Jack’s Playground in order

Jack’s Playground collection from Digital Playground 38 films, 61h 25m in all, in release order.

Jack’s Playground
Jack’s Playground
2003 · 105 min
Jack, a trust fund child and aspiring music video director who happens to have a knack for persuading real girls to perform sexual acts in front of his camera. Jack's personal videos are home made in Santa Monica, California.
New
Jack’s Playground 2
2003 · 105 min
Jack, a trust fund child and aspiring music video director who happens to have a knack for persuading real girls to perform sexual acts in front of his camera. Jack's personal videos are home made in Santa Monica, California.
New
Jack's Playground 3
2003 · 109 min
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.
New
Jack’s Playground 4
Jack’s Playground 4
2003 · 125 min
Jack, a trust fund child and aspiring music video director who happens to have a knack for persuading real girls to perform sexual acts in front of his camera. Jack's personal videos are home made in Santa Monica, California.
New
Jack's Playground 5
2003 · 105 min
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.
New
Jack's Playground 6
2004 · 98 min
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.
New
Jack's Playground 7
2004 · 99 min
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.
New
Jack's Playground 8
2004 · 89 min
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.
New
Jack's Playground 9
2004 · 96 min
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.
New
Jack's Playground 10
2004 · 93 min
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.
New
Jack's Playground 11
2004 · 83 min
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.
New
Jack's Playground 12
2004 · 84 min
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.
New
Jack's Playground 13
2004 · 86 min
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.
New
Jack's Playground 14
2004 · 92 min
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.
New
Jack's Playground 15
2004 · 89 min
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.
New
Jack's Playground 16
2004 · 95 min
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.
New
Jack's Playground 17
2004 · 89 min
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.
New
Jack's Playground 18
2005 · 91 min
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.
New
Jack's Playground 19
2005 · 88 min
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.
New
Jack's Playground 20
2005 · 84 min
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.
New
Jack's Playground 21
2005 · 85 min
Sorry about Jack's 20, folks. I bitchslapped Jack to make sure that won't happen again. Montel Returns and Cody Law Rights For The Ring .
New
Jack's Playground 22
2005 · 88 min
Help Give A Damn - Give To The Yummypie.com Telethon
New
Jack's Playground 23
2005 · 82 min
"Cuttin 23 Of These Ain't Easy, Damnit!" Cousin Nick P., Ph.D., drops knowledge on what it's like to cut these muthafuckas.
New
Jack's Playground 24
2005 · 89 min
New Juicy Flavor! Longer Lasting Anal! Choc full o' fun and flavor!
New
Jack's Playground 25
2005 · 114 min
Loads And Loads Of Spankin' Good Times! Watch Tera take the double Buda! See Rocki take it in the... barn... and will Tommy ever pop?
New
Jack's Playground 26
2005 · 111 min
It's Guaranteed Analicious!! Montel's back in da house! What's da assfuckathon?
New
Jack's Playground 27
2005 · 108 min
Analizar Esto Maricon ... Did I just speak Spanish?
New
Jack's Playground 28
2005 · 103 min
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.
New
Jack's Playground 29
2006 · 109 min
Drop It Like Its Hot! Julia Ann's taking loads on her feet. 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.
New
Jack's Playground 30
2006 · 100 min
Jack's Playground 30 is packed full of the dirtiest chicks enjoying giving awe-inspiring blow jobs, masturbation, ball-bustin' tease, and pussy lovin' action. Featuring busty, brunette superstar Jenaveve Jolie, Jack's Playground 30 includes hotties Taryn Thomas, Jelena Jensen, Renee Richards, Rita Faltoyano, and Marlena. Jack's Playground is a collection of Jack's personal videos, homemade in Santa Monica, California. Jack uses his uncanny ability to persuade girls to get wild and kinky in front of his camera. These girls will do anything and anyone for their promised 15 minutes of fame! Welcome to Jack's world!
New
Jack's Playground 31
2006 · 120 min
"Jack's Playground 31," the superstar edition, stars the lovely Jana Cova in two delectable scenes, Devon in all her naked splendor and DP's original contract star, Rocki Roads in brand new, never-before-seen footage. She lets Vince Vouyer spin her around and pleasure her all over. Jasmine Byrne does a phenomenal, chart-topping anal scene with Scott Nails, who also has the pleasure of some fun pussy play with Bianca Pureheart. Add the gorgeous Taryn Thomas and exotic Isabella to the cast, and "Jack's Playground 31" is a sure-fire, all-holes-filled, cum-fest. Intertwined throughout the stroke material, is plenty of entertaining "Jack's TV" featuring Montel and Cody!
New
Jack's Playground 32
2006 · 106 min
Jack's Playground 32 Adult DVD Description: "Jack's Playground 32, features Digital Playground's contract babe, Sophia Santi, eager to make it in the music video scene. She shows her distinct talent and raw, exquisite beauty in two delectable scenes. Then Michelle Maylene proves she will do anything for fame too. Flower Tucci goes with the “wetter is better when you are doing anal” mantra and Alexis Silver pushes her pretty titties into the sex fest. Jelena Jensen is back again, proving her dedication and Brooke Haven makes herself a prime candidate by throwing some heavy anal action into the mix. Jack's Playground 32 is a sure-fire, all-holes-filled, cum-fest. Intertwined throughout the stroke material, is plenty of entertaining 'Jack's TV'!"
New
Jack's Playground 33
2007 · 107 min
Jack's Playground 33, features Digital Playground's one and only insatiable and sexy Devon. She's eager to make the music video cut and demonstrates her distinct talents on Scott Nails' throbbing cock. She has mastered the corkscrew and just about every other blowjob technique ever invented; Scott gives her his vote as he fucks her beautiful face. Jerry, on the other hand, is pushing for Devaun and Renee Richards, who get together and tag team him in a delectable sex-travaganza. Tantalizing Bree and sensual Celeste Star don't want to share the camera. They let everyone get off watching them get off. Sara Stone delivers a dynamic tryst with a sloppy wet titty fuck, more than proving her worth. Before 33 wraps, Riley Mason makes herself a prime candidate by throwing some heavy lovin' into the mix. Jack's Playground 33 is a sure-fire, sensational, cum-fest. Intertwined throughout the stroke material, is plenty of entertaining "Jack's TV!"
New
Jack's Playground 34
2007
Exotic waves of molten cum erupt onto timid young flesh in this amazing exploitation of carnal voracity
New
Jack's Playground 37
2007 · 93 min
Jack is really busy casting for music videos and now he's landed Digital Playground's super fine contract star, Jesse Jane®. She fucks Ben English every which way in true gonzo style. Throughout Jack's Playground 37, you will enjoy similar sexcapades with Kelsey, Roxy, Jelena, Sue & Valentina We don't know what band is going to use the footage on MTV but we guarantee that all the bands are going to use the footage for something! True to Jack's good sense, there's a lot of tease and a lot of action and it's all entertaining! Forget professional" this volume is all about totally fuck-able chicks and lube. Go at it!
New
Jack's Playground 35
2007 · 120 min
Jack is really busy casting for music videos and now he's landed Digital Playground's super fine contract star, Teagan Presley. She takes a big cock in the butt and we KNOW Scott Nails found some SWEET ASS pleasure deep in her crack. We don't know what band is going to use the footage on MTV but we guarantee that all the bands are going to use the footage for something! True to Jack's good sense, there's a lot of tease and a lot of action and it's all entertaining! Forget professional this volume is all about totally fuck-able chicks and lube. Go at it!
New
Jack's Playground 36
2007 · 123 min
Jack is really busy casting for music videos and now he's landed Digital Playground's super fine contract star, Sophia Santi alongside Selina Draagen, Alyssa Chase, Carli Banks, Marlena, Christina Brooks and Holly Wellin. We don't know what band is going to use the footage on MTV but we guarantee that all the bands are going to use the footage for something! True to Jack's good sense, there's a lot of tease and a lot of action and it's all entertaining! Forget professional... this volume is all about totally fuckable chicks and lube. Go at it! Let The Unwrapping Begin!
New
Jack's Playground 38
2008 · 122 min
Jack is really busy casting for music videos and he's scored some super fine ass for volume 38. Digital Playground's amazing contract super stars Teagan Presley and Lacie Heart join an all-star cast that includes blowjob maven Audrey Bitoni plus Leah Luv, Neveah & Roxy Deville. This is gonzo fucking and sucking at its primal and animalistic best. Throughout Jack's Playground 38, you will enjoy horny and engagingly delicious scenes. We don't know what band is going to use the footage on MTV but we guarantee that all the bands are going to use the footage for something! True to Jack's good sense, there's a lot of tease and a lot of action and it's all enter-taining! Forget professional... this volume is all about totally fuck-able chicks and lube. Go at it!
New

