Editor’s Note: On September 10 at 11pm ET, Comedy Central will air Jeff Ross Roasts Cops. So because that’s happening, we think you should read/reread this interview we did fairly recently with Mr. Ross in which he talks about spending time with Boston’s finest, plus other amusing topics, like Donald Trump and pro wrestling. Have fun!
Every man has one great talent. Jeff Ross’s talent is telling hilarious jokes about other people–right to their faces. He has parlayed this skill into becoming America’s undisputed Roastmaster General, skewering everyone from William Shatner and Bob Saget to Justin Bieber and even the incarcerated on Comedy Central specials.
Recently, Ross made time for me while doing some publicity for Slim Jim’s new campaign, Settle the Beef, to talk about Donald Trump, hair loss, beef jerky and roasting police officers. And trust me, he went deep, he went hard, and he went big. (Note: If you’d prefer to digest this interview in audio form, check it out on the Made Man Podcast Ep 7 here.)
“Trump laughs at everything, except when you make jokes about his finances. I made jokes about him wanting to make love to his beautiful daughter. It’s only when I made a joke about his book having four chapter elevens that he got mad. He’s a strange one.”
You’ve been roasting people for more than a decade. Have you ever gotten your ass kicked after making fun of someone that just didn’t really like it?
[Laughs] You know what, here’s the thing. I’m a black belt in taekwondo and that gave me the confidence to talk smack to people, and I think I take it right to the line. And although we are roasting Rob Lowe in a few weeks, I don’t think he’s gonna take a swing at me, but I’m very careful about picking targets who can take a joke. That’s the most important thing. You want everyone to leave these roasts thinking that was really fun. Now if anything, he might try to make love to me, but that’s about it.
He doesn’t want you to mess with the face.
I feel like roasting brings people together. I feel like I make friends at these roasts more than adversaries.
Oh yeah! Snap into a Slim Jim. You got some big wrestling boots to fill there, my friend.
Hey man, maybe I should dress up like Macho Man for the next roast.
You totally should.
Fans would love that. Well, roasting’s the new wrestling in a way, so it kind of makes sense. I like anything that involves meat. I’m a big meat eater. I eat meat every day. It’s just a fact. So when they came to me, it made a lot of sense. Plus it’s also about settling the beef, that’s their new campaign, which I feel like is kind of what roasting is too. Telling the truth, putting your opinion out there, not in a bullying way but in a very honest way and funny way.
Right. So do you have any big beefs currently?
Right now I’m probably in a safe place where nobody’s too mad at me. I don’t have any big beefs, but I feel like our world is constantly beefing with each other, whether it’s politics, religion, war. I feel like comedians right now are kind of shining a light on all of the darkest things in the world and making people feel better. I get a lot tweets about people saying there’s so much pain in the word, tell more jokes. So I try to keep that at the top of my head, but no real rivals right now.
You’ve done a couple of roasts of Donald Trump and he is apparently sensitive about how much money he has.
Isn’t everyone sensitive about money? So I don’t blame him, but Trump’s a good sport. I’ve roasted him twice, I’ve been on his airplane, and I’ve done shows at his Mar-a-Lago compound, whatever it’s called, hotel, resort. And he laughs at everything, except when you make jokes about his finances. It’s very strange. You could make fun of his family, I made jokes about him wanting to make love to his beautiful daughter. I made jokes about his hair. I made jokes about just about everything you could possibly do to hurt his feelings. It’s only when I made a joke about his book having four chapter elevens that he got mad. He’s a strange one.
Were there any jokes that you wanted to tell but couldn’t end up telling? Do you have any leftovers that you’d like to share now?
I don’t think there are leftover Trump jokes. I think the beauty of Trump is that he’s almost like a comic’s comic. He tells jokes almost by accident and then we make jokes from there. He could be our first orange American president.
Yeah he would be breaking boundaries there.
You have to admit, President Obama has really broken down barriers for people of color. Donald Trump is clearly orange. They won’t even play “Hail to the Chief,” it will be “Oompa Loompa Doompety Do.” In a weird way part of me wants him to get elected. As Roastmaster General, I immediately get bumped up to a Cabinet-level position. He’s gonna need a lot of insults about foreign countries for his Twitter account. Who better to write those than me?
You could be like head speechwriter.
I feel like he’s gonna need me. I could help both of them win the debates, so if either Hillary or Trump is reading this, call me before the other one does. I’ll help you guys settle the beef.
If you were writing jokes for Hillary, what would your joke be?
Oh, I’m not giving it away to you, Made Man. Are you crazy? The world is in flux. I have to save those for when I have a private sit-down with one of those candidates. But I think she needs to laugh it off. I think when he comes at her, she needs to laugh and treat him like any other reality star and it will be the best debate in history.
“Part of me wants Trump to get elected. As Roastmaster General, I immediately get bumped up to a Cabinet-level position.”
I’m sure a lot of guys reading this want to roast their own friends. What are your tips for them, as the Roastmaster General?
Don’t bully people. People have to volunteer to get roasted, that’s number one. That avoids physical confrontation. Backhanded compliments, those always work best. Build somebody up before you take them down. Never roast on an empty stomach. I highly recommend beef jerky original flavor to keep you from getting low blood sugar while you’re doing a roast. ’Cause if you start forgetting your jokes halfway through, you’re screwed. So I always eat right before I do a roast. Otherwise I start to lose my mind.
I would say dress up a little for a roast. It’s easier to say mean things when you look kinda dignified. I think Trump could vouch for that. And go deep. Don’t bring a knife to a gunfight. Go deep, go hard, go big or go home.
