A School Bully Got Jeff Ross Into the Roasting Business

Sticks and stones may break your bones, but Jeff Ross’ roasts hurt even worse.

Before the 58-year-old Ross erupted onto the insult comedy scene with a scorching set at the New York Friars Club’s 1995 roast of Steven Seagal, the idea that the “Roastmaster General” could be an semi-official and handsomely paid position probably never crossed any Comedy Central executive’s mind. However, as the market for multi-hour cable specials dedicated to dissecting over-the-hill celebrities through carefully honed punchlines proved to be a massive one throughout the 2000s, Ross established himself as a pivotal ingredient in the roast formula. Today, Ross is the most celebrated and booked ball-buster in comedy, without whom any roast is disappointingly incomplete.

But even before Ross gained notoriety at the members-only banquets for seasoned New York shit-talkers, he sharpened his teeth as a survival mechanism while suffering from beatings at the hand of a high school bully in his home state of New Jersey. On an episode of The Rich Eisen Show from earlier this year, Ross explained how a tough upbringing in the Garden State led him to become the only comedian brave enough to trigger Tom Brady at his own roast:

Ross also discussed his super-roaster origin story during a 2012 interview on the Canadian talk show George Stroumboulopoulos Tonight, saying of his very first roastee, “He was a big schmuck, everybody hated him. … He used to leap out of corners and whack people in the kayoonas, and everybody would just kind of like go down, and it was just painful. And him and his brother would just laugh at everybody writhing around in pain.”

“He hit me so hard. I went down, and I tried to get up to hit him back. But I just couldn’t get up, it hurt so bad,” said Ross of the attack that launched his career. “So I just started making fun of him, I don’t know what else to do. I started making fun of his forehead, a ‘fivehead’ I said. He got all flustered, and I made fun of him in front of all the other students.”

“He never made fun of me again, or anyone else at school,” Ross proclaimed triumphantly. “And a young Roastmaster was born.”

A certain man of the hour probably thought about giving Ross a pounding after Ross made that off-limits joke about Patriots owner Robert Kraft’s “massage” scandal at The Roast of Tom Brady. God knows the quarterback in question has some experience smushing balls.