The Sound of Young America: Comedian Greg Fitzsimmons

Episode notes

Greg Fitzsimmons is a standup comedian. His memoir is Dear Mrs. Fitzsimmons: Tales of Redemption from an Irish Mailbox.

JESSE THORN: It’s The Sound of Young America, I’m Jesse Thorn. My guest on the program is the comedian Greg Fitzsimmons. He’s not only one of the nation’s most popular standup comics, having appeared on basically all of the venues that are available to standup comedians, including multiple comedy central specials, almost all of the late night shows, and more; he also has his own talk radio program on Sirius XM Radio, the Greg Fitzsimmons show; his own podcast, FitzDogRadio, and he’s the author of the new memoir Dear Mrs. Fitzsimmons: Tales of Redemption from an Irish Mailbox. It’s not just the story of his life told through his words, it’s also the story of his life as told through a giant pile of disappointing letters that his mother kept from his elementary school days all the way through his career as a standup comedian. Greg, welcome to The Sound of Young America.
GREG FITZSIMMONS: It’s an honor to be here and in good company with some of my favorite comics also, so I appreciate you having me in.

Click Here for a Full Transcript of This Interview.

JESSE THORN: I should mention that there are a lot of standup comedians here with us right now.
Yeah, it’s a lot like that boulevard of broken dreams, except with comedians.
JESSE THORN: Absolutely. I’ve always considered myself a radio Edward Hopper. Something about the desolation of the American urban landscape.
GREG FITZSIMMONS: Staring into a coffee cup looking for that next punch line.
JESSE THORN: Captured perfectly. Tell me about how you happened upon the stash of materials upon which this book is built?
GREG FITZSIMMONS: I guess about ten years ago I’m looking through my aunt’s basement in the Bronx, I’ve got boxes and boxes that are stored and I find one that was my mother’s that was filled with letters. I was curious – – a little bit inappropriately I started going through them, and she had saved every time a letter was sent home from school. There were two reactions, they would open it up at the dinner table – you know, Irish dinner, so it’s like a lump of mashed potatoes that were pink because of some bleeding meat laying next to it, and my dad would be smoking a cigarette, and he’d open up an envelope, and if it was funny – – the best is when a teacher quotes you, and then sends it home to humiliate you. But what they didn’t understand was that if my parent’s found it funny, we all laughed and you were off the hook. And then the letter was saved, and then one day you publish it.
So I gotta thank my mother for this, even though the book actually goes deep also, because it’s about authority, it’s about doing the opposite of what you’re told to do and about the American psyche and our whole creation myth is about being rebellious, and as an Irish person it goes back to the old country, too. It kind of tracks how I became somebody who always did the opposite of what he was told and where it got me.
JESSE THORN: Your book is full of these original source materials. First-person source documents. And I want you to read this disciplinary notice from Washington Irving Junior High School in your hometown of Tarrytown, New York. This is from 1980, how old were you?
GREG FITZSIMMONS: This is 8th grade, so I guess I’m about 13 or so; starting to hang out with the bad kids at this point. I went from hanging out with the nerds to gaining acceptance from the cool tough kids by being the funny one who would do crazy things. So – –

Description of incident:
Greg was loitering in the hall the other day with several other students when I walked by on my way home. Greg then began openly mocking me by making fun of my name, i.e. “The grass looked very Dewey this morning”, [Oh, you have to know is name is Dewey.] “Dewey have any homework?” And, “Are we going to learn the Dewey Decimal System?”
At first I ignored him, but eventually I felt I need to take some action. It is disrespectful and rude to address a teacher in such a manner, and I think it best to bring it to his parents’ attention.
Signed,
Dewey Ectal
JESSE THORN: What I love about that thing and what I was laughing out loud at is that those are really dumb jokes even for an eighth grader. They’re so epically dumb.
GREG FITZSIMMONS: So dumb. I was in a band then, we had a band in 7th and 8th grade, I played bass, and we wrote our own songs. One of them was called Dewey Ectal, and it was all those jokes put into verse. We had a very Dada sense of humor back then; Uncle Floyd was very big in the tri-state area, I don’t know if you ever watched that. But we watched Pee Wee Herman type sense of humor; just anti-authoritarian, kind of Marx Brothers. It wasn’t about the quality of the jokes, but about the inappropriateness of them.