Frequently asked questions

What order should I watch Jack’s Playground in?

1. Jack’s Playground (2003), 2. Jack’s Playground 2 (2003), 3. Jack's Playground 3 (2003), 4. Jack’s Playground 4 (2003), 5. Jack's Playground 5 (2003), 6. Jack's Playground 6 (2004), 7. Jack's Playground 7 (2004), 8. Jack's Playground 8 (2004), 9. Jack's Playground 9 (2004), 10. Jack's Playground 10 (2004), 11. Jack's Playground 11 (2004), 12. Jack's Playground 12 (2004), 13. Jack's Playground 13 (2004), 14. Jack's Playground 14 (2004), 15. Jack's Playground 15 (2004), 16. Jack's Playground 16 (2004), 17. Jack's Playground 17 (2004), 18. Jack's Playground 18 (2005), 19. Jack's Playground 19 (2005), 20. Jack's Playground 20 (2005), 21. Jack's Playground 21 (2005), 22. Jack's Playground 22 (2005), 23. Jack's Playground 23 (2005), 24. Jack's Playground 24 (2005), 25. Jack's Playground 25 (2005), 26. Jack's Playground 26 (2005), 27. Jack's Playground 27 (2005), 28. Jack's Playground 28 (2005), 29. Jack's Playground 29 (2006), 30. Jack's Playground 30 (2006), 31. Jack's Playground 31 (2006), 32. Jack's Playground 32 (2006), 33. Jack's Playground 33 (2007), 34. Jack's Playground 34 (2007), 35. Jack's Playground 37 (2007), 36. Jack's Playground 35 (2007), 37. Jack's Playground 36 (2007), 38. Jack's Playground 38 (2008).

How long does it take to watch all of Jack’s Playground?

About 61h 25m across 38 released films.

Do any Jack’s Playground films have post-credit scenes?

None are listed on TMDB.