SL’s Exclusive Interview – Joe DeRosa Wrote The Book On Cheating

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Comedian Joe DeRosa is veteran of the stand-up comedy scene. He is a regular on The Opie and Anthony Show on XM satellite radio and Fox News Channel’s Red Eye. Joe has also starred in his own special on Comedy Central and appeared on TV shows including Louie and Bored to Death. Joe recently teamed with his fellow stand-ups Bill Burr (recently seen on Breaking Bad) and Robert Kelly for a new book Cheat: A Man’s Guide to Infidelity – think of it as “Cheating for Dummies”. I caught up with Joe to talk about the book and the future of fidelity. Intelligent and edgy, this comedian takes his views on relationships quite seriously but definitely brings the funny in our though-provoking interview.

Socialite Life: So, what was the inspiration behind Cheat?
Joe De Rosa: Well, (Bill Burr, Robert Kelly and I) wrote and produced a short film called Cheat and it went to the Tribeca Film Festival and it was pretty well-received. We wanted to do something else together and someone said we should write a book based on the concept of the movie, about teaching someone how to cheat properly, because that’s what the movie was about – it was a comedy. It would be a funny book to write, so we thought yeah, that’s a good idea and it will help us cross-promote the movie a bit. So we did. That’s it, that’s all there was.

Much more from Joe DeRosa…

SL: How did you get together with Bill Burr and Bob Kelly to work on these projects?
Joe De Rosa: Bill and Bob have known each other forever because they started out in Boston as comics. I’ve actually known Bobby a little bit longer than I’ve known Bill. So, it was just one of those things – over the years, they had a lot of history together as comics and I became friends with them and we all became closer and all of that stuff. It just got to a point where we were all very close friends and I guess Bill was the one who said initially, “We should do something together. You get into this business to have fun and to do the stuff you love to do and to work with people you want to work with. Why are we waiting for someone to hand us a chance to work together? Let’s do something.” And that’s what caused us to make the movie – and then we ended up writing the book.

SL: Describe the book to me. Is it a compilation of stories about men who have cheated or more of a “how-to” book?
Joe De Rosa: It’s a how-to handbook, but sprinkled throughout the book are true cheater stories from friends of ours like Colin Quinn and Anthony (Cumia, from The Opie and Anthony Show) and Keith Robinson, Rich Vos – a lot of our friends gave us stories for the book. And those stories are in there because they’re true stories that we, as the authors, were able to comment on and – in a funny way – say, “Here’s what they did wrong, here’s what they did right, here’s why he got caught, etc.” But also too, each story ties into a chapter, like “Here’s what we were talking about in that chapter” and then the story kind of relates to that idea.

SL: There’s a lot of comedians involved with this book. Do you think that living the lifestyle of a stand-up comedian – with all of the touring and being away from home – skews your views on cheating?
Joe De Rosa: Hmm…I don’t know. I don’t think being on the road skews your perception of what actually goes on with this stuff. I think what traveling does – or can do – is sort of open up or expand your knowledge of how often this does go on – because you’re out there on the road and you’re meeting a lot of people – and especially in comedy, you’re meeting a lot of people in social and drunken circumstances a lot of the time. People are out, they’re having fun, they’re partying, whatever. You sort of start to get to see the behaviors of people when the cat’s away – so to speak – and I think also too people act a little more loose around comedians. They might tell you something that they’re up to or reveal something to you or act a little more freely in front of you because they don’t think they’re going to get judged by you. So, with that being said, I think traveling on the road does sort of let you peer into the world of fidelity versus infidelity and on a greater scale than most people get to who leave their house, go to work and then come home every day. But at the same time, I don’t think it skews your perception of cheating. I don’t think it gives you a false concept of how often it’s going on out there or how often it isn’t going on.

SL: The reception of the book has been great so far, but it’s probably inevitable that you’re going to get some criticism from women. What would you say to them?
Joe De Rosa: Well, we haven’t gotten a lot of criticism from women. There have been some very reputable women who have read this book – whose opinions we value very greatly – and who I think are the people that if we were going to be nailed to the wall for something, these would have been the people to do it. And because they were looking at it beyond the fact that it’s funny and it’s social commentary – which is what it’s supposed to be first and foremost. It’s a comedy book, it’s meant to be funny. But, you know, there were people who read this and we thought that somebody’s going to pose a good argument against the book or a criticism and it would probably be this person. And lo and behold, these people came back and said “We love it, we think it’s hilarious, we think it’s irreverent. It’s truthful. They felt it was very worthwhile and that sort of reinforced our premise that anybody with an open mind should enjoy this book. Anyone with an open mind should understand this book.

We can all sit around and say it’s wrong to cheat and people don’t do this and this is not the way it is. We can all pull our own legs but, I mean. come on. There are genetic and biological reasons as to why people have these urges and as to why people want to go and do these things. There are social stigmas that prevent us from talking about this subject in a very mature way, even if we are being funny about it, but it’s something we should talk about and that should be discussed. And people like to kid themselves. I think any honest person that reads this book, that’s got an open mind and is up for a laugh and wants to learn something would read this book and enjoy it. We call it “a man’s guide”, but it’s as much for women as it is for men – if for nothing else, it will teach women what kind of tricks men are up to. I really feel strongly about that.

