Jack be Nimble. Jack be Quick. Jack has a video camera so suck Jack's d***k! Jack's Playground is a brand new reality series featuring 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. When Digital Playground director, 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.