Forerunners to the skateboard date back to the early 1900s, when European and American preteens made scooters by attaching metal rollerskate wheels to wooden planks and vegetable crates. Skateboarding as it exists today, however, was developed and popularized by surfers in the late '50s and early 1960s. Roller Derby introduced the first commercially-made skateboard in 1959: it measured 24" x 4", had clay-composition wheels spinning on ball-bearings, and sold for just under $10.00. As surfing's popularity grew in the early '60s, so too did "sidewalk surfing," with Makaha Skateboards and Hobie Skateboards emerging as industry leaders by '64, and 50 million skateboards total sold in American by mid-decade. Skaters often rode barefoot, and performed surfing-inspired tricks (back-arch turns, cross-stepping, noseriding, spinners, head-dips and coffins), along with pinwheeling 360-degree spin-turns.

The first skateboard contest was held in Hermosa Beach, California, in 1963, and attracted about 100 entrants; the '65 International Skateboard Championships, held in Anaheim, were featured on ABC's Wide World of Sports. Meanwhile, Jan and Dean's bouncy single "Sidewalk Surfing" peaked at #25 on the Billboard charts, while the Quarterly Skateboarder magazine was founded in '65, the same year "Skater Dater" was nominated for a "best live action short" Academy Award. A '65 Life magazine cover story called the skateboard "the most exhilarating and dangerous joy-ride device this side of the hot rod." On the other hand, the American Medical Association that year called the sport "a new medical menace." The injury rate was indeed sky-high, parents quit buying boards for their kids, and the sport slumped badly in the late '60s and early '70s.

With the introduction of smooth-riding urethane wheels, followed shortly by encased precision bearings, skateboarding's popularity was once again soaring by 1975. A year later, in Florida, America's first skateboard park opened; three years after that there were an estimated 300 parks across the country. Homemade plywood ramps were also popular, as were empty swimming pools, and any other type of wave-like asphalt or concrete embankment; skaters were soon getting vertical on the upper regions of ramps and pools, and by the late '70s were launching and completing aerial moves. Where a few years earlier skaters took style cues from top surfers, particularly Hawaiian ace Larry Bertlemann, now surfers began to copy skaters in an effort to bring aerials to the water. Meanwhile, Jay Adams and Tony Alva, two working class surfer-skaters from Santa Monica, California—better known to skate fans as "Dogtown"—helped give the sport a rowdy new outlaw image. (The documentary Dogtown and Z-Boys, narrated by actor Sean Penn, won the Audience Award and the Director's Award at the 2001 Sundance Film Festival.)

Skateboarding took to the streets in the early '80s, in part because skyrocketing insurance premiums had shut down the vast majority of skateparks. Pools and plywood "halfpipes" remained popular. Three skateboard manufacturers—Powell-Peralta, Vision-Sims, and Santa Cruz—dominated the industry, each promoting a team of high-profile riders, some of whom earned as much as $10,000 a month on royalties and contest winnings; the '81-founded Thrasher magazine celebrated the sport's renegade image. Fourteen-year-old Tony Hawk of San Diego, California, won his first pro contest in '82, and over the next two decades won roughly 75% of the contests he entered. Skating's influence on surfing continued, as San Clemente's Christian Fletcher, among others, borrowed freely from the skate world in order to advance the aerial form in surfing.

Following an early-'90s downturn, skateboarding's popularity again shot forward when the sport became a main attraction in the X-Games, ESPN's teen-marketed answer to the Olympics. Skate-style shoes were by that time accounting for an ever-growing portion of the youth market footwear sales; skateparks were built by the hundreds; the '99-launched Tony Hawk's Pro Skater video game series reached over a $1 billion in sales by the end of the '00s.

Today's basic skateboard is symmetrical, roughly 32 inches long, eight inches wide, concave and up-turned at both ends, and made of seven-ply sugar maple topped with traction-providing grip tape. Adjustable metal trucks are located about six inches from either end; each urethane wheel has a pair of encased bearings. A ready-to-ride ("complete") department store-bought board can cost as little as $50. A high-end custom costs up to $200. Longboards (or "cruisers") are flexible, about half-again longer than a standard board, more expensive, and are used for a smooth, stately, old-school street ride.

Skateboarding is generally divided into street-skating and vert-skating; both incorporate a constantly evolving array of tail-, nose-, and rail-slides, truck "grinds," and aerial maneuvers, executed on any variety of specially designed ramps (half-pipes, quarter-pipes, or launch ramps) or street obstacles (curbs, handrails, or benches). Specialized forms of skateboarding have also developed: downhill "street-luge" skaters reach speeds up to 90 mph; "dirt-boarders," using oversized rubber-wheeled boards, take the sport off-road. By 2012, there were an estimated 12.5 million skateboarders in America, and an enormous worldwide network of skateboarding organizations, industries, and media outlets. The International Skateboard Federation was formed in 2004, and there was talk from Olympic officials in years to come about adding skateboarding to the 2012 Summer Games, but nothing resulted—much to the relief of a goodly portion of skaters themselves, many of whom believe the sport is better served by watering its outlaw roots and steering clear of any organizational efforts.

Skateboard movies include Skateboard Madness (1980), Thrashin' (1986), Gleaming the Cube (1989), Grind (2003), and Lords of Dogtown (2005). In 2009, the Skateboarding Hall of Fame was opened in Simi Valley, California. Thrasher magazine has been publishing continuously since 1981; TransWorld Skateboarding has been published continuously since 1983.