Inspired by the passing of U.S.O. perennial Bob Hope, Friars Club roast-master Jeffrey Ross takes Drew up on an invitation to join the U.S.O. in their ongoing mission - delivering punch-lines on the front lines. Having just bought a new camcorder, he travels to Iraq and captures his rare, intimate, and often times hilarious experience on camera. Armed with nothing but that camcorder and some jokes, Ross shoots his own life-changing experience as he travels alongside six other well known comics, entertaining battle weary G.I.'s stationed in some of the most remote parts of the Sunni Triangle.

Jeff Ross visits several cities across the country, roasting the towns and the residents in volunteer-only speed roasts. Roasting his way through cities including Seattle, Toronto, Las Vegas, Miami and Madison, Ross roasts a statue of Abe Lincoln in Washington D.C., gets roasted by John Rich in Nashville, and in Minneapolis, brings an old friend onstage to tell a very intimate story the way only Jeff Ross can.

Roastmaster General Jeff Ross talks to Black Lives Matter activists, goes on an eye-opening police ride-along, and roasts members of the Boston Police Department.

Jeff gives the most dangerous – and enlightening – roast of his life from behind the walls of the Brazos County Jail in Bryan, Texas. In this special he touches on topics surrounding incarceration such as race, solitary confinement and the death penalty.

Roastmaster Jeff Ross explores the world surrounding the U.S.-Mexico border, speaking to immigrants, DREAMers, detainees, border patrolers, human traffickers and Trump supporters. Then he puts on a show next to the border wall to roast American immigration policies, random audience volunteers and every ethnicity imaginable.