GregfitzIn his new memoir, "Dear Mrs. Fitzsimmons," comedian Greg Fitzsimmons creates a self-portrait of the comedian as a young man, complete with photos and letters upon letters from disciplinary figures in his life to illustrate just how Greg evolved into the stand-up comedian, TV comedy writer, and radio/podcast broadcaster you know today.

You can listen to an excerpt from Fitzsimmons himself, courtesy of Vanity Fair. And if you buy it as an e-Book, you'll get to see/hear his famous friends read the letters.

Last week, Fitzsimmons performed stand-up on Late Show with David Letterman.


  

Also last week, Fitzsimmons sat down with The Comic's Comic to talk about his book and more in a wide-ranging discussion.

How did the Fitzdog Radio podcast evolve out of your Sirius show on Howard 101?

"The podcast was born out of feeling like there was more meat on the bone at the end of the Sirius interviews. So my producer, who just happened to be a guy who knew a lot about podcasting, because he worked on, or still works on Adam Carolla's podcasts. So we basically do the Sirius interview. We stop down for about maybe five minutes, and then we just start recording it for the podcast. So that's Monday. And then the second podcast each week, I'll go, I'm going to Seattle tomorrow morning, so I'll do a podcast from Seattle. And I'll interview maybe the comedians on the show with me, I'll talk about Seattle. Just kind of do my own little rant about what's going on that week. And then, if I'm in L.A., sometimes I'll line up another guest. But, you know, people really seem to like when I do it alone sometimes, because, when you have a guest, you have to service that guest. You have to introduce them. You don't really have control of the podcast as much, and that can be a good thing, but I think once in a while, it's nice to answer a lot of the mail I get through Twitter. And we have a couple of games that I like to play through Twitter. Overheard. And Half a Man. I catch up on stuff, and I get really good feedback from it, so it's been a labor of love. It certainly hasn't been for money. And I'm hoping that the goodwill of getting a free podcast will translate into, 'Hey, go buy the book now!' I'll see if that pans out or not.

So far, we're looking good. We're on our third order of the book in pre-sales, but a lot of that is based on the bookstores knowing what media that I've got. I've got Letterman coming out Friday, and I did Stern. Kimmel and Chelsea Handler. And then just millions of radio interviews. Bob and Tom, I've been doing every week. The exposure's there, but it's a very crowded marketplace right now. I'm sure you know. Carolla. Baba-Booey. Jim Breuer. Mike Birbiglia. So I mostly believe that we'll all find our own audience, and we're not necessarily pulling from each other's too much, but my two main platforms are Stern and Carolla. So obviously I'm not getting the attention I would be getting at another time. But I'm looking at it like, look, this is a book I'm proud of. This is a good book. I think it's a little more of a literary read than the average comedian book would be, and I hope it gets reviewed and talked about, maybe over a longer time will do the business that Baba-Booey's doing out of the gate. He's just on fire. And I'm not feeling competitive with him. I'm just trying to have more of an awareness of what to expect on my end."

This is such a fertile time period for comedians, not just books, but also podcasts, CDs and DVDs. It feels like there's so much more out there to review and sift through than there was three years ago.

"Yeah, I think comedians are lazy. We tend to catch up a little late, and while bands were doing all of this stuff, we were just doing live shows and selling crappy CDs on our own. I think Comedy Central stepped up and started making more deals for CDs, and then a lot of indie rock labels started doing comedy CDs, and then obviously now, DVDs. Although DVDs do not sell as well as CDs, at all. I think there's something that maybe people are used to listening to it. And now, there's a higher quality of stuff going out now from bigger name comedians, and I think that they're not seen so much as like, what would have been, 'You know you're a redneck when,' I mean that kind of genre comedy book, doesn't exist as much anymore. And now you're getting comedians that essentially take essays and beef them up a little bit, and they're not necessarily connected. Or, like Gary, Gary Baba-Booey, he went deep and did a real memoir."

Athough his is probably unlike yours, in that yours really reveals the makings of a stand-up comedian. Did you feel any worries about giving away company secrets? This is how someone becomes a comic.

