Busting the balls of the people you love isn’t an easy gig. But comedian Jeffrey Ross—who is best known for doling out brutal insults to friends and foes alike on the annual Comedy Central Roast specials in addition to his duties as Roastmaster General at The New York Friars’ Club—has made a living out of it. Outside of his stand-up career, Ross also directed Patriot Act: A Jeffrey Ross Home Movie, a documentary about his experience performing for U.S. soldiers stationed in Iraq. Ross (who appears Friday, July 31, and Saturday, Aug. 1, at Comedy Works) spoke with The A.V. Club about fending off Penny Marshall, roasting his former idol, and “The Three ‘F’s” of effective ball-busting.
The A.V. Club: Out of all the people you have roasted, who has been the best sport?
Jeffrey Ross: Everyone I’ve roasted has been a great sport. The only person that ever came after me was Penny Marshall. It all started when I roasted her ex-husband Rob Reiner. I said, “What was your wedding song, ‘How Much Is That Doggie In The Window?’” I saw her at a roast two months later and she attacked me. Luckily I’m a black belt in karate.
AVC: How did she attack you?
JR: She headed toward me in a drunken rage. So, I made a joke. I said, “Which one were you again? Lenny or Squiggy?” Of course, they escorted me out the back door. Occasionally a roastmaster needs to get out of Dodge.
AVC: What was the most difficult part about filming Patriot Act in Iraq?
JR: There was just so little downtime. We could only sleep, like, four hours a night when we weren’t interviewing soldiers. So, I would say that the hardest part was keeping my eyes open. However, it was very gratifying.
AVC: Your documentary has also won some awards. So now that you are an award-winning director, do you have plans to make any other films?
JR: I’m working on a couple right now. I don’t know where they will lead. Right now I’m working on a book, that’s my next project.
AVC: What kind of book?
JR: It’s called I Only Roast The Ones I Love: How To Bust Balls Without Burning Bridges. It’s a long story, but Howard Stern suggested that I write a book about how to bust balls.
AVC: What are three tips for effective ball busting?
JR: I always use “The Five ‘F’s.” One of them is “fast.” Whatever you say, you have to say it fast. Also throw in a “fuck” every now and then. Then there’s “friendly.” You want to start with a compliment, like “Yo Stevie, you’re a great guy, but your breath smells like anchovies.” I can’t remember the other ‘F’s right now.
AVC: Okay, so it’s “The Three ‘F’s.”
JR: Yeah, “The Three ‘F’s” for now.
AVC: You mention in your act that you are from New Jersey. What state deserves more ridicule than the Garden State?
JR: I think Jersey has a good reputation. Between Springsteen, The Sopranos, and Sinatra, we have a lot of swagger. I feel like everybody in New Jersey is an insult comic at heart. We just love to bust each other’s balls. I think Jersey stands alone, and because I’m from Jersey, I never make fun of where people are from. I’ll make fun of what they look like, but I’ll never make fun of where they are from. Jersey is special.
AVC: You divide your time between New York and Los Angeles. Where do you stand on the New York vs. L.A. rivalry?
JR: New York wins hands down. I always say that I write the jokes in New York and I sell them in L.A. I’m an East Coaster. I went to see Springsteen in L.A. and it felt like I was channeling my inner East Coast Jersey upbringing.
AVC: What was scarier, filming your documentary in Iraq or sharing the dais with a visibly intoxicated Courtney Love for Pamela Anderson’s Comedy Central roast?
JR: Well, the Iraq trip was scarier, but ultimately, I’d have to say that Courtney Love is more dangerous than any terrorist I’ve ever met. After the roast I’ve never run into her, but by all accounts, I saved her life.
AVC: Oh, really?
JR: The next day she went into rehab. A lot of people say that I roasted her into sobriety.
AVC: When you watch the special, it seems like she didn’t get the concept of a roast. But in her state, she also didn’t seem aware of a lot of things…
JR: I think she loved it. If you look at the pictures that came out afterwards, she’s got her head in my lap like five minutes after I roasted her. I’m a big fan of Courtney Love. I love Hole and I love her acting and I love her attitude. I just hope I never meet her in a dark alley.
AVC: You’ve mentioned in previous interviews that Gene Simmons was your favorite celebrity to roast. Why is that?
JR: Oh, because it could have been a three-part mini-series. Look at the guy. I grew up worshipping Kiss. I was in the Kiss Army. He was my favorite member of my favorite band. I totally worshipped and idolized him, until I actually met him when he ruined all that.
AVC: Who would you like to roast that you haven’t gotten the chance to yet?
JR: The Onion. Now there’s a newspaper so bad R. Kelly wouldn’t pee on it.
AVC: We put together a list of celebrities that we would like you to roast off the cuff.
JR: Okay, I’ll try.
AVC: Spencer Pratt.
JR: Spencer Pratt? Is that the guy from The Hills?
AVC: Or you can roast the whole cast of The Hills. That works, too.
JR: Oh boy, I’d rather bang the cast of The View. Seriously, though, Spencer Pratt? That guy is adorable. He’s like Lance Bass’ retarded nephew.
AVC: Miley Cyrus.
JR: Well, I’ve got a good story about Miley Cyrus. My nephews begged me to take them to see Hannah Montana, but it was sold out. So I took them to see Hannah New Jersey.
AVC: How old are your nephews?
JR: They are 6 and 12. They got a couple handjobs in the lobby on the way out.
AVC: Okay, here’s one for you to roast—Lindsay Lohan.
JR: You know what? Lindsay is a friend of mine. I feel like she’s gotten a raw deal. So, Lindsay, wherever you are, I hope you find love, and, uh, I hope I can watch.
AVC: Amy Winehouse.
JR: Oh my God, she is the greatest. She makes Courtney Love look like Mother Theresa.
AVC: Paris Hilton.
JR: The Hilton sisters. How great is it that two sluts are named after a cheap motel?
AVC: Oprah Winfrey.
JR: Oprah. You don’t mess with Oprah. She has enough money in her left pocket to have me killed.