Those are great tips. So speaking of knives and guns, I heard you spent time with some police officers recently and roasted cops.
It was really intense. They were a really tough crowd. Cops are really brave and a little crazy and I’ve always respected cops, and to see so many people hating on the cops lately was tough for me to watch—all these protests—although they make a lot of good points. I felt like no one was talking to the cops, they were just talking about them.
So I put it out there that I wanted to roast a major city police force and they all said no except one, the Boston Police Department, where they’re doing things right right now. No cop has killed an unarmed person there in 25 years, so they stepped up with their good record, they let me come in and roast them, and I learned a lot about cops.
It airs September 10 on Comedy Central, Jeff Ross Roasts Cops, and spoiler alert, I survived. Although they don’t laugh at all the jokes, and every single joke I made about the cops, they laugh at and then they mumble something under their breath as you might expect. They always have to have the last word. And I did one roll call where I completely bombed. Like, one thing about cops is that you can’t bother them while they’re working. A couple months later, I went back and invited them all to a comedy club, got them a few beers and suddenly they were a great crowd.
Have you ever bombed really bad roasting someone?
You know, I got about five or six roasts into my roasting career and I was like, “Alright, this will be the one, this will be the one where I bomb, this will be the one that takes me down. I’ll lose all my credit, I’ll lose respect,” and then it just hasn’t happened, buddy.
I kept swinging, I kept getting better at it, kept writing better jokes. Every now and then a joke misses and you feel bad or you feel awkward, but I can’t say I’ve bombed. A joke might bomb, but I don’t bomb. My bombing days ended the minute I stepped up to a roast podium. Once I had that podium in front of me, it was like having superpowers. I feel like I could say anything and get away with it.
Have you ever been roasted?
I’m afraid. I’d cry, forget it, not a chance, no way.
It seems natural that at some point…
I can’t believe no one’s asked me! If they asked me, I’d probably say yes. No one’s ever asked me. Friars Club never asked me, Comedy Central never asked me, no one’s ever asked me, and I feel like it would be the biggest roast in history because who deserves it more than me? They would line up. It would have to be a three-part miniseries.
I would get demolished. Especially looking like Bruce Willis if he drowned. I mean, I’d probably go first and do all the meanest jokes about myself, and then let them have at me. No one’s ever asked me, and believe me, it’d be A-list comedy, they’d have everyone wanting to roast me. I think Joan Rivers would come back to the grave to roast me. Charlie Sheen’s first time out of the house all year to roast me. I feel like Hillary and Donald would both quit the race just to come to that roast.
Can I be like an associate producer on that since it was my idea?
I think it’s your idea, yeah, you’re the first person to ever think to roast me. Come on, give me a break. No, I’m just kidding. I’ve never been roasted. It’s a good idea, you’re a co-EP on this one.
Oh great! I’m gonna quit my job.
You call this a job?
Not this job, I have this landscaping gig part time. I also thought you would’ve been on Comedians in Cars Getting Coffee by now, but you haven’t.
I know, what’s going on with that? I’m like the only guy. They’re like up to people who aren’t even comedians. I’m a little insulted. I haven’t been asked and I have perfect five-star Uber rating, so you’d think that Jerry would step up and find me, but no. Jerry, if you’re listening, I need a ride.
“My bombing days ended the minute I stepped up to a roast podium. Once I had that podium in front of me, it was like having superpowers.”
Do you like coffee?
I like coffee, I like cars, and I like Seinfeld. I’m a perfect fit.
Maybe he’s afraid.
Maybe he’s afraid. I don’t know. Maybe. It’s OK. It’s a funny show though. The one with Mel Brooks and Carl Reiner was my favorite.
OK, I’ve got two more questions.
What you got?
Apparently this month is National Hair Loss Awareness Month and I feel your pain, I’m losing the battle as well. I thought it was interesting that you just decided to shave it off a couple years ago. Was that a tough decision?
No, you know what, I did it on a whim. I was leaving the next day to host the Oddball tour and it was 95 degrees in Tampa and I was gonna be outside hosting a four-hour show and I had a long curly afro that was just always sweating and up in a man bun. And on a whim, as a joke, my buddy, my barber, Big Greg on Melrose, said, “Just shave it, dude, your chick quotient will go through the roof! ’Cause everybody’s gonna wanna touch your head.” So I just did it and now I look like Lex Luthor’s accountant. It saves me a lot of time in the morning, I kinda like it. I just kept it and I don’t know, I feel like people take me more seriously this way. What do you think?
I agree. I think it looks great. You’ve been rocking hats more, you got a really good hat game going.
The hat thing’s huge. It’s been really fun because now everybody gives me fedoras. I look fedorable.
It’s a classic look. You sort of look like an old-school comic now.
I feel like that, and I get to wear headbands and hats and we have a roast coming up, so they’ll be making fun of my head instead of my face for a change. It’s really a way to divert the comedy from my career and my personal life to my physical appearance, which I can handle much better.
Yeah, smart. Alright, last question. Do you have a roast joke you’re most proud of?
I feel like one of my favorite jokes ever is about Trump. I’ll just put it out there ’cause people repeat the joke to me all the time. Donald Trump’s ego is so big, he videotapes himself masturbating and then masturbates to that video. This is a guy’s joke.
That’s funny because it actually might be true.
It’s very possible that WikiLeaks will release that video at any moment.
Alright, Jeff Ross, this was a blast. Thank you, sir, for taking some time out of your day to chat with us.
Dude, thank you for getting the word out on everything I’m doing. I really appreciate it too.
To listen to this interview in audio form, check out the Made Man Podcast here.