Ross is a standup, an actor and a writer, and he once directed a documentary, but he is best known for being an insult comic, in the school of Don Rickles. In addition to his continual presence on the Comedy Central roasts, he has ascended to the rank of Roastmaster General in the Friars Club, the organization of entertainers who held the first roast in 1949 (the guest of honor was French actor Maurice Chevalier.) In other words, to be roasted by Jeff Ross is a privilege, even if it feels more like a punishment while it’s happening.
As Ross’s new Comedy Central show The Burn launches this month—a weekly series wherein he picks apart pop culture, politics, and whatever else is going on in the world—he took some time out to educate Co.Create on the finer points of adding insult without (serious) injury.
Roast jokes tend to be shorter and more to the point than other kinds of jokes. They‘re more based in fact, and they’re economical. The fewer words the better. Coming up with them is almost like a mental exercise that affects your body. Saying things out loud that normally you’d say behind people’s backs. A true roastmaster just lets it fly. That’s why I never prank people. That’s behind their back or sneaking up on them, and catching them off guard. I’d much rather confront them and tell the jokes face to face. That’s just more honest.
The best person to roast is somebody who can take it. Somebody who’s got a good reputation and has earned the right to laugh at themselves. The Roseanne roast was a fun one. Although I loved her TV show when I was young, the real attraction for me was her unapologetic brand of stand-up comedy. I always love comedians who don’t hold back, who go for it, so I thought my jokes about her should be brutal. I thought I’d be doing her a disservice if I held back, so to me this had to be one of the more brutal roasts, as a way to pay respect. I handed her an apple and I said, "Usually when I roast a pig it has an apple in its mouth." She threw it right back at me.
Roasts are one of the few safe havens comedians have these days. From my standpoint, I take advantage of that. Why have a big piece of cake if you’re not going to eat it. I love pushing it. That’s what roasts are about. Roasts bring people together. They keep the conversation going on certain subjects that don’t always get talked about.
I think it helps to praise too. Backhanded compliments can bridge the gap. I only roast people who I respect and I’m a fan of—people I love. If you do that, the praise comes naturally, so it’s not something that has to be carefully considered. Roseanne deserves praise; just the fact that she sat there and took the jokes. Plus, she has such an amazing career behind her and all kinds of new adventures in front of her.
You want to make jokes about something that everybody knows about that person. What are the lowest common denominators? When I’m doing one of the Comedy Central roasts, sometimes I even hang up pictures of them around my house or office, just to get me in the mindset. You know, "what do we all love about _______?"
To see how Ross would handle a few famous names, click through the slide show above.