I realize why there’s the potential for criticism, but I really don’t agree with it. I think that anybody who acts like they don’t have basic sexual urges is lying. I think people who act like they can’t understand why someone would want to occasionally have more than one sexual partner is lying. I say all of that under the umbrella of I’m not saying it’s okay, we’re not telling you to go cheat. We’re not saying go out there and do it. What we are saying is understand where this is coming from and if you’re going to do it anyway – because people are – you might as well do it right. And if you don’t do it right, you’re going to ruin lives. You’re not just going to ruin your life – forget about it from a selfish standpoint. You’re going to ruin the life of your wife, your girlfriend, potentially your children. There could be a lot of financial loss. There’s going to be a lot of turmoil and it’s not pretty when, at the end of the day, all you were trying to do was to satisfy some basic human sexual urge one time. But people don’t understand these urges because, again, they’re not discussed in a mature fashion. There’s no open discussion about this stuff – which is shocking with all of the sex you see on television and film and whatever. It’s shocking how stunted our understanding of this stuff really is. When people don’t really have a grasp on a lot of these urges and they don’t get where they’re coming from all of the time and then they go out and make decisions because of impulsive passion and they hurt people because of it. They ruin people and it causes a lot of damage. So that’s really the basic premise as far as justifying the argument for this book. It’s like, two things – it’s supposed to be funny, it’s a goof, have fun with it, but, number two, we’re not telling you to do it, we’re telling you how to do it because if you’re going to do it, do it right.

SL: With this book and sites like Ashley Madison almost promoting infidelity, do you think monogamy is dead – or at least on the endangered list?
Joe De Rosa: Look, I don’t think monogamy is dead, and I don’t think it’s endangered in the sense that it’s going to go away. But I do think that monogamy is a concept that has been sold to us that we are not supposed to question. And, just as a culture progresses and people start to ask more questions about things concerning government or religion, or whatever – these sort of social institutions that are just fed to you from birth you’re supposed to believe in this thing. And the older you get, you’re like “Wait a second, this kind of doesn’t make sense to me though…”I think monogamy is another one of these institutions in that is slowly becoming more questioned and argued. But I don’t think it’s going to go away. I don’t think it should go away. It can be a very beautiful thing. I mean, look, we’re all believers in it. We talk in the book about we’re bank robbers that got caught and have been in jail and now we’re telling you how to rob a bank. We’re not out there still robbing banks. We went through this stuff, we had the experiences and now we’re speaking from experience but it’s all behind us now and we think that a lot of guys can put it behind them when they understand it and when they understand what it is and how to deal with it, how to handle it.

So, no, I don’t think monogamy is dead and I don’t think it should die. But I do think that people should be allowed to live a life of being single and dating multiple people and living a more openly romantic and sexual lifestyle – if they want to. That is still very condemned and that’s another thing that’s addressed in the book. There’s a whole chapter on sex and the single man and how just because you’re single doesn’t mean you’re not cheating – and that’s a real thing. You’re not supposed to cheat when you have a girlfriend, you’re not supposed to date multiple people when you’re married, but you’re also – for some reason – not supposed to date multiple people when you’re just dating. You still have to play all of these games of well, this girl was here on Tuesday, so when this other girl comes over on Wednesday, I have to make it look like the girl from Tuesday never existed or else it’s going to be this shit storm and I’m going to be called an egomaniac or a pimp and whatever. And it’s ridiculous. When are you supposed to go out there and have a healthy sampling – and I don’t mean I mean healthy like you’ve got to f–k tons of people, I’m just saying healthy in the mental sense – experiencing of different people and experiencing different romantic and intimate and sexual situations – the way any grown person should be able to do, actually.

It’s interesting. You see a lot of marriages fail because people get married right out of high school or college and you see these marriages start to break up when they’re in their 30s, people hit a certain age and it’s not working. I see other people get to a certain age who weren’t married and sort of tap out and say, “I guess it’s time I do this.” Or they ask themselves, “Am I just going to be single forever?” or “When am I going to settle down finally?” You hear people dealing with monogamy like it’s a freaking ultimatum of some sort. I think that’s sad. I think if you’re going to be monogamous, it can be extremely beautiful and wonderful but you also have to understand what it means. You don’t just do it to do it. There are social pressures that push people into that lifestyle when they don’t want to go into it necessarily because they feel like if they don’t, they’re going to be an outsider. I think that sucks and I think you should be able to live life as a single person if that’s what you want to do.

SL: I know you’re touring behind the book and the movie. Where are you headed – and where can people see the movie?
Joe De Rosa: The movie’s online, it’s at, so you can see that there. And there will be hopefully different events and things where we can push the book and get to meet the people and all that stuff. You can get the book now on the web and buy the book, download it, buy it at Barnes and Noble and it’s out there.

SL: What’s next for you?
Joe De Rosa: I have 2 different web series coming out that I created, directed, wrote and starred in. One’s called “What Are We Waiting For?” new episodes are coming up this month on The Warner or They should be debuting October 23rd. It’s a really funny show. Bill Burr’s in an episode, Jim Norton’s in an episode, Opie’s in an episode, Anthony Cumia’s in an episode – we’re really excited about it. I have another web series with Nikki Glaser called “We Should Break Up” that’s going to be on That one will be out sometime I think in late October or early November.

Cheat: A Man’s Guide to Infidelity is available in bookstores everywhere. You can keep up-to-date on Joe’s tour dates and other projects by following him on Twitter @joederosacomedy.