Jeffrey Ross interview

I've always loved roasts. Some of my earliest comedy memories are of the Dean Martin roasts. I looked forward to every one and it was probably the start of my non-laughing. Oh how I'd hate when someone in the room let out a mighty guffaw and I'd miss the follow-up joke.

Those roasts were tame (they were on network TV, afterall) compared to the uncensored stuff we get on Comedy Central these days. And if you spend some time on YouTube, as I did the other day, you can find lots more non-televised ones (or at least we don't get them up here).

I spoke to Jeffrey Ross the other day ahead of his upcoming shows on Friday and Saturday at the River Rock Casino Resort and Red Robinson Show Theatre respectively. He's been dubbed the Roastmaster General for his skewering over the years. He's hilarious. You could spend hours watching him on various roasts over the years. And you wouldn't regret it. In fact, go do it now. I'll wait...

You back? Good. Now enjoy the article I did on him in the Province newspaper. I'll wait...

Okay. Now go ahead and read the full interview I did with him.

Jeff Ross – June 3, 2011


"I think nothing’s off-limits, honestly. If you’re a really good joke-writer, I don’t think anything’s off-limits. You’ve seen the great roasters go for the jugular. And if you can make that subject laugh at themselves, you’ve got a real victory there." – Jeffrey Ross

Guy MacPherson: Hello.
Jeff Ross: Hey, it’s Jeff Ross. How you doing?

GM: Hi, Jeff. Thanks for calling.
JR: Oh, man, thanks for doing this.

GM: I hear wind. Are you outside?
JR: Yeah, I’m at the beach. I’m at the Jersey shore right now. It’s beautiful. I’m about to go on in a couple hours in Atlantic City.

GM: Have you ever played Vancouver before?
JR: I have... never played Vancouver before. I’ve been to Vancouver and I love it.

GM: What have you been for?
JR: I’ve been there for bachelor parties. And that’s almost as fun as performing.

GM: You’re coming here with the Just For Laughs Nasty Show. Is that something you’re going to be doing in Montreal later this summer?
JR: Yeah, a very similar show, I think. I guess it’ll be a try-out for Montreal, which I’m really psyched about. I really love it there. I don’t know why but they have the greatest comedy crowds ever in Canada.

GM: Have you done the Nasty Show before?
JR: No, I’ve never done the Nasty Show before. I’ve done other shows where I roast Montreal and different sorts of crazy experimental shows. I showed a documentary at the festival one year that I made about my trip to Iraq. So the Nasty Show is something totally new for me. I guess last year Greg Giraldo hosted it, who was a good buddy of mine who past away. So I was honoured to be asked to take over that this year.

"When you think up a good joke you can’t wait to get up there. There’s always a temptation to give it away beforehand but then I lose the punch of the live show. So it’s a little bit of a Catch-22 for me because you want people to know how much fun it’s going to be but you also don’t want to blow your load." – Jeffrey Ross

GM: Do you go out of your way to nasty it up and be offensive or is that just your regular act?
JR: That’s interesting. You know, I don’t know. I think I’m going to have to feel the room. I don’t know. I don’t consider myself nasty; I consider myself classy. But maybe a little nasty. So this’ll definitely be new ground for me. I feel I’ll have to turn it up into something a little harder than I normally do. Which is hard to do because I’m pretty hard normally.

GM: When I saw you in Montreal in 2005, you weren’t then known as the Roastmaster General, or a roaster at all, were you? When did that come about?
JR: The birth pangs of the Roastmaster General title was something that happened around then. I think it really took off full throttle around 2005 when I roasted Pam Anderson on television in America.

GM: Was that your first one?
JR: No, I’d been roasting since the mid-nineties but it was a little bit more underground. It started to take off around 2005 into being our new national pastime here in the States. People love roasting. So I’m going to try an experiment at the Nasty Show, which I don’t think has ever been done before in Vancouver. I’m going to try speed roasting volunteers from the crowd. Whoever wants to come on stage to get ripped on. Fifteen seconds of pain.

GM: Will you look at certain prototypes of their build? Or maybe you have some jokes hidden away.
JR: I think it’ll just be summing up people’s essence as they stand there. I’ll do brief interviews right there on stage with whoever wants to come up. It should be very chaotic. Let’s call it planned chaos. Hopefully the venue will hire some extra security in case it gets nuts.