"I don't think anybody has the same path as another comic. You look at Dave Attell. The guy didn't have a drink or a cigarette until he was already pretty successful, and people associate him with this wild renegade. You know, Louis CK started out making short films. I know comics that started out as street performers. Guys who were out on the street telling jokes. Rick Aviles. They ended up becoming big comedians. So when comedians come up to me and ask me for advice, I just don't know what to tell them, really. I just say, if anything I say: 'Don't do it. If there's anything else possibly you could do with your life, do that. Because you're going to miss your cousin's wedding. You're going to lose a lot of girlfriends. And you're closeness with your friends is going to get thinned out. You'll have. I mean, I've been very lucky career-wise, and part of it is just I was born white, middle-class, dad paid for college, male, not bad-looking. I'm not good-looking, but I'm not bad-looking. So I had a pretty good set of tools to go into anything, really. I think I have the perspective that this country is so fortunate. Anybody, the poorest person in this country could line up with the better half of many countries in the world, and then, on top of that, I feel almost like a guilt, that I have been put into this category of white male, not poor, and you know, from a family that, as you read, was fucked up, but also had a tremendous amount of loyalty and support and laughter. So I've been fortunate in my career. Literally, I think I've made more money every single year for 20 years, with very few exceptions. I had one or two years where it really spiked because I was on a hit show, writing, or producing, but in general, it's been something that I feel like I tell comedians, 'Don't go in it for the money, because you won't make it at first.' I didn't make money for the first seven or eight years. Truly starving artist. Really fucking broke. But then once it kicked in, comedians who are responsible enough to show up for work and not get too drunk, people count on you, they keep coming to you for work. It takes a long time to get to that point, but then it just happens. It just happens.

I remember watching it happen to Jim Gaffigan. I remember watching it happen to Greg Giraldo. And you know, you're all of a sudden, going from scrapping, to getting a five-minute free spot in the second story of a restaurant in front of nine people, taking subways to Brooklyn for a show, and then all of a sudden, you've got a Town Car picking you up to take you to a TV taping. And it just, bam! And once that happens, if you've got your shit together, you can stay there."

You also had the benefit of starting your professional career in the Boston scene, which was and is a very lively and vibrant scene for comedy.


"Yes! Other than San Francisco, there was not another place. Maybe Houston. But Boston more than anyplace in the world. The best thing about it was that it was a sealed community. Very few comics came in from the road and worked Boston because there were so many good comics, so it forced you to not only have material that was different from anybody else, you had to have a persona that was different. 'Hey, you're doing Kevin Meaney! Or you're doing Don Gavin! Get your own fucking voice.' So it became a place that I think was, there were a lot of gigs, there was a lot of work, there was a lot of support, and you watched guys that, to this day, I feel are better than any comic I've ever seen. Don Gavin, I'd put up against anybody."

And those guys, Gavin and Kenny Rogerson, they're still working,

"Still there. The Viper. Steve Sweeney, Mike Donovan. You know, Nick DiPaolo came out of that fold. You look at Nick DiPaolo. There's not a guy who can hammer a crowd as much as Nick can. And that's what these guys in Boston are doing, but nobody knows about it."

What do you think it was about your crop that managed to break out nationally, whereas the older guys are Boston and New England-centric?

"I left because the second I started headlining, I left Boston. That was sort of a plan that I had. I didn't want to be a big fish in a small pond. I watched guys who leaved town like Louis CK and Nick DiPaolo, and I saw that there was a track. Joe Rogan, who was a good buddy of mine coming up. And I saw that they were going to New York. And they were coming back and forth. I saw that just by becoming a player in New York, your stock rose in Boston. You had more credibility. You could earn more money. And you could come up and make enough money that you could afford to live in New York. So you know, I think the guys that stayed had been there from the beginning, the Ding Ho days, they are legends, but I don't think they made a mistake. Those guys made a ton of dough. Cash. They still do. They live where they want, around their family, around their friends, their audience knows them, they know their audience, it's a great life. Every time you travel and try to go to another level, there's a risk that you won't make it, and you have to cut yourself off from the world and the life that you knew before and was comfortable. 

