To outside eyes, Greg Giraldo was an undeniable success. From all appearances, he was riding a bullet train to fame and securing a comedic legacy that would last the length of time itself.
In Los Angeles, Laugh Factory owner Jamie Masada called him a “Doctor of the Soul,” comparing Greg to Richard Pryor, George Carlin, Rodney Dangerfield and Robin Williams.
In New York, the Comedy Cellar’s Noam Dworman said, “He was handsome, he was tall, he was athletic, he was smart, he was likable, he was as quick-witted as Colin Quinn or any of the great comics, Seinfeld, or any of them. He was in their league and they knew it.”
But one lone voice held a harsh and dissenting opinion. That voice was Greg Giraldo’s.
In 2009, in a famous Psychology Today interview with Jay Dixit, Greg said, “It’s hard to distinguish when I was actually struggling from when I only felt like I was struggling—which was pretty much always … I’m a total fuckup… I’m constantly tortured by a sense of failure. I feel like quitting all the time.”
Sixteen months later, Greg Giraldo was dead of a prescription drug overdose at the age of 44, leaving comedians and fans in a permanent state of mourning and bewilderment. Who was the man between the praise and that last lethal fix?
In the new book Greg Giraldo: A Comedian’s Story, authors Matt Balaker and Wayne Jones uncover the mystery. They include personal stories from the people closest to Greg, including his former wife MaryAnn, scores of comedians including Jim Gaffigan, Colin Quinn, Marc Maron, Natasha Leggero, Nick Di Paolo, Eddie Brill, and Nick Swardson, plus friends from childhood, Harvard Law, and Greg’s short-lived tenure at Skadden Arps, one of the most prestigious law firms in the world.
The authors also explore the rough terrain of stand-up comedy in all its peaks and pitfalls. Did you know that Jamie Masada was so shaken by the number of comedian suicides that he hired an in-house therapist at the Laugh Factory?
The book soars from page to page with gripping and unexpected details in every chapter. At Skadden Arps, Greg hated the grinding pace but found hilarious subversive ways to puncture the stuffiness. As a comedian, he was uniquely effective when it came to reaching all audiences, roasting celebrities, handling hecklers, and even punking Robin Williams. There’s also a scene involving a hotel room and the calamitous demise of a hoard of Oreo cookies. The book is as memorable as the comedian himself.
Matt and Wayne also reveal the ups and downs of Greg’s two marriages, his shame and ambivalence over his stop-and-go television career, and his generosity to young comedians from contestants on Last Comic Standing to Chicago’s own Patti Vasquez.
The result is a profound and intimate biography. The physical pages seem to fall away, transforming the reader into an up-close, in-person witness to an extraordinary and tragic life.
Matt kindly spoke with me by phone about this first and only biography of Greg Giraldo.
WRITING THE BOOK
Teme: I loved reading your book! How was the experience of writing it?
Matt: More than anticipated! We tell the lesser known stories of Greg Giraldo’s life focusing on those that knew him best. It took more than three year to happen, but it was important to not rush it. It took time to reach out to publicists and sync up interview schedules.
Teme: Were there any surprises?
Matt: There were several surprises. We got more color on Greg’s days as an undergraduate at Columbia and we talked to some of the girls he dated when he was a teenager. The book will include a lot of photos, including from when he was a teenager and some funny ones from when he was a frat boy at Columbia. The book will have a nice scrapbook element to it in addition to stories that haven’t been told until now.
MATT’S FAVORITE STORY
Teme: What is your favorite Greg Giraldo story?
Matt: Greg worked with Jesse Joyce on some of the [Comedy Central] Roasts and Jesse had a big hand in many of the jokes. Jesse was also his opening act. After the Roasts, Greg would invite Jesse to the Comedy Central after-parties and make a point of telling the executives there that Jesse wrote those jokes. That’s something that could have detracted from his reputation, but Greg felt it wasn’t just about him. He was a very generous mentor.
Teme: You have a story about Greg doing a show at Zanies in St. Charles (Illinois) on the heels of a fight with his wife MaryAnn. How did you learn about it?
Matt: We interviewed a guy who was at that show. He and his wife happened to meet up with Greg for food afterwards and he told them about the phone call with MaryAnn and how they were both upset that he had to be on the road longer than planned.
