"Funniest Comedian STEPHEN ROOT vs JEFF ROSS"

Stephen Root (born November 17, 1951) is an American film, television and voice actor. He has starred as Jimmy James on the television sitcom NewsRadio, as Milton Waddams in the film Office Space (1999), and provided the voices of Bill Dauterive and Buck Strickland on the animated series King of the Hill (1997–2010). His other roles have included Capt. K'Vada in the Star Trek: The Next Generation two-part episode "Unification" (1991), Mr. Lund in O Brother, Where Art Thou? (2000), Gordon Pibb in DodgeBall (2004), Hawthorne Abendsen in seasons 2-4 of the series The Man in the High Castle, Jim Hudson in Get Out (2017), and supporting roles in a variety of HBO series, including Boardwalk Empire, Barry, True Blood, and Perry Mason. Root began his career on stage in 1986. He made his Broadway acting debut in the play So Long on Lonely Street, where he played King Vaughnum III. He also appeared in All My Sons as Frank Lubey, and as Jon in the 2015 play Marjorie Prime. Root made his feature film debut in the 1988 film Crocodile Dundee II as a DEA Agent. That same year, he acted in the psychological horror film Monkey Shines as Dean Burbage. He had a brief cameo in the 1990 movie Ghost. Among his most recognized television roles are eccentric billionaire Jimmy James on the sitcom NewsRadio and in a recurring role on the final two seasons of The West Wing as Republican campaign consultant Bob Mayer. He appeared in many memorable comedy films, including as the mumbling, quirky Milton Waddams in Office Space; the mild-mannered gym rat Gordon Pibb in Dodgeball: A True Underdog Story; Suds, a drunk sportswriter, in Leatherheads; and the dimwitted principal in the 2008 Judd Apatow-produced comedy Drillbit Taylor. Root is a favorite of the Coen brothers. He has appeared in O Brother, Where Art Thou?, The Ladykillers, No Country For Old Men, and The Ballad of Buster Scruggs. Kevin Smith wrote a role in Jersey Girl specifically for Root.

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Jeffrey Ross Lifschultz (born September 13, 1965), is an American stand-up comedian, writer, director and actor. He is also known as the "Roastmaster General" for his insult comedy and his multiple appearances at celebrity roasts held by the New York Friars Club and on the Comedy Central Roast television series. In 2009 the Chicago Tribune called Ross "the new millennium Don Rickles." His directorial debut, the 2006 documentary Patriot Act: A Jeffrey Ross Home Movie, won the prize for Best Film at the Comedia film festival held at the Just for Laughs comedy festival in Montreal. Ross began performing stand-up in 1994 at open mic nights at the Boston Comedy Club, a now defunct comedy venue in New York City. By 1995 he was also performing at such comedy clubs as the Comedy Cellar and Stand Up NY. That same year he was invited by the New York Friars Club to participate in a roast of actor Steven Seagal. Ross became a regular at the Friars Club roasts and was given the title of "Roastmaster General". 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.

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