Jeffrey Ross stopped by, leading Howard to ask if roasting was Jeff's one true talent. Jeff said roasting seemed to be his comedy "lane," and Howard went over some of Jeff's greatest lines. After hearing that Jackie "The Joke Man" Martling was in Sundance, Jeff joked that Jackie was there to promote his new movie, "Broke Hack Mountain." Howard asked Jeff if he'd ever turned down a roast, and Jeff picked the Mike Tyson roast, as he didn't think rapists were funny.
Jeff told the crew about his first roast, where the guest of honor, Steven Seagal, got pissed when Jeff called him a "shitty actor." Jeff also noted that a lot people thought he went too far at the Pam Anderson roast (where all proceeds went to PETA) by walking out in a full-length fur coat. Howard asked if Jeff had even been told not to joke about something, so Jeff cited the Jerry Lewis roast, when "Jerry's kids" were off-limits.
Jeff revealed that he was asked to take part in the Artie roast, but he refused after discovering that it wasn't for charity. Howard asked to hear some of the jokes he had planned for Artie anyway, so Jeff rattled them off. Jeff also told the crew that he ran into Robin on a recent flight, and he got the impression that he could've had sex with her. Howard wondered if Jeff was ready to settle down with someone like Robin, but Jeff confessed that he has a hard time staying in long-term relationships.