7 years after death, comedy legend Greg Giraldo returns to spotlight in upcoming biography


Speaking to Matt Balaker I came close to slipping up and calling him “Greg.” Matt, along with Wayne Jones, are the authors of the upcoming definitive and only book about ingenious comedian Greg Giraldo who died of an accidental prescription drug overdose in 2010 at the age of forty-four.

Talking with Matt even by phone has the effect of bringing Greg Giraldo’s spirit back to life. The book’s insights are so fresh and keen that as Matt spoke I thought I saw Greg standing before me with his shaggy hair, amiable demeanor, and intellect as piercing and sharp as a surgeon’s scalpel.

Matt described the book, which he crowdfunded on Kickstarter, as “a labor of love” and “a passion project.” Wayne was first a supporter, but then offered his skills as a writer and librarian and the partnership was born.

Together they’ve gathered an illustrious and unprecedented group of forty contributors who have poured love, insight, and painful honesty into the pages. They include Jim Gaffigan, Marc Maron, Jim Norton, Colin Quinn, Nick DiPaolo, Nick Swardson, Natasha Leggero, Jay Mohr, Jesse Joyce, Laugh Factory owner Jamie Masada, Greg’s wife Maryann, and Greg’s manager, Rick Dorfman. I first heard about the book when Jim Gaffigan tweeted about it in 2015, urging his followers to back it.

The book traces Greg’s life from his years at Columbia University and Harvard Law School to his entrance and quick egress from colossus law firm Skadden Arps to the comedy clubs to television and to Comedy Central’s roasts where roastees knew to brace themselves for a gale-force when he took the podium. But as comedians, talk show hosts, and fans knew, Greg was not just an insult comedian. He could tackle any topic on the planet with equal and memorable ease (at least he made it look easy).

When you ask how people felt about Greg Giraldo, you hear the reverence. Jon Stewart showed it when he replaced The Daily Show’s “Moment of Zen” with a “Moment of Greg” on the day Greg died.


The universal admiration makes a 2009 Psychology Today interview with Greg even more baffling. There he revealed feeling like “a total fuckup … I’m constantly tortured by a sense of failure. I feel like quitting all the time.”

His are a life and mind deserving of more exploration, more behind-the-scenes insight and more celebration. Matt and Wayne’s book will deliver it all.

As fans wait for the release date, Greg kindly spoke with me … ack! See how I just truly wrote that and how this book makes Greg feel absolutely present! It was Matt who kindly spoke with me and shared some behind-the-scenes secrets about the book’s creation and what it will reveal about this comedy icon.


Teme: Where did your own love of comedy begin?

Matt: My dad took us to lots of comedy shows in the late ‘80s. The first I remember was Gallagher. I remember wanting to see Steven Wright, but my Dad thought he might be too blue. My parents also taped Evening at the Improv and I would watch it after school. Then in high school, maybe because I wasn’t too popular, I stayed in and watched Saturday Night Live.

The first time I did stand-up was in New York City in 2000. I was an intern at Conan and one of the other interns dared me. It was at Hamburger Mary’s, which I’ve since learned was one of the first places Greg Giraldo performed. I started doing comedy seriously around 2004. At first I did stand-up in New York City, and then moved to L.A. and trained at the Groundlings.

Teme: What about Greg Giraldo resonated with you and compelled you to write the book?

Matt: He’s been my favorite comedian since 2003-ish when he was on [Comedy Central’s] Tough Crowd with Colin Quinn. I didn’t have a Columbia University degree like him, but I was generally smart in school and I loved comedy, so I always looked up to him. I loved his brashness and how he was unafraid to be edgy without trying too hard to be edgy. It’s a difficult line to walk and he did it masterfully.

He was so consistent. From minute 1 to 59, he was always funny, topical, and unafraid. But he also seemed very friendly and that was something I appreciated about him, too.

The drive to write the book came when my wife was pregnant with our second child and I had to work more consistently. I still did comedy, but not as much as I used to. So I read about comedy and wanted to read more about him. I searched and didn’t find any books about him.

He’s one of the best, most influential comedic talents, and it seemed inappropriate that no one had written that book. And he has this interesting side story of being a Harvard-educated attorney who dropped out of law and I was fascinated by that. I thought, “Well, shit, no one has written about him. Maybe I’m the person to do it.”

Teme: How would you describe his voice?

Matt: Raspy… Really, he was culturally relevant without being on a soapbox. He was continually surprising. He could appear liberal, conservative, libertarian and anywhere in between. He was naturally intelligent without using five-syllable words to show off how smart he was. He was very unafraid, and in a way, also vulnerable. He didn’t try to play a tough guy. He was himself on stage and I think that’s admirable.

Teme: I wish he were here to tell us what he thinks about politics now.

