Wednesday 12 May 2021
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We Ask, They Answer: Q&A with comedian Jeffrey Ross

The popular comedian and host of Comedy Central’s Roasts sounds off on David Hasselhoff, his worst gigs and a love of the Chicago crowds at Zanies 

By Trent Modglin

Jeffrey Ross, roastmaster general, knows a thing or two about blistering insults. Tabbed “the meanest man in comedy” by New York Magazine and “an heir apparent to such old-school masters as Buddy Hackett and Rodney Dangerfield” by the New York Times, Ross has made a nice living making fun of people. His brash brand of comedy has taken him across the globe, from dive bars lacking a stage in the early years all the way to the silver screen, Jay Leno and David Letterman, prime-time TV and even Iraq, where he filmed an award-winning documentary about his experience entertaining the troops called “Patriot Act: A Jeffrey Ross Home Movie.” His 2009 book, I Only Roast the Ones I Love: How to Bust Balls Without Burning Bridges, is now available in paperback.

Q: What can you tell me about the recent roast of David Hasselhoff?

A: I feel like it could be the most vicious roast we’ve done. He was sort of like low-hanging fruit. But he rose to the occasion, he was a great sport, the other comedians were really funny, all his celebrity friends that showed up were really great. He actually came off really good in the end. We made fun of his singing for hours, and he came up and proved us all wrong. He sang a song at the end and hit every note. It was impressive.

Q: Some of the people who get roasted handle the pounding and up being really funny at the end.

A: That’s what you want. I feel like I like and know David Hasselhoff better now that I’ve seen him roasted. It’s like going to war together. He had thick skin and was very classy about the whole thing. I was into it. I was impressed.

Q: Did he have his legion of German fans there in the audience?

A: Yeah, I did a lot of German jokes. I’m a Jew, finally getting to roast a German. I told him the only difference between Hitler and Hasselhoff is that at least Hitler knew when his career was over.

Q: So when dealing with roasts, is it fun to find out who can handle it and who can’t?

A: It’s kind of like a football game, there’s always going to be somebody getting hurt. There are some residual injuries, and sometimes it’s somebody sitting in the stands, an innocent bystander. So you never really know. But nobody really gets offended, and when everybody leaves the roast, you want them to be saying, ‘Boy, that was fun. I hope they roast me one day.’ You want it to be a party. Hoff was having fun and everybody was having fun. He had good stuff, he had his family there to support him, he was in good spirits and it was really special. I think people are gonna like this one. … But I did manage to offend Jerry Springer in this one. I did a lot of Nazi jokes because it was Hasselhoff, and he’s so big in Germany. I made a joke about Springer’s parents being Holocaust survivors and asked why the Nazis couldn’t have killed 6,000,002. And you just see his face go white.

Q: How many of the old Baywatch girls were there?

A: There were a lot of the ex-Baywatch girls there. I told the Hoff he should have gotten a special Emmy for holding his gut in for nine seasons. By the end, he had the biggest boobs on the show. By season 11, he literally was running in slow motion. They didn’t even have to slow the film down.

Q: Last year at Zanies, you pulled up three volunteers out of the audience and roasted them for a minute each. That level of spontaneity that you show in your gigs and on roasts, is that a skill you’ve had all along or something you can actually develop?

A: I think it’s something you can develop. When I wrote my book last year, it was cathartic because as I was remembering my childhood, I realized I used insult comedy as a defense mechanism very early on. I was the boss’ son at a catering hall in Jersey, and when you’re the boss’ son, people will tease you. But I always had comebacks, and I remember that being my way of protecting myself and developing thick skin. The fact that I was taking karate as a kid also helped because it helped me develop a confidence level to where I could talk smack about people to their face. It all kind of arose and developed, so it’s not something you’re born with necessarily.

Q: Living in LA, how do you think Hollywood is different from the rest of the world?

A: Oh my god, it’s another planet. We celebrate reality TV stars. And it’s all aboutgetting your picture taken, and I feel like that’s sort of trickled down to the rest of the universe. Unfortunately, people are as fascinated as much by Snooki (from MTV’s “Jersey Shore”) as they are Julia Roberts, so I feel like we’ve lost our way a little bit as far as celebrity goes.

Q: Do you think as a society we’ve dumbed it down too much?

A: Well, I feel like we’ve been dumbing down since the minute we got smart. I think we all got really smart back in, like, 1789, and from then straight through we all stopped learning how to write and read. Calculators ruined everything, and TMZ has made us all morons.

Q: Speaking of TMZ, my friends wanted me to ask about why you seem to hate TMZ so much?

A: Well, it’s like, I’ll just be out for lunch with a friend, and suddenly halfway through a hamburger, there’s a camera eight inches from my face. Or I’ll just be leaving the dentist in Beverly Hills with a mouth full of Novocain, and there they are, asking me what I think of Lindsay Lohan’s latest stint in rehab. You’re not prepared to fire off your best material. Especially giving it away for free to TMZ. That’s one less joke for my act that people haven’t heard. When I make fun of TMZ, it comes from a certain affection. I’m not going to be a snob and pretend I don’t look at TMZ because I do. To their credit, I’m the one guy they’ve let make fun of them. One of the things I like about TMZ is that it does have a sense of humor about itself.

Q: Comedians tend to remember the really bad gigs, the bombs, when things just didn’t go your way. Do you have a memory like that?