JESSE THORN: That’s what’s so wonderful about it. That series of insults, the content is completely irrelevant to what’s going on, and I think the content is so intentionally – – you’re not swearing at him. You’re really making 1946 quality humor.
GREG FITZSIMMONS: Yeah.
JESSE THORN: And it feels like such a thing that’s just about you making the point that you can and will continue to make jokes at his expense indefinitely.
GREG FITZSIMMONS: Especially when, by the letter of the law, I have not insulted him. You leave yourself – – as thin of an out as you have left yourself, it does exist. And a lot of the jokes we did – – I can remember we were learning phonics at that point, and there was a board with multiple “p”s to show the different ways – – and we were up there to spell different things, and I spelled a curse word; but, the curse word has another meaning. So there was that tiny window. The teacher was angry, and she screamed at me, “I know exactly what you mean.” My friends were falling on the ground. But I knew – -what are you gonna say? Take me to court. There’s another meaning for that word.
JESSE THORN: Your description of your high school years at this fancy – – I mean, anytime you have “day” in the name of a school, I feel like you can safely assume it’s a pretty ritzy operation.
GREG FITZSIMMONS: Yeah, Barbara Bush graduated from the school. 1874.
JESSE THORN: I really started imagining a more wiseacre-y version of Max Fischer from Rushmore. Especially once you described founding the golf team, as far as I could tell, so that you could have a venue for drinking.
GREG FITZSIMMONS: You can’t golf without a drink in your hand. It is odd, because I think when you write a memoir or you’re seen as a renegade, you associate somebody who is James Dean, jeans and a t-shirt, and he’s kind of poor, and on the wrong side of the tracks. I think the point the book is trying to make is that every American, no matter what you do, in some way you have to have within you some part that feels rebellious. Whether you’re a school teacher that after school goes off and shoots guns at a range, or you’re some type of a priest – – bad example. I think for me it’s about showing that I did grow up upper-middle class, I went to a good school; but at the same time I was completely an American and an Irishman in the sense that I could not be told what to do. And if you did, you faced anger, violence, dissension, and it was about collecting people to do it with me. That’s part of it. I think individual rebellion is one thing, but the American version of it is, “No, we’re going to get a bunch of people, and we’re going to throw the tea into the harbor.”
JESSE THORN: I had a high school English teacher, and I was frankly a very poor student through middle and high school myself. I had a high school English teacher who once wrote a note on one of my papers that said, “Jesse – I’m worried about you. Is there anything in life that you take seriously?”
GREG FITZSIMMONS: At what age is this?
JESSE THORN: This is when I was about 16.
GREG FITZSIMMONS: I don’t know a 16 year old that does!
JESSE THORN: I showed it to my mom, mostly because at that point I had divorced myself from the idea of academic success, and I thought it was funny, I guess, that he would write this. He seemed genuinely sad. I showed it to my mom, she, to her credit I think, sort of flipped out. So wow, this is really not an appropriate thing to write on a 16 year olds paper. So she went in and took the English teacher to task in a meeting. I remembered very distinctly that that was a really big moment in my life, and you have a really similar moment that you share. One of your high school English teachers writing something on your paper. I wonder if you could read that.
GREG FITZSIMMONS: This was a guy – – I compare him to Donald Sutherland in Animal House. He was kind of that hippyish teacher who was a real academic and was deep, but he also had a romantic side to him. Every paper I wrote in school, the only way I passed was to try to get creative. I could not possibly put together a linear study of the Battle of the Bulge, so I would write something funny, and usually charm my way into getting at least a C minus on it. So on this one I rewrote Act 2, Scene 2 of Romeo and Juliet, the balcony scene. But I did it in modern times as two guidos, and his IROC is around the corner, and she’s up on the second story of the tenement. The comment he wrote on the paper was:
While I’m not quite sure this demonstrates a profound grasp of the scene, I have to admit it’s funny. Did you ever think of doing this for a living?
And I think literally – – I was never a good athlete, I clearly had not been doing well in school, and this was the first time in my life where I thought, “Wow. Somebody who is in a position of authority had confirmed something I had wished for.” Something that I felt like there was spark. I can read, I can write, I am funny; and now somebody who I really respected was saying, “Go for it.” And I never looked back. Literally from that moment forward I felt like “You know what? Mr. Jones said that I can do this for a living, and I don’t need anyone else to tell me.” You have to have that kind of conviction to make it in a business like this. To me, I guarded that comment. I found it in other teachers in college, because my confidence began growing as I got older and suddenly started playing sports in college; and I was good! Oh my God, I’ve always been good at this, I’ve just never had confidence!