GM: There’s a real art to roasting, isn’t there?
JR: I think there is. I feel like there’s a lot of guidelines to make it go well. You don’t want to be a bully. You don’t want to pick on people that aren’t up for it. You want everyone to leave the show going, ‘That was so much fun. I wish I’d been roasted.’ To me, that’s the key, is to have everybody think of it as a party and not as competitive or mean.

GM: Have you seen it gone wrong before?
JR: (laughs) In what respect?

GM: A lot of people really get it – how to do it well without crossing a line that is maybe more hurtful than funny – and maybe some don’t get it.
JR: I’ve been really lucky in picking targets that are good sports. I feel like I haven’t really hurt anybody. But then again, the great Buddy Hacket once told me that if you hurt somebody’s feelings, they’ll probably never tell you about it.

GM: Have you seen other people roast where you think that probably wasn’t the way to do it?
JR: Oh, for sure. Mostly in the hands of amateurs. Every now and then Comedy Central will invite an amateur to the roast. For instance, the Situation from The Jersey Shore at the Donald Trump roast. You can see how in the hands of beginners it can go horribly wrong.

GM: Doesn’t he get help with it, though?
JR: You would think. But, you know, some people are special-ed students when it comes to roasting.

GM: What is off-limits when you’re roasting?
JR: I think nothing’s off-limits, honestly. I feel like if your joke is funny and well-crafted, people consider it a back-handed compliment. So if you’re a really good joke-writer, I don’t think anything’s off-limits. You’ve seen the great roasters go for the jugular. And if you can make that subject laugh at themselves, you’ve got a real victory there.

GM: What was your favourite one to be a part of?
JR: My honest answer is whoever’s next. Because I love the preparation. Before I get to Vancouver I’ll start writing jokes about the city. I like the going-into-battle feel of it, sharpening my pencil and honing my ideas about a certain subject. So to me the prep is the really fun part. The audience will see the payoff, which is also really fun, but the whole quote-unquote “getting ready”, that’s where the real excitement is for me. When you think up a good joke you can’t wait to get up there. There’s always a temptation to give it away beforehand, like for instance in your newspaper, but then I lose the punch of the live show. So it’s a little bit of a Catch-22 for me because you want people to know how much fun it’s going to be but you also don’t want to blow your load.

GM: It’s interesting that your stand-up has evolved into a roast of various elements like the city or whatever. It’s still a roast even though it’s your stand-up.
JR: That’s right. Roasting for me has gone beyond celebrities and tuxedos. Now I can roast people, places and things, adapting it to the world. The world is my dais, if you will.

GM: You’re also the Roastmaster General of the New York Friars Club, is that right?
JR: That’s actually an unofficial title that I believe was first said by Jimmy Kimmel at the Pam Anderson roast, although he claims it wasn’t him. He heard it somewhere. It’s a take-off on the Toastmaster General, which was a take-off on the Postmaster General.

GM: So there are no duties involved with being the Roastmaster General.
JR: Thick skin and a willingness to work for free at the Friars Club roasts.

Charlie has a really, really great sense of humour, willing to laugh at himself and own his history. People talk about his character but the guy I met was very sincere, very good to his friends, and was trying hard to get his kids back in his life. He seemed sober and in a better place when I met him. – Jeffrey Ross

GM: What is the status of the Kid Rock roast?
JR: They’re not going ahead with it, sadly. I was really disappointed but I guess it didn’t work out.

GM: Is there somebody else that you know of?
JR: No, they haven’t mentioned anyone. They ran some names by me. They ran one name in particular by me that I’m not at liberty to say yet, but if they can secure this roast it’s going to be the greatest of them all.

GM: Charlie Sheen?
JR: I’m not going to answer that. That would be a really, really great one.

GM: It would be. I read that you did some shows with him roasting him. Boy, we could have used you in Vancouver.
JR: Man, I was scheduled to go up that day and I got a last-minute call saying they didn’t need me. I was really disappointed. I was really, really disappointed.

GM: I think they did need you. I don’t know what they were thinking.
JR: Yeah, that was a heart-breaker because I was really psyched to roast him in a foreign country in front of thousands of people. Those shows were really fun.

