Cranking up the heat with Jeffrey Ross, Roastmaster General.
By John Bolster
Welcome to our Jeffrey Ross article—you look great, you mouthbreathers. How long did it take you to shave your palms this morning? Jesus. Hey, Jeff, nice fans you got here. You have a book coming out? Wow. It better be a pop-up book, because these CroMags sure as shit can’t read. Seriously, readers, you do look great. Take off your tan trench coats and stay a while.
What can you say about Jeffrey Ross that hasn’t already been scribbled about him on the wall of a Jersey Turnpike rest-stop men’s room? And man, is he ugly. Jeff Ross looks like Donnie Wahlberg and Droopy Dog had a baby and fed it bong hits. Hey, we’re not saying Jeff Ross smokes a lot of weed, but during our interview we could’ve sworn we heard Willie Nelson in the background saying, “Ross, quit bogarting.” No? Hey, we don’t even do comedy; we’re just here to put the commas and semicolons in the right places.
But if the roasting chops exhibited above are any good at all, well, they were learned at the foot, or, more accurately (and less stinkingly), from the new book of the Roastmaster General himself, Mr. Jeffrey Ross. I Only Roast the Ones I Love is out this month, and it’s not only an entertaining and unexpectedly moving memoir, it’s also a how-to book for roasting. The master reveals his jokewriting secrets and roasting tips so you, the nonprofessional comedian, can stage your own roasts and learn how to bust balls without burning bridges, as the book’s subtitle goes.
We prank-called Ross recently and got that fat fuck to spill his guts on everything from saving Courtney Love’s life to Tom Cruise’s peacemaking skills to being orphaned at 19 (he was) to his objection to flip-flops on dudes, and many, many of the man’s other deep pathologies. Against all odds, we actually had a great fucking time.
Your book is a combination memoir and how-to book for at-home roasting. Are you concerned that the amateur roasting could go horribly wrong, like those backyard wrestling incidents you see on YouTube?
[Laughs] I hadn’t thought about it going wrong, but I guess there’s always that danger, you know? You have to be very careful. Roasts are like space launches. One element isn’t right, and it’s a catastrophe. One drunk astronaut, and you’re fucked.
Who’s been the easiest person for you to roast, so far?
I gotta go with Flavor Flav. That one could have been a three-part miniseries, since he’s almost a punch line already. My opening joke was, “How do you embarrass a crackhead who wears a Viking helmet?” And I just took it from there.
Who’s been the scariest to roast?
Warren Sapp. When I roasted him on Dancing With the Stars, I thought there was a chance he might rip my head off. But in the end I realized he was just using his jock-talking-smack kind of approach to try to psych me out a bit. But the truth is, he took me aside and said, “Don’t hold back. I want you to really bring it.” So it was a little scary for a second, but he took it pretty well. I told him, “I used to think you were on steroids, then I realized you’re just fat.”
Is there anyone out there you’re dying to roast?
Obama would be the greatest roast ever. Because the ones that are obvious targets—like Flavor Flav and Pam Anderson—the ones I’ve done, they’re fun, but the challenge is when you get somebody you don’t hear a lot of jokes about. To me it’s all about him whipping out his stimulus package and banging it on the table. I heard Obama’s dick is so big he calls it Air Force Two.
You take credit for turning Courtney Love’s life around. Can you tell our readers about that?
Well, she was headed down a slippery slope—and I’m not talking about Pam Anderson’s vagina—and she needed to be stopped. I felt a sense of urgency that I could roast her into rehab, and that was my goal. She was definitely partying very hard that night, and she had a reputation, and we were scared. I took it upon myself to try to save her life. And I did it in one fell swoop, with one well-crafted zinger. I said, “How is it possible that Courtney Love looks worse than Kurt Cobain?”
You talk about how one of your idols, Buddy Hackett, always knew where the line was, and never to cross it, but that joke—except for the fact that it was used as a kind of intervention— seems like it is over the line.
