Between 1985 and 1998, filmmaker Andy Sidaris produced series of B-movies known as the Bullets, Bombs, and Babes series. All 12 movies focused on the adventures of a team of secret agents and were mostly filmed in Hawaii. The action scenes were silly and way over-the-top and the agents were always played by Playboy Playmates (who would always get naked).
Hard Ticket To Hawaii was released in 1987 and is the second film in the series. It features a skateboarding scene. The skater was played by professional skateboarder Russ Howell. Russ, who had started skating all the way back in 1958, was actually the first professional skateboarder. He had set some Guinness World Records, one for longest handstand on a skateboard (2 minutes) and another for the most 360s (163). In Hard Ticket to Hawaii, he gets to show off both of those moves.
All 12 of these films are in a DVD collection called Girls, Guns and G-Strings: The Andy Sidaris Collection (12 Film Set)
And it's on Amazon for under $6. That's less than fifty cents a movie.