GM: He would be perfect for a Comedy Central roast. He seems to have a good enough sense of humour about himself that he would allow it.
JR: Yeah, Charlie, to his credit, has a really, really great sense of humour, willing to laugh at himself and own his history, if you will. People talk about his character but the guy I met was very sincere, very good to his friends, and was trying hard to get his kids back in his life. He seemed sober and in a better place when I met him.

GM: Was there anyone who was really tough to roast? Anyone you had a hard time getting a handle on for whatever reason?
JR: Ah, that’s a great question. I feel like every time Comedy Central announces the new roastee, I start to panic and go, ‘That’s so hard! There’s been a million jokes already about David Hasselhoff and Donald Trump’s hair and Flava Flav’s clock. How are we gonna do this? It’s going to be too hard.’ And then, of course, inevitably we puff a little medicinal and the next thing you know you’ve got ten minutes of material.

GM: (laughs) Is that how the process works?
JR: It will in Vancouver, I’ll tell you that much. (laughs)

GM: Part of the fun of the roasts, too, is not just the person of honour but of course the whole dais.
JR: Yeah, anybody who’s up there is fair game. At the Vancouver shows I expect it to be a little bit of a lion-tamer circus situation where I have people coming at me from all sides. I feel like I’ll need a machine gun of jokes to handle this one.

GM: What is the format going to be? You guys are all coming up separately, right?
JR: Yeah, but I’m hosting and they’ve asked me to do this speed-roasting. I’ll do an opening monologue about Vancouver and I think I’ll just start ripping into people because it’s the Nasty Show. I feel like this is a license to kill if there ever was one. It’s finally a chance to break down my wholesome image.

GM: Oh, yeah. You are, I think, a very decent, good guy. It’s kinda like Rickles. He’s known as an insult comic but just the sweetest prince of a man off-stage.
JR: I saw him recently at a party at Jimmy Kimmel’s house and Rickles was just holding court. He’s like the grandpa of comedy right now. Everybody just wants to have a connection to him and to have a moment where he acknowledges you by making fun of you. That’s just the greatest.

GM: And did he get you?
JR: Oh, yeah.

"If you read my book, chances are you’re not going to get picked on. I recommend it as a text book for children. Except the parts where I fucked Bea Arthur." – Jeffrey Ross

GM: You have a real respect for your comedic forefathers, don’t you?
JR: You know, I’m sitting here on the Boardwalk in Atlantic City where I saw Don Rickles perform, I saw Buddy Hacket perform before I knew them. So yeah, I guess I have a real affinity for the roastmasters who came before me.

GM: I always liked Milton Berle even though I was a kid and he was ancient. You hear some younger comics who dismiss the old style that they don’t maybe get or is not in vogue anymore.
JR: Milton taught me a lot. The things that he taught me will always be in vogue. He was very classic. After my first roast I asked him for advice and he said they only remember the home runs. So I try to do the best jokes and really just drop the A-bombs thanks to Milton’s advice.

GM: Do you think comics need a sense of history of their craft?
JR: It’s an interesting question. Some do and some don’t. There’s plenty of people who don’t want to look back who think comedy is supposed to break new ground all the time. And maybe it does in its message but in the delivery of it, in the presentation of it, I feel like those methods are pretty timeless. Until someone learns how to tell jokes out of their rectum, it’s pretty much a guy and a microphone and a spotlight and an audience. Booze helps, too. And in Vancouver a little medicinal will probably help the jokes.

GM: (laughs) For who? The audience or you?
JR: Both.

GM: Have you danced since Dancing with the Stars?
JR: Oh, my gosh, of course.

GM: Were you a dancer before that?
JR: Oh, yeah. I won a dance competition in summer camp when I was about seven. I’ve been dancing ever since. I’m a maniac.

GM: So then what happened on the show?
JR: I got poked in the eye on the season premiere. I had a scratched cornea. I danced against doctor’s orders. I danced poorly and I got the lowest scores since Heather Mills’ fake leg flew off.

GM: So if you hadn’t been injured, you probably would have gone all the way?
JR: I would have at least made the finals, I’m convinced. I danced so poorly people thought it was a telethon and sent in money.

GM: Did you really try to lobby to become an American Idol judge?
JR: I really thought there was a chance. That’s how ridiculous I am. I was convinced that they needed somebody in the Simon seat, somebody who could tell the bad ones that they’re bad, straight up with honesty and a little bit of tough love. But obviously the show has tanked without me.