Matt: I know. There are a lot of things I wish he could be here to talk about. That’s certainly one.


Teme: It always struck me as a by-product of his intelligence how he found the most accurate and precise words without ever sounding memorized or over-rehearsed.

Matt: That’s a good point. He had a controlled rant style. Although he’d have similar topics one show to the next, it was never delivered the same way. He continually wrote new material and part of it was just because he was so book smart. He could articulate thoughts simply, or I should say concisely, which is never simple.

Teme: Do you think that’s what made him so universally liked and admired among comedians?

Matt: There are a few reasons. One is that he was a stand-up comedian first and not a talk show host or actor. So he had a certain amount of street cred because of that. Two, he had an edginess. He was willing to take chances and tell jokes that would definitely put some people off. In the book, Jay Mohr has a really thought-provoking description of Greg’s comedic veracity. He was willing to pass on a show if he wasn’t passionate about it. If he thought a topic or an idea was trite, he wouldn’t do it. A lot of comedians want that integrity but if money’s in front of us, we’ll do it.

He was also really helpful to others. He wouldn’t step on anyone to climb the entertainment ladder.

He had a little bit of that underground vibe to him. People in comedy knew he was great, but he never really crossed over to the mainstream, which also endeared him.

Teme: What have you learned about him that’s been a surprise?

Matt: There’s a lot. The book will do a good job of uncovering that. One thing is that he seemed so confident on stage, but off stage he felt very insecure and uncomfortable in his own skin.

So many comedians feel that way. Whatever level you’re at, you want to be higher. If you’re doing bar shows, you should be doing clubs. If you’re doing theater, you should be doing stadiums. In some ways it’s not surprising because so many comedians are that way, but because he was so revered I was surprised that he didn’t bask in his success more than he did.

It’s also surprising how deep his addiction ran. He was a family guy and married and a father, so you might think, “well, this disease or these demons don’t run as strong,” but that’s not true. It was surprising just how real his addiction was.

Teme: I wanted to ask you about that because that Psychology Today interview was a lot of things I didn’t expect. What was the source of his pain and sense of failure?

Matt: One of his good friends, Joe Schrank wrote a beautiful piece after Greg passed. He’s an addiction expert. His point was that addiction is a brain issue.
It’s not as if Greg Giraldo was thinking “I want to party and have fun.” There was something that made him sad and depressed, and maybe it was the chemical thing in his brain. Using drugs and alcohol was a way to medicate.

Teme: I can definitely hear that. I was really moved by the difference between the way people perceived him and the way he perceived himself.

Matt: He achieved more in comedy than 99.99% of people who pick up a mic. His material is funny to this day. That’s so difficult to do. It’s hard to compare a joke that was funny in 1995 to one that’s funny in 2017. But his humor was evergreen, even the topical material, and that’s a talent that few other comedians have.


Teme: That’s such a good point. I was listening to his album Good Day to Cross a River before we talked and it hit me how everything feels so fresh and it’s still hilarious. Nothing is dated. It really is amazing.

Speaking of your contributors, you have a very impressive list. How did you go about reaching out and getting people on board?

Matt: Well, you need a willingness to ask and get rejected, although the response was generally very, very favorable. The first domino was Rick Dorfman, Greg’s friend and longtime manager. We had a mutual friend, Karith Foster, whom I know from stand-up. Karith was friends with Rick, so Karith emailed Rick Dorfman saying my good friend Matt wants to write a book about Greg Giraldo and wants to interview you.

Without that introduction it would have been a lot harder. Rick had great background information and opened the door to Greg’s wife Maryann. Each of them had suggestions and said, “Oh, you should talk to so-and-so.”

For example, Rick suggested I contact Jamie Masada, the owner and manager of the Laugh Factory. I didn’t know he was so close with Greg. It took a year and a half to get the interview. But it was Rick and Maryann and Colin Quinn who helped open the door to a lot of the others. Then it was googling and emailing and calling and requesting.

Teme: Do you have people from law school or Skadden Arps?

Matt: Both. We interviewed one of his best friends, Dave. There will be more background on him in the book, but he and Greg were roommates at Harvard Law and worked together briefly at Skadden. I also interviewed one of his best friends at Skadden Arps who was Greg’s first friend at the law firm.

Teme: Every facet of this book sounds so interesting. I’m intrigued by the fact that he walked away from Skadden Arps and from guaranteed prestige and financial security.

Matt: A lot of readers will identify with that theme. Everyone who isn’t a lead singer of a rock band has fantasized about doing something else. So many people have passions that just aren’t lucrative or they don’t think they can do professionally. When you’re a Harvard educated attorney, the opportunity cost is much greater than if you’re a 9th grade dropout.