"So one of the things sometimes I struggle with is having left New York. Last night I was at this book party, all of my relatives were there, and when I walk down the street in New York City, I feel like I'm in my bathrobe. This is where I live. This is my comfort zone. This is where I write, this is where I'm creative, this is where I talk to people. I feel like from the cold weather, to the quickness with which people answer you, the sharpness, and I look at maybe moving to L.A., that that was a mistake. I don't know. I think I gave up a lot to do that. My wife is from Manhattan. My kids would have done well to be around their cousins. It's something I think about coming back to. In other words, the short answer: Everybody has to decide what's going to make them happiest. If you want to be the star, or you need to make millions of dollars, go do it. But just make sure that you know why you're doing it. And I feel like I've had a great experience in L.A. I got a lot done, I learned a lot, but I feel like the homing instinct's kicking in. Every time I'm here I'm just like, as a comedian, there's no other place where you can grow and develop like you can here."

It forces you to.

"I did a show last night after the party and I asked Jim Breuer and Dave Attell to come down and be on it. And you know, Breuer goes up, and he drove up from New Jersey for a 15-minute spot on my show for no money. His shirt is pressed, his hair is all done, he's looking at notes, goes up, just destroys, gives it 1,000 percent. Guys don't do that in L.A. Dave Attell goes up, he's got 10 minutes on the Chilean miners, he's got 10 minutes on a story that just happened two days ago. There's a black guy in the crowd. It's my show, so Attell goes, 'Look at that one black guy in the crowd. Fitzsimmons, you've got one black fan. Which is one more than Sinbad has.' He's just…and you can't get that sharp unless you're in the gym every day, and unless you're in front of New York crowds. You know. They're demanding. But if you get 'em, they're smart, they're diverse, and it's really, L.A., you've got a bunch of white people who are waiting for Jerry Seinfeld to walk in. And he ain't."

No, he's not. He'll walk in here. When you went through all of the letters for the book, did you find that it brought a new sense of clarity to your life and career arc?

"Not to my career, but to my life. I rarely even use the word career because I feel like it sounds so calculated, and my career has been just a drunken knife-fight in an alley. Who's coming at me? What do I need to do? Throw myself into situations, whether it's writing or hosting or auditions or going on the road. I go out of fear. So the book informed how I got that energy, but there's nothing I can do to change that. That's rebelliousness to me, is just throwing yourself in the middle and reacting to that, to not having a plan. And I realize now, if anything, I need to accept that. I've been trying so hard to pick, if I could just stay on a show. I go on these TV shows and I write on them, and then I leave. I don't like them anymore. And then I go back on the road, and then I get so lonely after a while that I go, I have to get back on a show. And I do my radio show and my podcast, sometimes I have so many things that my head is spinning. I have to got to pick one thing. The book made me realize: That's never going to happen. I've just got to come to terms with this is my life. I've got ADHD and I'm Irish. One career won't do it."

You're just going to lash out at whatever's there.

"Every situation is a challenge to me. The book is about authority, and this compulsion to fight it, push it back and tell it you can't tell me what to do. It goes back to Ireland. You see it with occupation. You see it with Jews. That's why Jews are comedians also. There's a dynamic with the audience that's very related to, it's a power structure. Who's in charge. I think with Hollywood, I maybe didn't do as well out there, in terms of acting, as I could have, because I give off a real attitude that you're not going to tell me what to do. And Hollywood says 'No, we're not going to hire you. Our job is to tell you what to do. We direct you. We write your words. We edit you. We tell you when to go to the set.' And all of that stuff, as a comedian, is a very hard transition to make."

So what do you think of the deal that Louis CK has been able to carve out for himself at FX, and have essentially complete control over his show?

"I think Louis fucked everybody. He brought in a show that's so good, on such an incredibly low budget, that the bar has been set. Once somebody does that, the industry says — because they all know how much is being spent on the show."

And he says publicly how much.

"I heard it was $150,000 per show. What did you hear?"

He said publicly $300,000.

