His appearance during a 1996 Monday night open mic night in New York City at the now closed Greenwich Village location of the Boston Comedy Club (coordinated by Tracey Metzger) appears in the movie Celtic Pride.

Ross credits a particular joke made at the expense of Bea Arthur and Sandra Bernhardt at the Friars Club roast of Jerry Stiller in 1999 for creating his roasting career. Ross was both the show's Producer and a guest. It was not the joke itself, which he claims was not that funny, but Arthur's wordless reaction to it. He said "I felt like she [Bea Arthur] put me on the map because everywhere I went people were quoting this joke to me."

Ross' sole directing credit, Patriot Act: A Jeffrey Ross Home Movie (2005), received the Best Feature Film Award at the Montreal Comedy Festival. The documentary is about Ross' life-changing experience entertaining U.S. troops stationed around Iraq. It features fellow comedians/comic actors Drew Carey, Blake Clark and Kathy Kinney.

Ross and his sister attended Boston University; he graduated from its College of Communication. In a 2008 interview for the student-run BUTV10 program Full Circle, Ross mentioned that during his college years he was the Director at BU's WTBU and worked at the local NPR affiliate.

Ross is the author of I Only Roast the Ones I Love: Busting Balls Without Burning Bridges, a book released September 15, 2009. It recounts his rise to stardom and, includes tips on writing roast jokes and has ideas on how to put on a roast.

On August 14, 2012, Jeff Ross debuted his weekly Comedy Central show The Burn with Jeff Ross, which aired for two seasons.

In 2015, Ross starred in the Comedy Central TV special, Jeff Ross Roasts Criminals: Live from Brazos County Jail, where he performed stand-up comedy for male and female convicts in Brazos County, Texas.