Freestyle skateboarding (or freestyle), perhaps the oldest style of skateboarding, is a type of skating that was popular intermittently from the 1960s until the early 1990s, when the last large scale professional competition was held; it would be 8 years until the next (2000). The emphasis in freestyle is technical flat ground skateboarding. Often a freestyler will need little more than a board and a smooth, flat surface. Music and choreography have always been an essential part of the professional freestyle routine. Freestyle in the 1950s was a direct result of surfing (or the lack of it). Surfers would imitate their moves on skateboards when the waves weren't breaking. In the 1960s, many freestyle tricks were derived from gymnastics and dancing. In the 1970s and 1980s Freestyle progressed toward technical, fluid and more creative routines. Influential Freestylists of this era included Russ Howell, Rodney Mullen, Joe Humeres and Per Welinder. Freestyle changed significantly in the 1980s, when ollies and ollie based flip tricks were invented and introduced to the discipline.
In 1995, pro freestyler Stefan "Lillis" Åkesson started the International Network for Flatland Freestyle Skateboarding (INFFS) and (with Daniel Gesmer) produced Flatline and the online version Flatline Online. All over the world freestylers realized they were not alone and through the Internet they could connect and interact in ways never done before. In the year 2000 the World Freestyle Skateboard Association WFSA was founded by Bob Staton, Åkesson and Gesmer. Freestyle now started to attract more interest. The main skateboarding media is still focused on streetskating and vert but magazines that focus on other "alternative" skateboard disciplines, such as bowl, slalom and longboarding, have shown an interest in covering some of the activities in freestyle.
The style has been fused to an extent with street skateboarding through professional riders such as Rodney Mullen, Per Welinder, Kilian Martin and Darryl Grogan.