"If it's 300, that's about a third of what most shows that are scripted come in at. So it's so successful, they ordered a second season after two or three episodes, it's got buzz, it's got critical acclaim, it's got numbers, he's bringing in big names, Ricky Gervais, and it's because, like I said, he started out doing short films. This show is essentially three short films. It's three acts. They're not necessarily that strongly related. It's snapshots of his life. And he's able to write it, act in it, direct and produce it. But his strongest asset to me is his casting. I mean he brings in such unusual people, with odd faces, that he seems to not direct. They're so organic seeming. I almost think he finds them and then writes around them. Doesn't it seem like that? Like there's no way an actor could be that good. And in every episode there's somebody staring at him in a supermarket with a look on their face, like they're a character in a Fellini film, they're four-dimensional, and they're like telling usually. He deals with isolation a lot. He picks characters who have absolutely no emotional energy, and it brings you in, because nobody else does that. And to call in favors for people to do it on the cheap and to be able to edit it, and have the energy to do all of that, nobody will be able to do what he did."

And hardly any other stand-ups have that background that he had, in terms of making the short films, which he was doing back in the early 90s.

"Maybe Albert Brooks."

But I'm talking about stand-ups working today who would be wanting their own TV show.

"I think that David Cross and Bob Odenkirk always to have that opportunity, but they seem to not be able to get out of being cool. They seem too much to want to please the other comedians. They're both brilliant. They're both hilarious. Obviously, "Mr. Show" is one of the best shows that's ever been done. But Louis doesn't care what other comedians think, and he doesn't try to be cool. He has a disgusting looking body, that he will show it all the time for laughs. He talks about aging in a way that most comics wouldn't do. In a business where you're supposed to stay young, he's really talking about getting old, and getting away with it. Louis is a guy that, you can't ever look at Louis and say, 'I'll do what he did.' From day one. I remember when he was 19 years old and he was headlining, he was driving me to a gig on the Cape in this old Mustang. He had this Mustang. He was a renegade from the beginning. He always did it his way. And it almost always worked. I tell people again and again, don't use him as an example. Or Attell. They're special machines. And Louis fucked us all. And you can put that in the god-damned article. When I talked about wanting to get off the road, Louis got me my first job writing. I told him how bad it was getting on the road, and he brought me onto Cedric the Entertainer Presents. It was a sketch show on FOX. They needed someone to write the monologues with Cedric, so I came in and did that. I worked with him then on one pilot that didn't go, and he brought me onto Lucky Louie. He's done more for me than almost anyone in this business, because being associated with him gives you credibility. What you learn from how he writes and how he understands the structure of things, I hope to spend more time with him, because it's been hard lately. I call and we missed each other, we tried to hook up in whatever horrible city we were in. It's hard when your friends get successful, you kind of have to kiss them goodbye."

Right, it's not as if there's a Boston comedy scene class of 1990 reunion.

"No, and you know, I'll see him, but the only time I'll see him will probably be when we're working together. The guy's on the road constantly. I've had friends get famous, and we're still friends, and I know they're not hanging out with other friends more, they're working too much."

And since you yourself can't focus on one thing, you're always going to be busy.

"It's something I'm very focused on though, is trying to find more balance. Having a wife and kids gives you opportunity to have balance, if you engage it. And I have. I've been very involved with my kids and my wife. Very in love with my wife, which is hurting my comedy a lot. I mean I literally go onstage and talk about how beautiful my wife is and how much we're in love, after 11 years, and it's killing me. I need to start fucking up. If she could blow the mailman, that would give me a little spike. If you're listening honey, green light!"

At least get a new seven minutes.

"I could get a new Letterman set out of it. So, yeah, my friends are important to me. All of my friends came out, kids I grew up with in New York, my buddies from college, all of my relatives, some comics that I'm friends with, and that feeling, when you feel it, reminds you that this is the best feeling. I did Letterman Monday night, and I felt like I could not have done better, and I'd worked hard on the set. And it was a real high, real rush, and I remember thinking, I want to do this more. But it can't come close to when you're around people you're connected to and close to, and not talking about the business. It's just, you feel the tank filling up. So I'm working on reconnecting. This book has been a bear. I've been out of touch for the past year, and now I'm really, I need some time back."

