esse James Hollywood was born in Los Angeles, California on January 28, 1980. His father, Jack Hollywood, was a struggling businessman.
Hollywood grew up in the area known as the “West Hills” and was on the high school baseball team. His close friends William Skidmore, Jesse Rugge, and Ryan Hoyt were also on the team. Hollywood was a skilled player but due to an injury, had to resign from the baseball team. In 1998, Jesse began selling large amounts of marijuana supplied to him by his father. One of his main buyers was 20-year-old Ben Markowtiz, who also played on the baseball team and workout out at the same Malibu gym and Hollywood.
Ben Markowitz was the older half-brother of Nicholas Markowitz (Nick). Ben and Nick came from an upper-middle class family. In 1999, Ben started buying one to two pounds of marijuana from Hollywood each week. Besides having a business relationship, the two were also friends and did cocaine and marijuana together.