HuffPost: How soon do you start writing jokes for each roast?
JeffRoss: Well, the way my brain works, it starts immediately when I hear the name. I can’t help it. I don’t have a filter to keep me from thinking of how to take that person on. So, I start as soon as I hear the announcement or even when they’re just thinking about that person, I start coming up with jokes in my head.
Do you ever do any deep research to dig up dirt on your subjects?
I did actually, I even talked to Selena Gomez. I ran into her and asked her for advice on roasting the Biebs, and she said, “Tell the truth. That always worked for me.”
Where does this roast stand as far as your favorites go?
Wow, you know, I never look at them that way because I have so much fun on all of them, but until I see it on TV, I don’t know. This one was more fun because making fun of Justin is almost like a national pastime. I mean, he’s an easy target. The jokes come easy. It’s like making fun of relationships or airline food.
Which person on the dais shocked you the most with their jokes?
Oh, Martha Stewart, for sure. That was insanity.
Yeah, how exactly did she wind up there?
Apparently Justin invited her to be a part of it. They had hit it off during some previous encounter — I think he thinks she’s cute. He invited her himself, as he did with most of the dais, I think.
That’s crazy. What do you think they have in common?
Well, they’ve both been to jail, so they have that in common. [Laughs]
You told me last week that Bieber had a really good rebuttal.
Yeah, his rebuttal was really funny. He told one of my favorite jokes I’ve ever heard about me. He said I looked like “the emoji for food poisoning.” And he wrote sort of an ending message, a mea culpa of sorts. It was a sincere apology in a way. He read it to me off his notebook the day before and you could tell he worked hard on it. I think people are going to like him more after this roast. I mean, I didn’t know much about him and I really came to be fond of him because of this. He took it really well and he owned a lot of his past mistakes. You’ve gotta give him credit for that.
That’s a smart move for a rebuttal. You either have to endear yourself or try to one-up everyone.
He kind of did both. It had different flavors to it. He had some killer roast jokes back at everyone and then he crushed everybody with his sincerity. I thought it was a winning effort for him. I think people are going to dig the way he handled it. I mean, what were you doing when you were 21? Figuring out how to atone for your sins? At the end of the day he’s just a young man with a big heart and a lot of fans. I just kind of saw him as a normal guy.
It sounds like being roasted might get people to lay off of him for a while, ironically.
I hope that happens, because when someone puts themselves out there like he did for this roast, I’d like to see him get a little break and some good will from it. I don’t know, he’s obviously made some mistakes but he’s also done a lot of good stuff for other people and charities, and he’s talented. He’s worth saving. I’m a believer in second chances and his fans really care about him and what he does and says, so if he sets a good example, that’s really important. Otherwise we’ll end up with a whole generation of assholes and it’ll be his fault.
One bittersweet part of seeing new roasts is remembering how great the late Greg Giraldo was on them.
Well, when you have a big target like Bieber you can’t help but miss Greg, because there would have been a real sense of honesty and truth to Greg’s roast on Bieber. I can’t help but miss him on a night like that. But you know, I could talk about Greg all day. He was not just a friend but a great comic. I thought Hannibal Buress channeled Greg Giraldo in a way, at the roast. When you see his set, you’ll see a lot of honesty in there.
How long have you been roasting people? Were you ever bullied as a kid, or did you roast others back then?
Oh I used it as self-defense against the bullies. There was a bully who was picking on everybody in my class and physically hurting people, like jumping out in the hallways and punching people in the nuts. It was just terrible, and I was even taking karate lessons but he was much bigger than me. And I remember promising myself that the next time he hit me I was going to hit him back. Then he hit me and I went down and I couldn’t even get up to hit him back, so I started making fun of him. Everybody laughed at him and he got really humiliated and never bothered me again. A young roast master was born.
That’s a pretty good origin story.
Well, I took karate as a kid and was a black belt in taekwondo at 10-and-a-half, so I feel like that gave me a certain confidence to talk smack where I wouldn’t have been able to do that.
Wow, you were a black belt?
I guess technically I still am. Even though it doesn’t fit around my waist anymore.
So, who would be the ultimate person to roast after this?
It’s funny you say that, because before Bieber, I would always just that I didn’t really have an answer, but I remember a year ago someone asked me that same question and I said Justin Bieber would be the ultimate roast, and then it happened. So, now I might as well put it out there: Kanye.
Kanye!
Kanye should be next. He’s so made, the jokes would just bounce off him. And he loves a good party. He’d be surrounded by his friends and loved ones.
And it would be all about him.
Who doesn’t love to be the center of attention, even when there’s a target on their forehead?
You have to make this happen.
Anytime and anywhere, Kanye. Anytime and anywhere. [Laughs] I’m a big fan, so it would make a lot of sense. It would be a great roast. He even has a roast theme song! What’s that one about the haters and the assholes?
He does love talking about the haters.
It would be perfect for him. He has the opening roast theme song already!
Finally, did anything crazy happen at the roast after party?
[Laughs] Well, I brought all my friends into Snoop’s trailer for an after-party party, and everything after that is a cloud in my head. It’s a blur. I do remember that Snoop was even funnier roasting the roast at the after party. Snoop is amazing because he easily could have been a comedian if he wasn’t a rapper. He has the timing and wit of a great comic. He did a lot of improvising at the roast and you’ll see some of that in the final show.