Yeah, but I don’t feel like I crossed it. Because first of all, she wasn’t present. It wasn’t like I was saying it to her, because she was completely out of it. So in essence, I was saying it about her. And when she saw the reaction in the room—there was a gasp! And then an explosion of laughter. And Courtney Love looked at me, she looked at Pam Anderson, she looked at the crowd, and then she sort of looked within herself. And now she seems like she’s doing better, and I have to take credit.
You describe another incident in which Tom Cruise shows up at Jimmy Kimmel’s house to watch football and ends up settling a long-standing feud between you and Cousin Sal. [Cousin Sal had pranked Ross via text message when Ross was competing on Dancing With the Stars, sparking a bitter feud.] Tom Cruise—who knew he was Solomon?
[Laughs] I’m sure he would love that.
So that was all true, blow-by-blow?
Tom Cruise broke it down. He was nothing short of the greatest legal mind I’d ever met. I think, at first, he was a little taken aback by the whole thing. We kind of dropped it on him. I don’t think he came there to talk about Dancing With the Stars. But in the end he made peace between two warring factions. And I think he got a certain pleasure from the whole thing. He was really useful, really helpful. I think he saw the pain—or rather he sensed the pain in my voice—and he saw that Sal and I were really good friends who had had a really bad fight, and he wanted to help. And thanks to Sarah Silverman for moderating, and to Jimmy Kimmel for … cooking. It actually winds up being one of the more uplifting stories in the book, and in my life.
Is there a cap on the number of “Abe Vigoda is dead” jokes that are possible? You’ve gotten unbelievable mileage out of that.
[Laughs] I’m not gonna lie to you. I am nervous about him, because my good friend Bea Arthur passed away after I finished the book. So now it’s like, “Oh, boy, we’re on the verge with my last living punch line.” I’m a little nervous for my favorite muse. But Abe Vigoda jokes are kind of like grains of sand: Each one is different, and there are millions and millions of possibilities.
You were suddenly on your own at age 19, after both your parents passed on. What do you remember from that time?
I remember not feeling sorry for myself. I remember just taking it as it comes. I don’t know where that comes from. Maybe it’s just a survival instinct that humans have, or maybe I’m just lucky that my parents prepared me to be on my own. I remember it being shocking and sad, but then also oddly liberating. Because suddenly I’m parent-free at 19, you know? You could bang a Chinese hooker on the kitchen table, and no one’s there to tell you to go do your homework.
There’s your silver lining.
That’s the silver lining of being an orphan. You see all these documentaries about orphans, but hey, look at the bright side. I try to think positive.
You have a pet peeve about dudes and flip-flops. I agree. When I see guys wearing flip-flops in the city, I think, Do you wear black socks and dress shoes to the beach?
That’s a good line. Shit! Fuck. I gotta do a rewrite. Maybe it’s because I’m the son of a caterer, or maybe because I’m old-fashioned, but it just drives me crazy. Inevitably, every fucking show I do, there’s a guy with big hairy toes in the front row, wearing these awful things. What makes you think that the entertainer wants to stare at your Frodo feet while he’s up there? By the same token, when a woman is in the front row and she has a short skirt on, it’s equally distracting, but not necessarily in a bad way.
When you roasted Jerry Lewis, you had Robert De Niro and Martin Scorsese on the dais, and after your killer line about Jerry’s Kids, you got “the De Niro Look”—that kind of half smile, half you’re-gonna-getwhacked-later look.
[Laughs] Well said.
It’s classic. What an honor.
Well, that’s the thing about being a comedian. The later you sleep, the more messages you have on your answering machine and on your e-mail when you wake up, and you just never know what it’s going to be. It’s an adventure. One day you’re face-to-face with the Goodfellas, and the next day you’re fucking with Shaq. Or Suge Knight. Then you’re in Israel at the West Bank, doing a benefit show for a settlement. And then a week later you might be in Columbus, Ohio, in a three-way with the staff of the club. It’s always a lot of fun. I can’t complain. I’m very lucky.