Years later he tracked me down. There was a piece in the New York Times about me when I had a show on MTV. He looked me up and got in touch with me, and he remembered – – you gotta picture a teacher who has how many classes coming through every year, and we’re going back 20 years now. And he finds me and remembered that I had renamed the character Crustacea from – – I don’t even remember the book, and it was so touching that it wasn’t a one-sided thing, where maybe he just encourages everybody. He found something in me that he remembered, and it was that much more meaningful to know that all those years later, he really meant that.
JESSE THORN: It’s The Sound of Young America, I’m Jesse Thorn. My guest is the comedian Greg Fitzsimmons. He’s won multiple daytime Emmy’s for his writing on the Ellen DeGeneres show, he’s been on more or less every late night talk show, and has had multiple comedy central specials. His new book is called Dear Mrs. Fitzsimmons: Tales of Redemption from an Irish Mailbox.
So when you were just about to finish high school you had your first standup comedy gig, and you managed to get the microphone turned off and had to yell the second half of your set. Tell me about that experience.
GREG FITZSIMMONS: I’m 17, and there were a little bit of substance issues going on before the show. I was mostly doing Bill Cosby and Bob Newhart chunks mixed in with making fun of the teachers. Specifically there was a Western Civ. teacher that was having a long standing sexual affair with the art teacher, who was smoking hot. It was a great little rumor that was pretty corroborated by the fact that every time there was an overnight field trip the two of them would chaperone it. So I started doing jokes about them and they were in the audience, that’s when I thought the mic was broken, and I looked over and the principal was standing there.
JESSE THORN: Holding it up in the air like you were in Ferris Bueller or something.
GREG FITZSIMMONS: Exactly! It could not have been more of an image from that. I looked at him, and he was smiling at me, and I just smiled back, put the mic down, and screamed the second half of my act. I can remember walking off stage, and out the side door to the outside, I can remember literally yelling at the top of my lungs; like I could not contain the joy that I had. I wanted to do this since I was seven years old. I memorized every comedy album. It was everything I hoped it would be and more.
JESSE THORN: I would say a solid 20% of the letters in this book, and it’s a book that’s full of source documents, are from people who had hired you to perform; had made some request of you, like don’t swear; and then you had gone on stage and spent the first chunk of your act complaining about and defying whatever that request was. There’s one that’s in the intro to the book, and I wonder if you could read a little bit of it. It’s actually a letter to your booking agency.
GREG FITZSIMMONS: This is from a high school prom show. I was on the road doing a lot of colleges; I did a ton of colleges when I was starting out. Mixed in my agent asked me if I’d like to do a high school prom show in Iowa. I didn’t know Iowa that well, I didn’t really know the Bible Belt very well. I got there and the entire senior class was getting off the school bus because they had gone to church prior to the prom beginning and I’m immediately looking at that, and I’m looking at these kids that all have short hair and they’re all nice and everyone’s white. It struck me as, wait, this is prom night. I’m thinking of my prom night where there was drugs and booze and trips into the city. A lot of sexual – – I mean, American Pie. What is the prom? It’s your last gasp of rebellion and being wild. Then I get this principal that pulls me aside and tells me not to be a wiseacre up there. Every button has now been pushed in me. Comedy to me is anti-authoritarian. You do the opposite of what you’re told is the definition of comedy. Here’s what’s expected, and then you step on a rake.
JESSE THORN: I like, “Don’t be a wiseacre.”
GREG FITZSIMMONS: I don’t even know what a wiseacre is! I’d never heard the phrase. I’m thinking we’re out here in the country on a farm, he’s talking about acres? I got a standing ovation, and my agent received this letter and then forwarded it on to me. I was initially very upset about it, but to let it out I started reading the letter on stage, and then eventually did it on one of my specials on Comedy Central.
Dear Ario:
We held our HIGH SCHOOL PROM this evening, and our entertainment was comedian Greg Fitzsimmons. Let me be very frank: Mr. Fitzsimmons performance was one of the most humiliating, embarrassing, and degrading performances I have ever witnessed as part of a high school activity.