Teme: You also write about his friendship with Patti Vasquez. She is a wonderful, well-known Chicago comedian and radio show host on WGN. But I didn’t know that she had a history with Greg Giraldo. How did you and she connect?
Matt: Paul Farahvar is a Chicago comedian who is also a lawyer. He did our legal review. Paul put me in touch with Patti. Like Greg, Patti is very smart and she and Greg hit it off. Another theme in Greg’s life was that he was very gentlemanly and looked out for others. He would be the one who would drive women comedians home at night. He treated everyone well. Jessica Kirson and others have similar stories of how he looked out for them, even very early in their careers.
Teme: I loved reading about Patti. I first saw her over twenty years ago. She was always a great comedian, even early on. So it was cool to read the stories about her and Greg from that time.
Matt: She’s also very humble. She mentioned that she had been at Stand Up New York, not having the best set and Greg walked out. Then they reconnected after one of her shows where she said she projected a lot more confidence. I think Greg liked that and they hit it off.
Teme: I was impressed with the stories about Greg’s generosity. Were you disappointed by anything you learned?
Matt: This book isn’t meant to canonize him because he had flaws like we all do. Something that disappointed me was that there were people who helped him when he was young, not just comedians but friends he grew up with, and as he became more ensconced in entertainment he lost touch with many of them.
There were people in his life that really helped him when he needed it. I think some of them felt a little let down. As he was going through his own struggles, he wasn’t able to be there for him like they were for him. It’s understandable but still disappointing.
MENTAL HEALTH AND FEELING LIKE A FAILURE
Teme: Did the book go in any unexpected directions?
Matt: One thing that changed is the emphasis on mental health, both Greg’s and more broadly, about comedians and even people in general.
When I started the book, I didn’t appreciate the link between mental illness and addiction and how prevalent the problem is. We talked to psychologists, psychiatrists and addiction experts. I don’t know for a fact that Greg Giraldo had depression, but he had symptoms consistent with depression. Until you address the root cause, the addiction is a symptom and you probably won’t improve. That’s an aspect I didn’t anticipate when I started the project.
Teme: I think a lot about the Psychology Today interview where he insisted he was a “fuck-up.” But he was nothing of the sort. Were his parents super critical or was it the pressure of being the child of immigrants who had sacrificed? What was the root of his persistent sense of failure and self-loathing?
Matt: I don’t know all the inner workings of his family, but he was a great role model to his younger siblings. It seems he had a wonderful upbringing and a loving mother and father.
For many people, it’s a brain issue. Greg discussed having “imposter syndrome,” a belief that you’re not good enough even though those feelings aren’t consistent with reality. By all accounts, he was not only good enough, but exceptional. But sometimes it doesn’t matter. Sometimes I’ll be in an airplane and we’ll hit some bad turbulence and I know that it’s nothing to be worried about, but my palms are sweaty and I’m gripping the seats and I tighten my seatbelt and it’s not logical. Anxiety problems are sometimes beyond logic.
We don’t know what was really getting at Greg. It sounds as if he had a depressive disorder, but that’s just speculation. It would have been wonderful if he could have taken time off to address it. But comedy was the thing that brought him joy.
MORE LIGHT ON THE PSYCHOLOGY TODAY INTERVIEW
Matt: I was so happy that we interviewed Jay Dixit, the Psychology Today writer who interviewed Greg. That article made the rounds with a lot of comedian friends and it spoke to many. One thing Jay advised, which is hard but not impossible, is to remember the smaller, more mundane things we have and realize, “Okay, my life isn’t horrible.”
But gratitude is an ongoing process as is understanding that it’s okay to feel down. Resiliency takes effort. It’s important not to get so hung up on expectations. In the chapter “A Comedian’s Mind,” Natasha Leggero said she knows only two comics who are happy with their careers. Part of that is comedians tend to compare themselves to others. It’s a natural instinct, but it’s also a recipe for constant insecurity and discontentment.
Teme: That thinking resonated with me. Did it resonate with you, too?
Matt: Oh, sure. Anyone who performs has a sense of “I haven’t gotten that Netflix special” or “why aren’t I making more money?” It drives you to improve, but it also takes away from the reasons you’re doing comedy, like because it’s an enjoyable outlet or you have something to say. It’s super easy to get caught up in what you haven’t done or who’s doing better, and lose sight of what you’ve accomplished.
