, with the photography of Scott Pommier, Vancouver's cruising Creepy Friendlies, and the two-wheeled nomadic ways of Keegan Sauder (you can't forget his Jessee-esque Zero ad, surfing his cruiser).

Keegan's Zero ad.

By no means a definitive guide, let's look at some of the major players and events that crossover the skate scene and grease monkey lifestyle.

Jason Jessee: American Anti-hero
Perhaps the most controversial skateboarder of all-time, Jason needs no introduction for anyone that has ever flipped through Thrasher. This gun-toting, custom bike building wild man lived larger than life and went even higher above transitions. Famously quoted as saying "I want to die -- especially on my bike." Gnarly.

Pray for Me: The Jason Jessee Movie was released in 2006 and showcased both the legendary skate and metal working skills of this American anti-hero. Want to know who your favorite pro's favorite badass is? It's Jason Jessee.

Pray For Me: The Jason Jessee Movie trailer

Vans got into the greasy side of things by designing two pro-model shoes with Jason. Both of these chopper-inspired shoes aimed to "define versatility, bridging the gap between skate functionality and the rugged demands of riding motorcycles."

The latest Sk8-hi's feature a slit in the shoe below the achilles for easier kick starts on your chopper, while the shoes from a few years ago came with a second pair of insoles that had a metal plate beneath them for added stability on the pegs.

Max Schaaf: Skateboarder/ Owner of 4Q Custom Conditioning
Bay Area skateboard legend Max Schaaf has had the support of skate brand DLX since back in the day, but after catching the chopper bug years back he now has a fall back plan involving his second love. 4Q Custom Conditioning not only builds and paints custom bikes, but also sells merchandise. You can see Canadian ruler and fellow two-wheel enthusiast Ryan Smith sporting it up top in his latest Skateboard Mag interview.

Getting into motorcycles for some of these guys can be just as addictive as when they first discovered skateboarding. Max was interviewed for streetchopperweb.com, where he described his chopper beginnings as an unknown lurking through Bay Area bike swaps, labeled the "skinny skater kid", but in a short amount of time became known as "Max with the really cool Shovelhead."

Vans once again showed their support for the chopper scene by letting Max design two Oakland-style Vans shoes that came with handle bar grips, fireproof suede, and a custom shoe box that looks like it houses vintage tools.

When he isn't cruising on his 1947 Harley Knucklehead, Max keeps his 4Q blog updated frequently so check it out. Max also has a "Day In The Life" on the Fourstar site that's worth a few minutes of your day.

Emerica's Wild Ride
Since the mid-millennium, Emerica has been sending their team out on the road Easy Rider-style in the first-ever fully interactive professional skateboarding tour. Not only does their top tier team strap their decks to their Harleys but they invite the general public to take part in their outlaw ways by joining the caravan to camp and skate with the team, wisely tagging it with a parental advisory: "As with any real professional skateboarding tour, some materials and situations may not be suitable for persons under 18 years old." Got that right.

The tour usually culminates with a bang, on June 21, Go Skateboard Day, for Emerica's Wild in the Streets. Genius. They even enlisted the help of skate media darling Patrick O'Dell to come along and document the action for his Epicly Later'd featured series on VBS.tv. Heath Kirchart might have been one of the first to get the Harley sickness but others like Spanky, Braydon Szafranski, Leo Romero, and Bryan Herman followed quickly behind. Apparently, Andrew ‘The Boss' Reynolds is quite content chilling in the van and sleeping in hotel rooms while the others rough it on two-wheels and in grimy campsites every night.

RVCA's Mild Ride
RVCA's Mild Ride was a mini-tour in which the RVCA team rode Vespa scooters from Costa Mesa to San Francisco, California, with several stops in between to skate and visit retail accounts. While very much a thinly veiled, two-wheeled, lower CC* spoof of the Emerica's popular Wild Ride, who's to say riders such as Ethan Fowler, Leo Romero and Keegan Sauder didn't have just as much fun? Ironically, the Mild Ride was also a feature episode on Epicly Later'd. Check the video to see how Vespa's become the perfect tow vehicle to get extra speed for big gaps.

Keegan Sauder: The Canadian Contingent
West Coast-based but nomad by nature, Keegan Sauder is one of Canada's best-known motorcycle fanatics. The two-wheel lifestyle is perfectly suited for Keegan to fill a backpack and take off. Whether it be down Main St. to set up a deck at Antisocial or across the Mongolian countryside on a two-month tour.

Back in ‘06 he was featured in a Zero ad surfing his cycle down the street doing his best Jason Jessee impression (standing on his seat, no hands) by fellow Canadian gearhead Scott Pommier. Keegan knows the inherent risk of such actions, though, as he says, "There are two kinds of riders, those who have gone down and those who are going to."

Keegan's garage reads like a gearhead's Christmas list:
- 1973 Honda cb350
- 1971 Triumph Tiger650
- 1978 Yamaha sr500
- 1967 Harley D. Troublehead.

The Downside: Ryan Smith's Near Fatal Motorcycle Crash
Ryan Smith has taken some pretty gnarly slams in his day, but no skate fall can compare to a bad motorcycle crash. In fall of 2007, Ryan woke up in the hospital hooked up to a catheter, a breathing tube, a feeding tube, and wearing a neck brace. With no recollection of what had happened, the doctors told him he crashed his motorcycle.

His injuries were as follows:

-       crushed right hand (reconstructed),
-       compound leg fracture (rebuilt with a titanium rod),
-       pelvis fractured in 3 spots
-       fractured skull (brain bleeding in 2 spots), 
-       caved in cheekbone (plastic surgery fixed that one)

While coming back stronger than ever (check out his interview in The Skateboard Mag for further proof), the accident kept him off his board for over 6 months and health care costs took a massive financial toll. The passion can't be stopped for these guys; he's already back on his motorcycle.

Just like skateboarding, riding a motorcycle is a perfect way to view and interact with your surroundings, whether just riding down the street or using it as a vehicle to see different countries and cultures. No doubt you will meet a variety of characters and hit some unique terrain, adding that necessary added element of risk that will make something special happen. Live to ride...ride to live. Or something like that.

All photos: Scott Pommier

* CC="cubic centimetres", referring to the size of an engine, for those who had no idea

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