Jeff Ross On Roasting Steven Seagal, Helping Trump Or Clinton, And Settling The World’s Beefs

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As he prepares to make Rob Lowe the next notch on his celebrity roast bedpost, Jeff Ross has greater ambitions for his particular brand of comedy. Simply put, he wants to settle the world’s beefs. On Monday night, from 8 to 9 p.m. ET, the man who once said of Donald Trump, “We both live in New York, we both play a lot of golf, and we both fantasize about his daughter” is teaming up with Slim Jim for “Settle Your Beef,” during which he invites fans to share their real problems with him on Twitter so he can solve them.

But his desire to help humanity goes far beyond the product once endorsed by the late great “Macho Man” Randy Savage. Ross legitimately believes that we need to laugh at ourselves and our problems now more than ever, because we are getting way too serious and offended for our own good. And he’s so serious, he tells me, that he’s willing to start with the biggest beef in America to prove that he’s the man for the job.

What is “Settle the Beef” and what are you looking to accomplish?

To solve all the world’s problems, in one hashtag. Everybody’s always arguing about everything all the time, and I feel like this is a way to make light of that and joke about the fact that we’re always arguing about everything. Even silly stuff.

Is everyone too sensitive right now?

Oh my gosh, it’s crazy! I feel like I’m living in a weird universe where everybody’s so touchy and sensitive. Thank goodness we have comedy and comedians to diffuse that. Comedy is the world’s pressure valve right now. We’d be crying if we weren’t laughing.

As the Roastmaster General, you’re someone who creates and antagonizes beefs, or at least moderates them. How do you suddenly become the man who settles beefs?

I like to think of myself as a comedic diplomat that brings people together. I was on Bill Maher’s show and I made two friends: Rob Reiner, a director and liberal activist, and Rick Santorum, who is a total conservative, almost like an evangelical conservative. I got along with both of them. I like being that guy. Not that I don’t take sides, but I like staying neutral and seeing the positives in both sides of the argument. That’s what a good diplomat does, and it’s what a comedian should do.

Are there people who perhaps don’t want their beefs settled, that would rather be eternally pissed off at everyone?

Sadly, I think you might be right. I don’t feel like the world should be that way, but there are people who just need to beef and people who need to argue, and if they don’t have somebody to be mad at, they don’t know what to do with themselves. The last thing they want to do is look in a mirror.

How would you settle the biggest beef right now: Hillary Clinton vs. Donald Trump?

It breaks my heart that I’m not moderating these upcoming debates. It’s just gonna be the ultimate roast battle for the future of civilization. I have great advice for both of them but, alas, I’m only going to help the one who calls me first. I’m a soldier of fortune when it comes to politics.

People say that Trump doesn’t stand a chance against Clinton in a straight-up debate, but does he have an advantage from being roasted?

It gives him a certain leg up, that she’s not used to being spoken to in such a blunt way. He’s basically a comedian. He can riff like a comedian, and she’s going to have to laugh it off. She says she’s not going to lower herself to his level, but the fact is this is a great American tradition. I don’t know if you saw the play Hamilton, but the forefathers roast battled and rap battled each other. That reminded me that these guys tried to debate through insults and wit, and they would duel. Luckily, today, our candidates don’t duel. No one gets killed, but there’s a certain element of tit-for-tat, back-and-forth, insult-for-insult that is a great American tradition.

Another beef that people can’t stop talking about is Taylor Swift vs. Kanye West. How would you settle that one?

That’s just a guy you don’t want to go against. Here’s the thing: Kanye, Trump… to win an argument, you have to be dealing with a sane person. You’re never going to win an argument with an insane person. That’s definitely something that Taylor needs to consider, that Kanye is off his rocker. Not in a bad way; he’s fun crazy. He’s not violent crazy, he’s just hilariously crazy. So, if I was her, I would not try to settle that beef. I would embrace his craziness and befriend him.

Your very first roast appearance was at the Friars Club Roast of Steven Seagal in 1995. That is a guy who has a reputation for not appreciating comedy, to put it nicely. How did you land that gig?

It was the mid-‘90s and roasts were not popular. They were not on TV. They were sort of a lost art. They couldn’t get any big stars at the Friars Club. They got respected comedians, like Milton Berle, Henny Youngman, and Buddy Hackett, and that’s what drew me to it. So, when I got a random call from the Friars Club saying, “We want to bring in some new blood, and we think you’re funny,” I was honored, but also kind of scared. I didn’t know that much about the roasts. You couldn’t YouTube them, so I had to go to the Museum of Broadcasting and watch these old roasts to see where the line was and how the format works. And when I saw that I didn’t just have to make fun of Steven Seagal, and I could also spar with my comedy idols, I was in. I was like, now I’m playing in the majors.

As the story goes, you put on a show that even your idols appreciated, is that right?

My opening joke was thunder. I didn’t know anybody at the Steven Seagal roast. I didn’t even know Steven Seagal. He was sitting there in his crazy karate pajamas with his ponytail, and I walked up there, I had one nice new suit that I bought to do the Letterman show. Milton Berle gave me a terrible introduction, he dismissed me as a nobody, and I was a nobody. I had a lot to prove. I shook Steven Seagal’s hand and I looked out at the two thousand people crammed into the New York Hilton grand ballroom, and I said: “I realize a lot of you don’t know me, but I feel uniquely qualified to be here today, because I’m also a shitty actor.” That was it. I felt like I found my Yankee Stadium right in that moment.

How did Seagal respond to your routine? Did you get to talk to him after the fact?

I think he was completely insulted. He didn’t laugh at all, but everyone else did, including Berle, Hackett, and Youngman. They were sort of heckling me and riffing with me, and they sort of adopted me in that moment. I got a good lesson afterward out of Milton Berle, who said, “You were great, but don’t stay on so long. Don’t steal my thunder. They only remember the home runs.” After that, I tightened up my roast sets to just be home runs.

After all of these years, and after all of the roasts and being considered the best at what you do, is there any celebrity or personality out there who still has a beef with you?

If there is, I hope they tweet me and settle that beef when I do this Twitter party for Slim Jim. If there are, they’ve never come forward. Buddy Hackett warned me about this a long time ago. He said, “If you piss somebody off, you’re never gonna know it. They won’t ever call you or see you or work with you. They’ll be silent about it.” So, if there’s somebody out there, please step forward. This is your chance. Let’s settle the beef. I’m looking for all comers. And if that person is dead, I hope a representative from his estate will tweet me.