GM: Is there another kind of TV project you’re working on?
JR: I’m working on a Comedy Central show which will be in the roast world but not exactly a roast. I think it’s going to be really special. We’re going to shoot that this summer. It’ll be a pilot. I’ll be warming up for that this summer by doing shows in Vancouver and Montreal and getting as much stage time as I can in front of great crowds. I’ll take some of the themes I’ll be talking about in my stand-up into a TV pilot.

GM: I see on Monday you’re going to be on The Bachelorette.
JR: Yeah, is that airing already? How did you spot that? They haven’t even told me that. It was really fun, man. Taking the roasting into new environments. I’ve roasted on Dancing with the Stars, now I’ve roasted on The Bachelorette, I just did a part on Family Guy where I roast one of the characters. It’s beyond my imagination what roasting could be.

GM: How does something like that happen? Did you approach the producers and say, ‘Hey, how about this?’
JR: Oh, no, it was totally their idea. They had read my book about roasting and giving tips to amateurs for throwing their own roasts. So one of the producers tracked me down and said, ‘Would you be interested in throwing a roast of the Bachelorette?’ And I was thrilled. Who cares if you piss her off? If she’s gonna cry, you just get more camera time.

GM: Did you help the bachelors with the writing of the jokes?
JR: I actually coached them beforehand on tips for making a woman laugh. If you can make a woman laugh at herself you can virtually make her do anything. I think that’s an old Marilyn Monroe quote. And it worked. I feel like she was very enamored by a couple of the guys who were on the funny side. Funny guys often do better than good-looking guys with the chicks.

GM: Yeah? You think so?
JR: I know so.

GM: I thought they just laugh at anything a hot guy says even if he’s not funny.
JR: I laugh at everything every girl says.

GM: That’s a good rule of thumb. Who are some of the best roasters you’ve seen, now or through history?
JR: The classics, the legends that we talked about but you could probably add Ronald Reagan and Foster Brooks and Dean Martin to that list. There’s the Mt. Roastmore, if you will. Hacket, Henny Youngman...

GM: And who are some of your favourites today?
JR: Oh gosh, today I love watching Lampanelli, of course, and Whitney Cummings. We have Anthony Jeselnik on the roasts now. He did great. He used to write for the show, like Whitney, and to see them jump up onto the big dais is really fun. You always want the shows to be as good as possible and have new faces just to break it up, to have new people to make fun of.

GM: When Giraldo died, I first thought the roast might die with him, but they go on through history.
JR: Yeah, these roasts have been around a long time so I feel like it’s only going to get bigger for a while and then probably get corny again. And then one day some guy’ll come along and it’ll get even bigger. It’s a part of our culture. Americans just love – and I believe this goes for Canadians as well – it’s like the public spectacle. It’s like a public hanging. You love to see the big fish with a target on his head.

GM: You mentioned the back-handed compliment. I’m a big fan of the back-handed compliment when done right.
JR: Oh, yeah, that’s the key. You want to roast people that are very established so sometimes you have to sort of kill them with kindness before you really get to the hard stuff. It’s like a spoonful of sugar helps the medicine go down.

GM: Why do you think roasting is important for everyday real life? Or do you?
JR: Yeah, but not every day. I feel like roasts are special. And you have to take your time putting them together and the roastee, the honouree, has to feel very protected. They have to feel like the man. You want everyone to feel like they’re Frank Sinatra surrounded by the Rat Pack. You don’t want them to feel like a deer about to get shot.

GM: What about when you’re just hanging around with your family or friends and you can incorporate some of that roast flavour into your everyday life?
JR: Well, I have to because everybody expects me to. Every guy in the airport wants me to rip into them. But I feel like it’s a good self-defence mechanism. If you read my book, chances are you’re not going to get picked on. I recommend it as a text book for children. Except the parts where I fucked Bea Arthur.

GM: What?! I missed that.
JR: It’s in there. But it’s not true.

GM: Okay, Jeffrey, I think you’ve got another interview lined up.
JR: Yeah, I’ve got another interview for a different show.

GM: Well, it was great talking to you. I look forward to the show here.
JR: I had fun. And your questions were great. Thanks for getting the word out.