I'd suppose podcasting is intimate, but it's still distant. The audience is connecting to you, but they're not in the room with you.

"That part can be painful sometimes. The hardest part is, 'Welcome to Fitzdog Radio.' I mean, you're alone in a hotel room. And so I just start pacing and try to forget I'm holding a microphone in my hand, and then once I get going, it's like, Bill Burr's got a great podcast, and he just ramps it up and rambles and it's great. The worst thing you can do is script it out too much. You've got to let it fly. But when I have a guest on the podcast, it is that feeling I get with good friends, because a lot of times, they are good friends. Zach Galifianakis had come on, and we've known each other for 15 years, and how often do I get to sit alone for an hour — for two hours, if we're doing the Sirius show — two hours of uninterrupted, deep conversation with a friend? That's a huge upside to it for me. And guys have come in that I've gotten to know well, like Kevin Nealon has come in like three or four times. Or people you go like, I don't think I've met anybody as nice as that person, like Brian Regan. You walk away going, that's the best person in the world. Forget funny. He's just a good, good guy."

And he lives in Vegas.

"With a family. Talk about having balance. You know his schedule? Tuesday he gets up the crack of dawn. He does radio interviews for the cities that he's got coming up over the next few weeks. Then every other weekend, he works Thursday, Friday, Saturday in theaters. Sometimes three different cities. And that's it. So out of 14 days, he's on the road for three of them, and and he's on the phone for two of them. The rest of them, he's with his family, because he can do that. He's packing the theaters. But he didn't feel like he had to stay in L.A. and get that sitcom, or go to that next level. He loves his wife, loves his kids, wants to enjoy his life. Decided this is the level he's comfortable at. And that level is growing. He's done 22 Letterman and his audience has grown steadily, but it's his audience, its the audience he wants. And there's no when this happens, or if this happens. No, it's Tuesday, I get on the phone; Thursday, I get on the plane. I love it."

Seeing so many other comedians launch podcasts in the past year, has that made you react to how you do your show, or do you block all of that out?

"I used to be a fiercely competitive stand-up comic. As most guys who are out of Boston or New York were, but you just get to a certain level and you start realizing that no, it's my dreams versus my laziness. Those are the only two players. The more energy I put into my podcast, the more followers I get, the more advertisers I get, and the more comics who do podcasts, the more the advertisers are going to see it as a business model. They'll see this isn't just a couple of geeks talking about new software. We have an opportunity to take people who already have a fan base they've captured listeners for an hour. They're not passive. They're active. They're downloading every single hour, and if you place an ad in there, it's a live-read. This is what Howard Stern developed, because he couldn't get advertisers. He did live reads just to give the buyers something extra. So with the podcast, not only do you get a live read, not only do you get a captive audience, you can embed a link on our website. It's going to be something that I think is going to take off. There was an initial podcast bump seven, eight years ago. But it was seen as not connecting enough. In the past couple of years, though, I've been doing mine for I don't know, a year and three months, and yeah, I've seen a lot of other ones come up. It's funny how they're almost all people that I really like. Like Marc Maron and Chris Hardwick and Bill Burr and Jimmy Pardo. Carolla. Of all the ones in the top 20, they're all ones I've had on my show and I go on their show and I think it's, there's starting to be a lot of talk from production companies and networks, saying, 'Hey, we're going to create a network. We're going to bring on your podcast.' It's like, 'No, motherfucker. I've got a podcast. You want to come on mine? Buy some advertising time.' They always discover something and try to wrap their hands around it and give you a tenth of the money you were making before. And this is the Wild West right now. You've discovered gold! We haven't found it yet but we're onto something and I can tell from the fans that come out, there's a deep connection. They're not going anywhere."

I've seen that firsthand with Maron. He would come into New York and one show I saw, he sold 40 tickets. And then WTF got rolling and he sells out the room every time.