What makes it most unforgivable is that before his performance he was told about taboo subjects, (language, etc.) by Dr. Sam Dickson and myself. Throughout his performance he freguently referred to the dos and donts of our discussion. He apparently found it humorous to do exactly the opposite of what was instructed. His joked about having sex with his grandmother, inviting the class to his motel room for a keg, his talking candidly about the glories of cocaine, and other grossly inappropriate subjects too numerous to mention, were unbelievable.
If this is the only way he can be humorous, he and your whole company is sick, and should be embarrassed to market such filth. We try very hard to raise our children properly, and give them values.
If you’re questioning whether I’m a bible beater; no, I am not. I just feel that what we try so hard to instill in our young people can be dashed in one hour or less by some “comedian” that can leave town after doing his damage.
JESSE THORN: High school prom, by the way, in that first sentence, is in capitals and underlined.
GREG FITZSIMMONS: There was a lot of syntax that was really showing the anger underneath. He had to write this letter, he got some heat. He was CC’ing a lot of people on this letter, and he had to show outrage.
JESSE THORN: I get the impression that you have not abandoned that part of your ethos that suggests that should someone ask you not to be a wiseacre, the appropriate response is to be as much of a wiseacre as you can muster.
GREG FITZSIMMONS: Not as much. The truth is I have gone to a lot of therapy. I’ve been sober for 20 years, I try so hard. There’s just a part of me that feels like that’s my truth. I am here, I’m a gadfly. I am an archetype. Comedians, by definition, are supposed to challenge. When I see comedians – – I work on TV shows, I write on TV shows, and I’m in rooms of people that are just doing exactly what the network wants them to do. They’re providing formulaic crap. When I try to put stuff in that’s different, that’s edgy, it sneaks through and it’s why I’m there. I’m thinking, Why am I the only one here that’s trying to- – I’ve been on a lot of staffs where I’ve felt like there’s a lot of sublimation of anger, of point of view, because the money was there. The truth is for me, I feel like the money is only there because I’m being who I am, and I think that comedy today has become very commercialized. In my personal life there’s something I have to honor as an Irish person. When somebody cuts me off, I need to give them the finger. And if somebody is mean to my child, I need to take them and put them against a tree and explain what’s going to happen to them. I can’t stop that.
JESSE THORN: Something that’s come up on this show before that I think you write eloquently about in the book is that there is a style of comedy that is in large part about saying we’re all in this together. Whatever the venue for that is. It could be, “Hey, we all remember when this happened. That was crazy. The Kool-Aid man was crazy.” Whatever it is. Then there are comics who seem to pride themselves on a singularity of point of view, and almost bending the audience to that point of view. Bringing every single in that audience on board to something that is so distinctively and personally them.
GREG FITZSIMMONS: People say, what’s a good comedian, what’s a bad comedian? And I really think it’s such a simple definition for me. A good comedian works from the inside out; a bad comedian looks out at the audience and tries to determine what they want, and then they give it to them. The comedians that I watched, like Bill Hicks and George Carlin, they go deep inside and they live a life where they are processing what’s around them in their own way. And then they’re communicating that to an audience.
I’m not saying you should be up there being preachy, I’m saying first and foremost you gotta make a crowd laugh. Those are the tools you learn at first. You get your tool belt by going out and paying your dues, seven, eight, ten years on the road. After that you start to come up with material and you start to come up with confidence to where you can only go to the well of – – what makes me uncomfortable, what makes me embarrassed, what makes me angry? And then you have to go up and connect that to people in a way that – – I’m not trying to convince anybody of it, and I’m not trying to condemn anybody, but I am up there trying to say, “Here’s my truth. This is how I feel.” Some of the people I consider the best comedians, I don’t agree with anything they say, and I will stand in the back of the room and watch every second they’re on stage.
JESSE THORN: Greg, thank you so much for taking this time to be on The Sound of Young America.
GREG FITZSIMMONS: Honestly it’s an honor. I’ve been looking forward to this. Keep doing this thing. You’ve got my world out on the airwaves, I love hearing all of them.
JESSE THORN: Thanks Greg. Greg Fitzsimmons is a standup comedian. He’s the host of the Greg Fitzsimmons show on Sirius XM radio; Fitzdog Radio, the podcast, available in iTunes; his new book is called Dear Mrs. Fitzsimmons: Tales of Redemption from an Irish Mailbox.