A: I feel like when you’re starting out as a comedian, it’s so painful, there’s so much rejection. You think you’re funny but you’re really not. You’re not developed yet. I look back at those as the War Years. Now I don’t feel that way. Now, even if the joke doesn’t work, my recovery, my bounce-back, my saver is usually so funny that I can survive the bad jokes. When you’re doing the roasts, you’re trying out new material basically for the first time on national television, so you’ve learned to be sort of Teflon. You don’t even feel those bombs anymore. … Doing insult comedy in New York back in the day, I would make fun of the waiters or whoever was walking through the basement of the Comedy Cellar. It’s just something you can’t necessarily forget, but you learn to not bring with you. It emboldens you. … One specific moment…who knows? There were thousands. People would leave notes on my car window: “You suck!”

Q: You should have gone valet so they didn’t know it was yours.

A: Man, I couldn’t afford valet. Twenty bucks a show and all the chicken wings you could eat.

Q: That’s what you’d make for a gig?

A: Oh my god. I’ve done every crappy gig you could imagine. I once stood on a bar, and instead of a spotlight, they had a French fry warmer. So you just sizzled. Talk about getting roasted.

Q: What’s the worst club ever?

A: Oh man, I remember doing a show in the Catskills for Orthodox Jews. That was really a tough crowd. Nothing like bombing and then trying to get paid after. There were so many. That’s the one thing I love about Chicago, for whatever reason, and I don’t know if it’s because the winters are so cold there or what, but those Chicago folks always love insult comedy. They always want to sit in the front row, and they always want to get made fun of. I’m going to be speed roasting members of my audience, bring them up for 30 seconds of pain. I’ve gotten better at it, so I’m even more dangerous now.

Q: Speaking of Chicago, is there anything you have to do or see when you’re here?

A: When I’m Chicago, I just love to walk around. It’s great people watching. I’ll be there in October, so it’ll be warm enough. And I always find new comics, whoever’s opening for me or whoever’s playing down the street (Second City), so there’s always a lot of funny people around, and I get a big kick out of that. There’s always a bunch of crazy college kids at my shows who like to recommend bars to me.

Q: What do you think is next for you? You’ve done the road show, written a book, done some TV, the roasts and movies. What’s next for Jeff Ross?

A: That’s a great question. I’ve been asking myself that ever since we wrapped the Hasselhoff roast. I don’t know. I think I’ll take a few weeks off and emerge in September with some ideas and a bunch of new jokes. It’s a time for me to hit the refresh button and see what’s next.

Q: Have you seen the new Louis CK show on FX?

A: You know I haven’t, but everyone says it’s hilarious.

Q: It’s a blend of his routine, some documentary type reality TV and a little ad-libbed Seinfeld-esque stuff.

A: It sounds like maybe that’s the wave of the future. I’d love to figure out a TV show. But it’s all about the idea, you know? If you think of one, let me know.

Q: When you’re on the road a lot, do you even know what your schedule looks like, or do you have tunnel vision, where your agent only tells you what’s just ahead that week?

A: That’s just it. I don’t do that many dates anymore. I really do like staying in New York and L.A., writing and being behind the scenes. I do New York, Chicago and I did Montreal this summer. I’m really picky about what cities I go to now. I love the crowds in Chicago and like Zanies a lot. So these are destinations for me, not really random, on-the-road-again kind of things.

Q: What do you like the most about Zanies? What keeps you at the smaller venue when you could easily fill up a larger theatre in town?

A: I love the intimacy of the downtown club and the crowds. They’re always packed for me, and they always sell out, so that’s always a good feeling. There’s just something about the Chicago crowds. They seem to love what I do, and I always seem to rise to the occasion.

Q: I know from being at last year’s show that you’re a big fan of all the money they put into the stage decoration at Zanies.

A: I know. Where else would I be able to do 20 minutes about what a dump it is? They get people hanging off the rafters in there though.

Q: Do you feel like people always expect you to be funny, even when you’re off stage, living your life?

A:  My friends know that I can’t turn it off. I often think that I just think in insults. My brain works in punchlines. Especially after the Hasselhoff thing, I’m just in full roast mode until I turn it off. Luckily, I can defend myself. … When you’re an insult comic, you have free reign to be able to tell people to get lost or make fun of their shirt or their boyfriend or whatever. It’s fun. What I do is fun. I don’t mind it. I’m not always on, but when I’m on, you know, it really shows through. And I love it.

Q: What annoys you the most about people?

A: People who go, “Ba dum bum,” or say “That’s not funny,” or ask “Are you gonna use that in your act?” I’m always like, “You’re my act. Just be quiet. I just used it.” There’s nothing I hate than people who deconstruct comedy. Either it’s funny or it’s not funny. People say you make fun of disease or the economy or unemployment. I did a Hitler joke at the Hof roast, and people go, “That’s not funny.” Well, yes, it’s funny. In the hands of professionals, everything can be funny. That being said, Heidi and Spencer are the most annoying. Or the “Jersey Shore.” The other day, Spencer treated “I AM THE NEW WORLD ORDER” in capital letters. I tweeted back, “Then cancel my order.” And with “Jersey Shore,” I’m from Jersey, so I know when something really stinks, and those people smell.

Q: Can you imagine if someone from a foreign country thinks Jersey Shore is the norm over here?

A: No. But it does give a lot of material for us comedians. There had to be eight Snookie jokes at the Hasselhoff roast.

Q: Yeah, but she loves the attention. That’s probably a highlight for her week.

A: Only if someone’s around to explain the jokes to her.

Jeffrey Ross will be performing at Zanies, located at 1548 N. Wells Street, on Wednesday, Oct. 14 at 7:30 and 9:45. Call 312-337-4027 or log on to for ticket info. He also will be on stage at Zanies in suburban St. Charles on Oct. 15 and Vernon Hills Oct. 16.