"I don't know that Marc does anything else except the podcast. He has really gone all-in. This goes back to what I said about getting back what you put in, he's really getting a lot out of it, and I think he's smart. There's a lot of people that offer come on and offer to do stuff for free. I have an intern. I actually have a producer that I pay a lot because he's very good. And I have to do very little. I turn on my recorder, I talk, I hit stop, I plug it into my computer and I email it to him and I'm done. I mean, I'll listen to it and give him some time codes, some cuts. Who knows, that might not be very much, that might be an hour of work for him. But I don't give a shit. I pay him well, and I want this thing to be quality. I don't want to disappoint listeners. I want them to feel like every time they listen, I've put some thought into it, I've tried to get a good guest. If I haven't, there's compelling stories or observations in there, and it's always honest."

You talk about your dreams vs. your laziness. Technology has really upended all of comedy in that way. Even 10 years ago, the Internet was big but comedians didn't think about it. And then suddenly a couple of comedians figured it out, and everybody else had to ask, oh, do I have to have a website now? Do I need to be on MySpace? I need to do Facebook? Do I do Twitter? And do I have to have a podcast? Each comedian has his or her own internal struggle between dreams and laziness now.

"You have to spend a lot more energy marketing and promoting than you used to, and that's a bummer. And you have to do it in such a delicate way that it doesn't look like you're marketing. And so, it's like, what do you want from me? You want me to be funny. You want me to deliver it to you for free. And you don't want me to overstep that so you feel like I'm pushing it on you. That's a really hard balance to strike. And when you do overstep, they say stuff. Like, 'Hey Greg, why don't you do some more live reads on your show? I'm trying to listen to a podcast.' I just want to go, 'It's FREE! I'm giving you free content twice a week, all you've got to do is push a button.' And in terms of Twitter, I actually love Twitter, because I have ADD. When I think of a thought, I wrote down that joke I told you before about the one black guy, I Tweeted it! If I've got that one quick thought that I can't get out of my head because it's so funny, boom! And if it's a thought that I had, I look before I go onstage, I look at my Tweets, and that's my setlist, right there. And people like it. But again, one or two a day. I think if you go beyond that, people unsubscribe, because they don't want to be hassled, and I always do at least three funny things before I say, I'm at Carolines tonight at 7:30. I feel like you've got to earn that promotional Tweet. I don't know if that's right or wrong, that's just my gut on it. I always think, I've got a Webmaster now and she's great. If you can find somebody who can do some of the grunt work on your website, if you can find a producer who can do your podcast. Granted, at the end of the year I lose money on my podcast. It actually costs me a fair bit of money to keep it up, but I know that it's drawing more people to my shows, so I hit some bonuses. And I know that I'm learning how to be a better broadcaster every time that I do it, and I believe that there will be more advertising for it at some point."

At least this kind of promotion is all in your control. It's not like when you do the promos that comedy clubs direct you to do.

"It's total control. The podcast: People complain about having to do this or having to do that. You don't have to do it all. You've got to find the thing that works for you and then be consistent with it. It's all consistency. People have to know what they can expect from you. This summer I was finishing the book and I did one podcast a week. The screaming I got, like !!! exclamation point screaming, and it's flattering. But you give people an expectation and you have to deliver that. If you're going to Tweet once or twice a day, you've got to keep doing it. I look at the podcasting as like, tell me what would be the best job in the world for you? How about sitting alone in a room with a recorder and saying any funny stuff I want and not having to travel and then blasting it out to thousands and thousands of people. That's a pretty sweet job description. Now if you look at the money from it, suddenly it's not a good job description. Fortunately, I can do other things and make the money. But I feel it. I feel that podcasting is viable. And when you have to make priorities about where you put your career, podcasting is becoming more and more a slice of the pie."

But at the same time, if you're reading this, your advice remains do not get into comedy.

"Do not get into comedy! If you're going to do it, you have to have to do it, you have to need to do it. If you have a Plan B, then you do not have a Plan A with comedy. There's no net. And that fear has to drive you. I've been working with fear as my main motivator to this day. Most of the comics that I like, we all think it's going to end tomorrow. And so we write harder. We work harder. We promote a little more. We're more neurotic than we need to be, and that's what it takes. And if you don't have that level of self-doubt and insecurity and need, you're never going to match up. Unless you're Dave Chappelle. There's these guys who come around once every 10 years who just kind of stroll in and blow everybody away, and then get high."

And that's a lesson for the kids.