Just for Laughs - Jeff Ross Roasts Chicago - Interview & Review

If you've watched Comedy Central a couple times over the past decade or have ever seen an infamous Comedy Central Roast, then you're familar with comedian Jeff Ross. Jeff, also known as the Roastmaster General, was in Chicago this weekend to Roast Chicago as part of TBS' Just for Laughs comedy festival for the second year in a row.

I got to sit down and talk with Jeff about how nervous he was his first couple roasts, his favorite roast joke, remembering Greg Giraldo, and much more. Following the interview I have a review and exclusive photos from Friday's show that inlcluded several big surprise guests.  

Being a comic and performing in front of a crowd is nerve-racking enough, but I imagine doing a roast is even more intense because you don't want to show any signs of weakness or nervousness. Can you tell us what it was like doing your first couple of roasts?

I was nervous. Once you get your first laugh, the nerves leave the front of your head and go to the back of your head because you know you have something. If you have good jokes you're always less nervous. If you're prepared, you're not nervous. And if you get there early I feel like you get less nervous. So those are tips... to be prepared and get there early, get a feel for the room. I was sh*tting my pants those first couple roasts.

What do you remember most from one of the early ones?

I just remember Milton Berle and Buddy Hackett heckling each other in the middle of my first roast. So I became an innocent bystander while these two legends battled it out. Like two dinosaurs killing eachother off.

Which roast was that?

For Steven Seagal. My opening joke was, "A lot of you don't know me, but I feel uniquely qualified to be here today because I'm also a sh*tty actor." Then I knew I was funny and could take whatever they threw at me after that.

You talked about being prepared with jokes. Is that what you tackled right away and took seriously at the beginning... the joke writing?

Yeah, I always did that. I was always a writer first. Without the jokes there's really nothing to give the people. To say I'm here because I'm a good entertainer or my personality is so entertaining is nonsense, that's what puts the jokes over. So to me, the material is the foundation for everything I do. Even today (Friday 6/15), for my shows tonight, I'll spend five minutes on my appearance and three hours on the material.

Not only are your roast jokes incredibly memorable, but you have some of the best ad-libs to people's reactions of the jokes. Do you prepare some of those ahead of time?

Oh yeah, you always have to have one or two that's in the margin and you might get to say it or you might not. But also, if you know your room and know who's there, the improvs will come a little easier. I feel like you want to experience everything that the audience is experiencing. The moments, playing the moments.

Do you have a favorite roast joke you've done?

I had a pretty good one recently for Betty White that I like. It got quoted a lot and when people quote a joke I get excited. I said, "Betty White is so old, the color white is named after her." You've heard a lot of Betty White jokes, but that's an original take.

One of yours I remember was, "I wouldn't f**k Bea Arthur's d*ck with Andy Dick's p**sy.

Which is almost like a joke on a joke, but at that point, you reinvent your own stuff once they get quoted enough. So I like that one, yeah. And the reactions make it priceless, Bea Arthur would always make an okay joke into a great joke just by the face she would make. So the room would explode when they'd see her get mad or feign being mad.

Lastly, you come from the Tough Crowd group, the Cellar group... can you talk about what it was like to know Greg Giraldo as a comic and as a person?

Well, you knew right away when you met him that he was still an open micer. He was still a part-time lawyer when I met him, but you knew right away he was very special, that he was a guy you were going to know. If you were going to stay in the business, you were gonna know that guy. And when somebody makes an impact like that right away, you don't forget it. I remember he was even my lawyer at that point. He had done a legal odd job for me as a favor, so I knew him as a lawyer really before I even knew him as a comic, interestingly enough. He was always very bright. I remember him sort of dancing circles around a local judge on Long Island to get me off a bullsh*t charge, so I'll owe him forever. I would have been in jail right now if it wasn't for Greg Giraldo. *

Last year, Jeff's show was one of the most talked about in the festival and it should be again this year.

Friday night at Park West in Lincoln Park, the show started with a crowd-pleasing surprise as Sarah Silverman was one of the opening acts who performed then introduced Ross.

Jeff began by roasting celebrities and telling such memorable jokes as, "For years I thought Tupac Shakur was a Jewish holiday." Soon after, Ross brought out Chicago native Jeff Garlin (Larry's agent on Curb Your Enthusiasm) to drum to the punchlines of Ross' Chicago Roast jokes. Ross's ultra-specific and hard-hitting jokes for the Roast of Chicago were possibly the best part of the show. My favorites included, "Chicago is the third best city in the country, it's the Chloe Kardashian of the US," and "Chicago is the best city in the Midwest, which is like being the prettiest girl in fat camp."

Jeff then allowed fifteen volunteers from the audience to come onstage, and called Sarah Silverman back to aid in roasting every now and then, although Ross did most of the heavy lifting. Most of the slightly to very drunk audience members soon realized what a poor decision they had made.

As hard as the audience laughed at Jeff roasting these people, we couldn't help but feel embarrassed for them as they were ripped apart during their improvised individual roasts. Ross would ask the willing prey questions first to quickly gather material. "What do you do?" "I'm a salesman." "What do you sell? Not personality."

The audience felt most embarrassed for a girl who somewhat resembled Drew Barrymore, but whose clothes were way to small for her. "It's Susan Boyle's granddaughter." "Drew Barryless."

Jeff closed the show by asking anyone to come up who can play the keyboard. Soon after a music teacher came up and accompanied Jeff as he read some very funny love poems he had written. Jeff's spur of the moment chemistry with the music teacher was both charming and funny.

Because of the surprises, overall hilarity, Chicago specific references, and the variety, this show is a must see if it comes back next year.


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  • Great interview, Scott! Great get with Ross and I liked the questions you asked too. Keep up the great work.

  • I liked his off-white joke.

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