Five Coolest Things: Freestyle is a short documentary film that provides a glimpse into the world of motocross and motorcycle racing. This documentary is part of a series that caters to motorcycle enthusiasts of all types. The host, Matt LeBlanc, is featured spending time with Travis Pastrana. At the time of the movie's release (2003), Pastrana was the undefeated freestyle champion and held gold medals in numerous racing sports. LeBlanc and Pastrana converse about a variety of motocross topics, including the popularity of Supercross racing. The relaxed interview includes Pastrana's crossover as the popular star of X-Games and rally racing, as well as video games. He demonstrates some of his more unique and dangerous moves on the motorcycle. Pastrana shows LeBlanc how to create the crowd-pleasing jumps that make the sport popular, and LeBlanc demonstrates his own non-professional skills. This installment also explores the behind-the-scenes lifestyle and passions of motorsports competitors.