Jeff Ross, 25 Years of Roasts

Jeff Ross comes on to promote his Broadway-to-Netflix special Take a Banana for the Ride, and the conversation pulls in 25 years of friendship with Rich, the healing power of roasts, and one of the best Don Rickles stories ever told on this show.

Ross had seven inches of his colon removed. Now he has a semicolon. That's the joke, and it's also where the show lives. His mission statement: if we don't laugh, we cry. He opens up about his health, his family, losing his parents as a teenager, and living with his grandfather Pop Jack who used to send him off to New York open mics with a few dollars and the line that became the title. You never know. You might get low blood sugar. Take a banana for the ride.

Ross wears a ring his grandfather made from a steel bolt pulled off the U-505, the captured Nazi U-boat Pop Jack helped maintain as a shipbuilder in Baltimore during World War II. He sanded it down and wore it his whole life for what he called world beater energy.

The middle of the conversation goes back to how Rich and Ross actually met. Two weeks after 9/11 in New York. John Mosley introduced them on the street. Ross asked if Rich had a tuxedo. The Hugh Hefner roast was about to happen, and Ross had fought Comedy Central and the Friars Club to keep it on the calendar. His argument: cancelling was letting the terrorists win. They moved the afterparty money to 9/11 charities and went on with it.

Rich was five seats from the dais. Kimmel hosted. Colbert, Triumph, Carell, Cedric, Schneider, Silverman all there. Gilbert Gottfried closed. His 9/11 jokes got the room shouting too soon from the rafters, and he pivoted mid-set into The Aristocrats. Bob Saget helped tell the full version in the Paul Provenza documentary that followed.

On the Tom Brady roast, Ross lands something real. Having Belichick come out Darth Vader style, having Kraft there, Gronk spiking Kevin Hart into glass. Those guys had not been in a room together. It was icy. The roast cleared the air before Brady's Patriots Hall of Fame induction a month later, and Ross argues Brady deserves something close to a Nobel Peace Prize for agreeing to it, live and unedited, for three hours and six minutes.

The Kevin Hart roast is coming Mother's Day on Netflix. Shane Gillis hosts. Ross is pushing for The Rock.

The closer is a two-part Rickles story. The famous Sinatra beat. Then Ross's own father, Ronnie Lifschultz, New Jersey catering legend, running the same play on Rickles years later at Resorts International. My dad drops his fork and says, I'm eating, Don. Rickles slapped his knee. For years Ross wondered if it really happened. Then the daughter of his dad's girlfriend sent him a note after Broadway confirming it did.