[10][14] His father owned and ran Clinton Manor Catering, a business that was started by Ross's great-grandmother.

[15] Ross attended Boston University as a broadcasting and film major with a minor in political science.

[19] That same year he was invited by the New York Friars Club to participate in a roast of actor Steven Seagal.

[21][22] The Friars Club's first televised event was the roast of Drew Carey that was broadcast on Comedy Central in 1998.

[30] In 2015, Ross starred in the Comedy Central 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.

[31][32] The following year he released Jeff Ross Roasts Cops where he performed for members of the Boston Police Department.

[31] The show consists of comedians competing in one-on-one roast battles where the winners are decided by Ross and a panel of guest judges.

[31][32] Ross also appeared as a battler in final episode of the show's third season in a battle with NBA player Blake Griffin.

[33] In 2018 Ross and fellow comedian Dave Attell embarked on their Bumping Mics comedy tour.

[34] Footage of their tour was also released in a three-part special, Bumping Mics with Jeff Ross & Dave Attell, on Netflix,[35] the series was filmed during three of their performances at the Comedy Cellar in New York City.

[35] Their shows consisted of observational and political humor interspersed with Ross and Attell roasting one another as well as members of the audience.

[36][37] The comedians also invited audience members onto the stage, some of whom included Bob Saget, Gilbert Gottfried, Michael Che, Amy Schumer, Nikki Glaser and Paul Rudd.

[8][40] Ross's television acting work includes roles on HBO's Six Feet Under and Crashing, and Showtime's Weeds.

[49][50] In November 2020, Ross filed a defamation suit in the New York State Supreme Court, in which multiple named witnesses (including Radtke's father) refuted her allegations; Radtke was accused of extorting Ross for "significant sums of money".