Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California showcasing his uncanny ability to persuade girls to perform sexual acts in front of his camera. As soon as Robby D saw a few video clips of real girls so thirsty for fame, they'd do anything, he immediately began working with Jack to format these video documentaries for public consumption.
| Actor | Role |
|---|---|
 Diana DollNot listed | Not listed |
 Monica SweetheartNot listed | Not listed |
| TTylar JacobsNonsex | Nonsex |
 Bobbi EdenNot listed | Not listed |
 Monica MendezNot listed | Not listed |
 Jessica JaymesNot listed | Not listed |
| Monica MendezNonsex | Nonsex |
 Alicia RhodesNot listed | Not listed |
 Jesse JaneNonsex | Nonsex |
 Barrett BladeNot listed | Not listed |
 Tyce BuneNot listed | Not listed |
 Eric MastersonNot listed | Not listed |