The first skateboards were actually more like scooters, with the undercarriage consisting of roller skate Wheels attached to a two by four. Once the push bar of the scooter-like contraption was broken off, Skateboarding was born.

It wasn't until the 1950's, when the surfing craze was in full swing, that people realized skateboarding Could recreate the feeling of riding a wave. This connection with surfing gave skateboarding a direction that would influence everything to come, from maneuvers and style, to terrain, fashion and attitude. It was during this time that modifications were made to the trucks making it easier to maneuver. By 1959 the first Roller Derby Skateboard was for sale. 

In the early 1960's companies such as Larry Stevenson's Makaha and Hobie Alter's began to mass-produce the first true surfing-inspired skateboards. Some of the early proponents of surf-style Skateboarding included Bill and Mark Richards, Dannu Bearer, Bruce Logan and Torger Johnson. Skateboarding became very popular almost overnight, and companies were fighting to keep up with demand. Over fifty million skateboards were sold within a three year period, and the first skateboard contest was held in Hermosa Beach, CA in 1963. 

Right after skateboarding became a craze it all too soon slumped. This is when  Larry Stevenson invented the kicktail, and the first generation of skateboarders laid down the foundation of tricks and style. However, they were still largely limited by equipment. Then in 1973 the urethane wheel was invented, revolutionizing the sport. The new wheels provided much better traction and speed and, combined with new skateboard specific trucks, allowed skaters to push the difficulty of maneuvers to new levels.

During the 1970's skateboarding experienced a large growth stage whish saw the construction of numerous concrete skateparks, a rank of professional skaters, magazines and movies. During this period modern skateboarding evolved to include vertical skating among its disciplines of slalom, downhill, freestyle and long jump. Key advances in the sport included the aerial, the invert and the ollie, which may be the single most important trick in the evolution of skateboarding, next to the kick turn. This was the first time skateboarding had stars, some of the first really big names being Tony Alva, Jay Adams and Stacy Peralta. The look of skateboards also changed providing better stability on vertical surfaces. 

In the 80's the plywood ramp and streetstyle revitalized skateboarding just as the urethane wheel had revitalized the sport in the 70's. Forced to take an underground, do-it-yourself attitude, skaters began to create their own wooden skate ramps in backyards and empty lots and turn previously unrideable street terrain, such as walls an handrails, into free-skate parks. Skater-owned companies became the norm and innovations in board and truck size allowed the trick envelope to be pushed even further. With all this grass-roots action taking place it was inevitable that skateboarding would go through another growth phase.

The current cycle of skateboarding has been fueled by many items including new companies, more varied and difficult terrain, a new, more hard-core, almost dangerous attitude, and most importantly by a new generation of kids. 

Today a pro can make anywhere from $1000 to $10,000 a month. These earnings are based on winnings, depending on how well a skater places in any given competition and how many competitions a skater competes in during any given month. Most skaters who are sponsored also earn a monthly salary from one or more companies, which sponsors them as team riders.

Skateboarding can be enjoyed by kids as young as two years, but the majority of pro skaters' range from early teens to early twenties. Most skateboarders don't train in any usual sense of the word, and they don't even think about their diet. Skaters just do what they love to do: skate, all the time. Skateboarding is fun, and when having fun is the goal, it never seems like training. Of course many skateboarders do other things for fun as well, such as surfing and snowboarding, which is actually extreme sports cross-training. 

In regards to the "ten-year cycle," the sport once again started on an upward swing in 1995, due in part to exposure it received from ESPN's first Extreme Games in Rhode Island. This served to bring skateboarding, which had long been viewed as a rebel sport, perhaps a step closer to the mainstream. In 1996 the Extreme Games were again held in Rhode Island, once more exposing the sport of skateboarding to millions of people. Skateboarding was also included in the 1997 Winter X Games in the form of a CrossOver event that also included in-line skating, bicycle stunt, and snowboarding.

The impact of media coverage on skateboarding has moved it from an underground sport to a spectator sport over the last four years. It was brought an influx of companies and their advertising dollars, which had previously ignored skateboarding. Advertisers have seen that skateboarding has become a prime sport through which they can reach their favorite demographic: youth males.

Skateboarders have been present in campaigns for products from soft drinks to potato chips, candy to phone companies. But the primary focus of the sport remains on street skating, as can be seen throughout both the editorial and advertising pages of the major skateboard magazines, where street skating photos continue to dominate. However vert skating is making a comeback, due in part to the large number of new skateparks being built. Many different ramps, pipes and bowls present at these parks have led to a change in equipment. These technological changes applied to skate products have improved skateboarding hear steadily over the last two decades. While in the early 90's small boards and tiny wheel ruled, now there is a wide range of boards and wheels being seen under the feet of skateboarders. Wheel diameters are larger, deck width continues to grow, and longboards are gaining in popularity, especially in beach communities and among those that just want to use their skateboards to cruise or as a mode of transportation.

There have been many organizations and governing bodies for skateboarding throughout its history. The two main organizations today are the IASC (International Association of Skateboarding Companies), and World Cup Skateboarding, which is the leading competition organization. World Cup Skateboarding is run by former NSA (National Skateboarding Association). Competitors are usually on factory teams, rather than national teams. This is due to the growth of sponsorship and sponsorship dollars put into events.