Best Jack’s Playground Collection Watch Order & Timeline (2026 Updated)

Jack’s Playground

Released: 2003 // Runtime: 105m // Rating: 6.0

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.

2003

#2

Jack’s Playground 2

Released: 2003 // Runtime: 105m // Rating: 6.0

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.

2003

#3

Jack's Playground 3

Released: 2003 // Runtime: 109m // Rating: 5.5

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.

2003

#4

Jack’s Playground 4

Released: 2003 // Runtime: 125m // Rating: 4.0

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.

2003

#5

Jack's Playground 5

Released: 2003 // Runtime: 105m // Rating: 5.2

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.

2003

#6

Jack's Playground 6

Released: 2004 // Runtime: 98m // Rating: 5.0

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.

2004

#7

Jack's Playground 7

Released: 2004 // Runtime: 99m // Rating: 5.0

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.

2004

#8

Jack's Playground 8

Released: 2004 // Runtime: 89m // Rating: 5.5

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.

2004

#9

Jack's Playground 9

Released: 2004 // Runtime: 96m // Rating: 5.0

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.

2004

#10

Jack's Playground 10

Released: 2004 // Runtime: 93m // Rating: 6.7

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.

2004

#11

Jack's Playground 11

Released: 2004 // Runtime: 83m // Rating: 5.5

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.

2004

#12

Jack's Playground 12

Released: 2004 // Runtime: 84m // Rating: 5.5

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.

2004

#13

Jack's Playground 13

Released: 2004 // Runtime: 86m // Rating: 6.5

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.

2004

#14

Jack's Playground 14

Released: 2004 // Runtime: 92m // Rating: 8.0

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.

2004

#15

Jack's Playground 15

Released: 2004 // Runtime: 89m // Rating: 6.7

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.

2004

#16

Jack's Playground 16

Released: 2004 // Runtime: 95m // Rating: 6.3

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.

2004

#17

Jack's Playground 17

Released: 2004 // Runtime: 89m // Rating: 5.0

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.

2004

#18

Jack's Playground 18

Released: 2005 // Runtime: 91m // Rating: 5.7

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.

2005

#19

Jack's Playground 19

Released: 2005 // Runtime: 88m // Rating: 5.0

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.

2005

#20

Jack's Playground 20

Released: 2005 // Runtime: 84m // Rating: 6.3

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.

2005

#21

Jack's Playground 21

Released: 2005 // Runtime: 85m // Rating: 5.5

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 .

2005

#22

Jack's Playground 22

Released: 2005 // Runtime: 88m // Rating: 6.5

Help Give A Damn - Give To The Yummypie.com Telethon

2005

#23

Jack's Playground 23

Released: 2005 // Runtime: 82m // Rating: 5.5

"Cuttin 23 Of These Ain't Easy, Damnit!" Cousin Nick P., Ph.D., drops knowledge on what it's like to cut these muthafuckas.

2005

#24

Jack's Playground 24

Released: 2005 // Runtime: 89m // Rating: 5.0

New Juicy Flavor! Longer Lasting Anal! Choc full o' fun and flavor!

2005

#25

Jack's Playground 25

Released: 2005 // Runtime: 114m // Rating: 6.0

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?

2005

#26

Jack's Playground 26

Released: 2005 // Runtime: 111m // Rating: 6.0

It's Guaranteed Analicious!! Montel's back in da house! What's da assfuckathon?

2005

#27

Jack's Playground 27

Released: 2005 // Runtime: 108m // Rating: 6.0

Analizar Esto Maricon ... Did I just speak Spanish?

2005

#28

Jack's Playground 28

Released: 2005 // Runtime: 103m // Rating: 6.0

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.

2005

#29

Jack's Playground 29

Released: 2006 // Runtime: 109m // Rating: 6.0

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.

2006

#30

Jack's Playground 30

Released: 2006 // Runtime: 100m // Rating: 6.5

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!

2006

#31

Jack's Playground 31

Released: 2006 // Runtime: 120m // Rating: 6.3

"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!

2006

#32

Jack's Playground 32

Released: 2006 // Runtime: 106m // Rating: 7.0

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'!"

2006

#33

Jack's Playground 33

Released: 2007 // Runtime: 107m // Rating: 9.0

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!"

2007

#34

Jack's Playground 34

Released: 2007 // Runtime: 0m // Rating: 6.0

Exotic waves of molten cum erupt onto timid young flesh in this amazing exploitation of carnal voracity

2007

#35

Jack's Playground 37

Released: 2007 // Runtime: 93m // Rating: 7.0

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!

2007

#36

Jack's Playground 35

Released: 2007 // Runtime: 120m // Rating: 5.5

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!

2007

#37

Jack's Playground 36

Released: 2007 // Runtime: 123m // Rating: 7.0

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!

2007

#38

Jack's Playground 38

Released: 2008 // Runtime: 122m // Rating: 7.5

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!

2008