Robert Kurson was a lawyer who went to Harvard when Greg did and is now an author. We interviewed him. He said that within the attorney community, what Greg did means he won. He had the courage. There is freedom to that, kind of a “fuck you” to it all where someone says, “Yeah, I know this is the safe route, but the hell with it. I’m going to get a notepad and tell jokes.”

Teme: In the Psychology Today article Greg said that he was incapable of being a lawyer. What do you think he meant by that?

Matt: There were several factors. One, he was a much better student then practitioner. Lots of lawyers will attest that law school is incredibly different from practicing. Different skill set. So I think he was great at school and could retain knowledge, but that he wasn’t very organized when it comes to detail-oriented legal work. He really wasn’t cut out for it. Not that he couldn’t have done it. But he didn’t go to law school because he always dreamed about being a lawyer. As a smart kid, it was a default.

As he was beginning to practice he realized, “You know, I’m not that good at this.” But when he started stand-up, he was the best one at the open mics right away. It was a validation that comedy is something he was naturally good at and enjoyed versus “I should be a lawyer because I feel pressure as the brilliant son of immigrants.”

Teme: How did he get involved with the roasts?

Matt: It was through Joel Gallen, who produced several roasts for Comedy Central. He saw Greg at local New York roasts and at the Chevy Chase roast on a different network. He said, “Damn, this guy is good.”

Teme: Even though his comedy is not just about the roasts, he was excellent at it.

Matt: And that was another thing that surprised me. When he talked about the roasts, he acted like it was a throw-away, “yeah, whatever, I’m doing a roast.”

But he took it seriously. He procrastinated, but when push came to shove he wrote religiously, just tons of material. It was like his work with Tough Crowd. He took preparation seriously and it showed in his delivery and his material.

Teme: What are some of your favorite Greg Giraldo lines?

Matt: One of my favorites is, “If we all grew up with self-esteem, who would dance at the strip clubs?” Also, when he said to Gilbert Gottfried, “you look like you smell like pee.” That one still cracks me up.

My favorite moment is the exchange he had with Denis Leary on Tough Crowd with Colin Quinn when Denis said about North Korea, “Of course they have to go to war. They’re a country with nukes that hates us. We hate them. The nukes are pointed at us,” and Greg replied “Oh yeah, like the big war we had with Russia.” That’s my favorite because it was improvised and to the point, but it was also very intelligent and withstands the test of time.

Teme: Denis Leary looked so angry during that exchange. Were there hard feelings afterwards?

Matt: There were on both sides. But please include this: Denis Leary was the celebrity guest at that show and Colin Quinn gave Denis the authority to nix that segment, but he chose to keep it in. So I think that is pretty cool.

According to the people I interviewed, Greg was also upset that the show was shot in a different sequence than it aired. So after that exchange happened, Greg appeared calm and quiet, as if he’d been taken down. But that wasn’t the case at all. Greg didn’t wanted it to look like he was afraid or had wimped out.


Teme: How has writing this book changed your life?

Matt: It’s given me less time and less money. It’s a fun process, but not an easy process. There are expenses I didn’t anticipate. There are people who want to talk to you and then they don’t want to talk to you and then there’s the whole marketing angle. There’s so much to getting a book out there that I didn’t know before I started. It’s given me more appreciation for the writing process.

It also opened my eyes to Greg’s family and friends and those people who were with him through the early days, how in so many ways they’re the unsung heroes.

Behind every artistic success there are people behind the scenes who never get credit. His family and friends stuck with him when things were really bad. They’re not going to be the subject of the book, but that insight has changed my life.

You would think, oh gosh, it would be so much fun to hang out with him because he’s so funny, so smart, so friendly. But it wasn’t always fun for the people who were with him. Some of it I’m sure was hell, like for his wife who was raising three kids. He had a support system. There were people who helped make Greg and who make any great performer who he or she is. Writing this book has helped open my eyes to that. My appreciation extends to all people who have loved ones with addiction issues.

Teme: Who is the book’s audience?

Matt: Fans of Greg Giraldo and stand-up comedians and fans of stand-up comedy. They’re the core. But I think any white-collar types who have fantasized about leaving their secure job for something else will get a lot out of it.

Teme: How can fans get in touch and stay up to date with the book’s happenings?

Matt: Twitter and the website are the best ways. We’re working to get the book out later this year. This book is a celebration, so while there are sad parts, my goal is to preserve his legacy in a positive manner. Anyone who has a story about how Greg Giraldo positively impacted you, contact us and your experience may end up in the book or on the web site. We also want to hear ideas for the title. This is a grassroots endeavor. Anyone who would like to help us publicize the book and get the word out, please contact me.


Matt Balaker
Matt Balaker
Wayne Jones
Wayne Jones

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