| Sean Penn | Narrator |
| Tony Alva | Himself (Zephyr skate team) |
| 'Baby' Paul Cullen | Himself (Zephyr skate team) |
| Jeff Ament | Himself |
| Skip Engblom | Himself (Zephyr co-founder) |
| Tony Friedkin | Himself |
| Glen E. Friedman | Himself |
| Marty Grimes | Himself (Dogtown skater) |
| David Hackett | Himself (70's skateboard champion) |
| Tony Hawk | Himself |
| Jeff Ho | Himself (Zephyr co-founder) |
| Wes Humpston | Himself (Dogtown skater/artist) |
| Jay Adams | Himself (Zephyr skate team) |
| Shogo Kubo | Himself (Zephyr skate team) |
| Joe Leahy | 50s Voice Announcer |
| Ronnie Jay Leipold | Himself (Zephyr surf team) |
| Ian MacKaye | Himself |
| Jim Muir | Himself (Zephyr skate team) |
| Steve Olson | Himself |
| Stacy Peralta | Himself (Zephyr skate team) |
| Jake Phelps | Himself (editor, Thrasher magazine) |
| Nathan Pratt | Himself (Zephyr skate team) |
| Mark Reiter | Himself (70's New York skater) |
| Fran Richards | Himself (Transworld skateboarding magazine) |
| Henry Rollins | Himself |
| Wentzle Ruml | Himself (Zephyr skate team) |
| Allen Sarlo | Himself (Zephyr skate team) |
| Bob Biniak | Himself (Zephyr skate team) |
| Tom Sims | Himself (70's skateboard champion) |
| Craig Stecyk | Himself (Zephyr co-founder; writer/photographer) |
| Steve Caballero | Himself (skateboard champion) |
| Paul Constantineau | Himself (Zephyr skate team) |
| Peggy Oki | Herself (Zephyr skate team) |
