The Friars Club's first televised event was the roast of Drew Carey that was broadcast on Comedy Central in 1998. Ross credits a particular joke that he made at the expense of attendees Bea Arthur and Sandra Bernhardt at the 1999 roast of Jerry Stiller for taking his roasting career to the next level. That same year Jimmy Kimmel hired Ross as a writer on "The Man Show" and Ross also wrote some of the punchlines for Billy Crystal's monologue at the Oscars in 2000. In 2003 Comedy Central began producing their own celebrity roasts. Ross has been a roaster at all Comedy Central roasts since the 2005 roast of Pamela Anderson. During his "Comedy Central Roast" appearances Ross became known for dressing-up in edgy and sometimes controversial costumes: He roasted Charlie Sheen dressed as Muammar Gaddafi; he roasted Rob Lowe dressed as "Purple Rain"-era Prince on an episode that aired five months after the musician's death; he roasted Roseanne Barr dressed as the late football coach Joe Paterno during the height of the Penn State child sex abuse scandal; he also roasted James Franco wearing cornrows and a neck tattoo in reference to Franco's character in the 2012 film "Spring Breakers". Ross has participated as a roaster on the following Comedy Central Roasts:    Ross has also written for, performed in and/or produced the roasts of the following celebrities:  Ross has taken part in several USO tours and has performed stand-up comedy at US Military bases in Afghanistan, Guantanamo Bay and Iraq. Ross first traveled to Iraq in 2003 as part of a comedy tour hosted by Drew Carey. In 2005 Ross released the film "", which he both produced and directed and which documented his experiences on the Iraq tour. That same year the film won the prize for Best Film at the Comedia film festival, a comedy film festival held annually in Montreal as part of the Just for Laughs comedy festival. In 2006 the film was shown on Showtime and also screened at that year's South by Southwest Film Festival. In 2017 the USO made Ross the Ambassador of Veterans Outreach for the Artists & Athletes Alliance. Ross published his first book, "I Only Roast the Ones I Love: Busting Balls Without Burning Bridges", in 2009. The book recounts his journey to becoming Roastmaster General and includes tips on writing roast jokes and how to put on a roast. Ross was the creator and host of the comedy panel show "The Burn with Jeff Ross", which aired on Comedy Central for two seasons from 2012 to 2013.