Jeff Ross, AKA “The Roastmaster General” is a 25-year veteran who has done it all: He has performed on late night with Leno, Letterman, Kimmel, Fallon, and Ferguson. He has appeared in a number of films and TV shows, including his own show, The Burn with Jeff Ross. He has two recorded stand up specials, No Offense and Jeff Ross Roasts America. He is the author of I Only Roast the Ones I Love. He is heavily involved with the USO as he wrote and directed the documentary Patriot Act: A Jeffrey Ross Home Movie in which he starred in with Drew Carey. To top it off, he was the very first guest on the debut episode of the WTF podcast with Marc Maron, one of the top podcasts in the country.
Yet, that’s only half of it! Jeff Ross’s nickname comes from his blistering performances of high-profile celebrity roasts that have included Pamela Anderson, Joan Rivers, David Hasselhoff, Donald Trump, Bob Saget, Charlie Sheen, and James Franco—just to name a few! He is a staple of the New York Friar’s Club, and having been part of the last 11 Comedy Central roasts, he is easily one of the best insult comedians in the business.
But as mean as he may seem on stage, off stage Jeff Ross could not have been nicer. Beat with a bad flu, his voice was nearly gone, yet he still insisted to have the interview go on. Given his conditions, it was extremely kind of him to talk shop and share his comedic advice and wisdom with all of us. He performs at UP Comedy Club in Chicago tonight, tomorrow, and Saturday night.
Jeff Ross! It’s an honor, how are you today?
[coughs] I’m losing my voice, so I might be brief, but I’ll do the best I can.
Oh no! Okay let’s do this: You started in 1989, yet your first special didn’t come out until 2008. You took your time to get seasoned before you put anything out there. What advice do you have for comics who are in a hurry to make CDs, DVDs, etc. to get quicker exposure?
Well, you never feel like you’re taking your time, you feel like it’s just going slow. Dave Chappelle once said, “You only start out once.” So, you have to enjoy the process: Recording yourself, writing the jokes, trying them out on your friends and audiences. Enjoying that moment when you go from five minutes to ten minutes, and from ten minutes to thirty minutes, and then one day you’re a headliner. It just doesn’t happen after one night or one week.
And you have to enjoy bombing as much as killing. You can’t worry about putting out a CD when you’re not ready. Nobody wants to see an amateur CD! It’s not gonna help your career. It’s not going to propel you. Just do it for yourself. Get on stage every night for yourself.
You experienced tremendous tragedy early in your life, losing both of your parents when you were only 19. Do you think that was what pointed you in the direction of pursuing comedy?
Comedy wasn’t something I ever dreamed of or thought about. It was something that happened by accident, ‘cause I had nothing else to do. It was a way to meet girls, it was just a hobby, something fun. And I was good at it. I liked it right away. When somebody dies in your life… I mean, I lost my parents when I was just a teenager. You don’t ever think, “Oh, now I’m gonna be funny!” You think, “This is the worst! This is crushing!” So, I’m very lucky that I found that path.
[Loud, painful-sounding coughs]
Man, are you gonna be okay for your shows?
I don’t think so… I’m hurtin’ really bad. I got press all day tomorrow before my show, and I’ve lost my voice.
What do you do in a situation like that? Afterall, your voice is your instrument!
It’s never happened. Guess we’re gonna find out… [laughs]
You’re labeled as an “Insult Comic”. Since roasting is what you’re known for, do you feel like you’re stuck in that particular style?
Not at all. It’s only a small part of my show, I do whatever I want. People are there to see me, not necessarily any specific thing. In my show, I do music, I do regular stand up, I roast the audience and do speed roasting, and I also do poetry. I think it’s a journey. If any of your readers wanna get laid, have ‘em bring a date to my show ‘cause it’s gonna be very sexual. [laughs]
Your book is titled I Only Roast the Ones I Love: How to Bust Balls Without Burning Bridges. Have you ever completely burned a bridge because you went too far during a roast?
[laughs] I feel like if somebody gets mad and you actually do burn a bridge, you never hear from them again. They don’t really tell you because they don’t want to come off like they’re a bad sport. But as far as I can tell, I’ve been really lucky picking people that are good sports who can take it. And I’m really careful to pick people who are good, and who aren’t gonna get mad. But I also think that I’m really good at writing jokes that THEY can laugh at, too. You want people to leave the show going, “That was really fun!” Ya know? I don’t want to hurt people. I want to bring people together.
Who are some newer up-and-coming comedians that you enjoy?
Well, I’ve been doing this roast-style show in L.A. and we were doing it in New York at the New York Comedy Festival, which has been a breeding ground for the next generation of comics—especially roast-type comics. We had Sarah Tiana on last night and she was really great, she killed. I love Jesse Joyce, there’s so many…
There’s Monroe Martin out of New York, obviously Hannibal Buress out of Chicago who used to open for me there, and now he’s becoming a star. There’s a lot of really fun people coming up now, and I’m not really sure why or how that movement is happening. But, every time I turn my head I see somebody else that I love and laugh at. Brian Moses, Tony Hinchcliffe, Benji Aflalo—just so many funny new people coming out of the clubs of New York and L.A. and I’m sure I’ll find some new ones here in Chicago.
General advice & wisdom for younger comics?
You literally have to go the extra mile to get on stage. Stage time is prescious. Don’t squander it, and make the most of those opportunities. If you have a bad show, get right back on the next night and do it again—or even that night, if you can. Don’t let anything stop you. If you’re funny, you probably know it. Some people go into it because they just want to be famous. Those people usually don’t make it. People that are funny get famous as a byproduct of that. The funniest comedians are the ones that don’t even want to be famous, who can’t even handle that part of it. I think the funny people know who they are. And I think all the funniest people get that shot at the big time. So, stick with it.
You’ve done so many things in this industry, you’ve practically done it all. What happens when you get to such a point in your career? What else is there to do?
What happens is you start getting more and more opportunities, and you start working even harder than you did when you were a beginner. And that’s why I sound like this today. [laughs]
Do you think the passion is still there when comedians get to such an intense level like that?
Well, not for everybody. I feel like comedians either burn out and get a writing job, they OD, or…they go to 100. I mean, the greats: Henny Youngman, Bob Hope, George Burns—these guys were in their 90s! Some even make it to 100! Comedians are ageless. Rodney Dangerfield was in his 80s making movies for teenagers. Comedy is ageless.
What is the key to not burning out when you reach that higher level of hard work?
Learning to say “No” and not do everything. Like, when some open-miker wants to do an interview for half an hour for his website, maybe say, “No.” and don’t burn out your voice. [laughs]
[laughs] I got nothin’…
I gotta rest my voice. This has been AWESOME! But I’m hurtin’ today and I’m terrified about tomorrow.
No worries, it’s been an honor talking to you. Thank you for your time, hope you feel better, looking forward to your show!
Thanks for your questions brotha.
INTERVIEWED & WRITTEN BY David Gavri