Cliff aka "Jamil"

Season 8

Growing up in New Jersey, Cliff watched his friends and family members go in and out of the prison system, and share horror stories of the conditions. Cliff has never been incarcerated and credits his supportive family for keeping him out of trouble and encouraging him to excel in school. Cliff has had a couple run-ins with law enforcement, and often wonders how different his life would have been had he been incarcerated. Cliff wants to better understand the challenges his loved ones face behind bars.

Cliff is confident he’ll withstand 60 days in jail. As a child, he was exposed to drugs, gang activity and violence, and his incarcerated cousins shared their experiences with Cliff on how to navigate life behind bars. Cliff also has family members who’ve worked in law enforcement and corrections, so he has an idea of how jails should and shouldn’t be run.

In October 2021, Cliff’s best friend was the victim of a homicide. Heartbroken from the senseless loss of life, Cliff is going undercover to honor his best friend and encourage young guys to use their words instead of guns. Cliff considers himself a mediator and wants to inspire his podmates by sharing his positive message of unity and hope. Today, Cliff is a proud dog-dad; he works in film and is a hip hop and rap recording artist.