Teme: Jay Mohr says in the book that he wished that Greg Giraldo had been more truthful to himself. What did he mean by that?
Matt: I think he meant that Greg should have treated himself better. He treated others really well but was harsh on himself. And maybe for him to acknowledge that while he had his struggles, so does everyone else.
Teme: If you could go back in time and give the book to Greg, do you think it would have helped to read how beloved he was? What would he think?
Matt: He’d probably think I spent too much time. Greg was very appreciative that Jay Dixit talked to him and wrote the article. Another journalist, Conor Hogan, interviewed Greg early in his career and Greg sent a really nice email thanking him and saying how well written it was. So I think Greg would be appreciative of the effort.
THE FATAL DOSE
Teme: The book tells a story about Greg alluding to his death. Was that the depression speaking or did he actually know his death was imminent?
Matt: He had really bad times when he was spiraling and probably felt the odds were against him. But it’s hard to know exactly what was going through his mind when he said that.
Teme: I was upset to read that a fan gave him the painkillers that led to his death. Do you know if she felt responsible?
Matt: We grappled with that. I want to be clear. It’s not her fault that he overdosed. If it wasn’t her, it would have been someone else. He put the substances in his body. It’s like blaming the car for a DUI. Perhaps it was an accessory, but I don’t fault her. If I overeat and I get diabetes, I’m not yelling at my fork.
Teme: If I have diabetes and someone brings cake into the house …
Matt: Point taken. But when you’re someone’s fan, you want to be in their good graces. Something I admire so much about his wife MaryAnn is that she had the courage and the strength to stand up to Greg and say “I’m not going to allow this.” But sometimes as a fan, you don’t really think long term. You just think “I want to hang out with this person tonight because it’s a cool story” without having their best interests in mind. This fan represents people at every tour stop, so I don’t want this to be some bashing of her. We didn’t actually talk to this fan. She probably has a side of the story, but we had enough people attest to her presence that we’re comfortable putting it in the book. But he’s the one who did it and he was in a bad place even before she got there.
IF YOU COULD TALK TO GREG …
Teme: If you could bring him back for a day, what would you ask him?
Matt: I’d want to know what his favorite food was. Some people said cheeseburgers. But that’s a minor thing.
I’d want to know if he really wanted to do the TV shows. We heard conflicting reports. Some said, obviously, he’d like the money. But I wonder if he would have been better off taking the Brian Regan approach where you just do the road and become really good at it.
I would have liked to know if he ever planned on not roasting. When he died, he was still known for Roasts, but I can’t see him taking the Jeffrey Ross approach where it’s what he emphasizes.
But if he were here for one day, I’d say, “go spend it with your family and don’t talk to an idiot like me.”
LESSONS IN COMEDY
Teme: What lessons can up-and-coming comedians learn from Greg?
Matt: Greg emphasized the importance of writing and not just getting up there and winging it. Write, flesh out ideas, perform, see what happens on stage and re-write. Another lesson he had is that the audience has the final say. You might be really attached to a joke, but if it doesn’t work with audiences, let it go.
Teme: How did Greg Giraldo influence comedy overall?
Matt: He talked about politics, but he was fairly non-partisan. Many comedians are social media activists and can sound preachy. He proved that you can entertain people with differing viewpoints and make them all feel welcome. He could poke audiences in a way that made people question their beliefs without feeling that he was talking down to them. He wasn’t didactic. He didn’t go up there and try to preach. I think that’s an amazing influence.
He also brought more attention to the Roast and had a favorable influence on insult comedy. Overall, he made intelligent comedy more accessible.
Teme: It was amazing how he could get his point across and still be really funny and reach everybody.
Matt: Yes, that’s also a reflection of his emphasis on writing and preparation. The power of writing and preparing are also part of his legacy.
Teme: How do you think he wanted to be remembered?
Matt: Probably as a great comedian and a known road performer. As much as he discussed doing a sitcom, he got the most joy out of live entertainment. He was a prolific, intelligent, broadly hilarious comic who entertained people across the country.
Teme: Why is Greg’s story relevant today?
Matt: Many people long for a career that they don’t have or want something more exciting, but few of us are willing to risk it. People who flirt with entrepreneurism will also get something out of it.
His story is also for those of us who tend to be very academic. He was book smart, but his greater talent was knowing how to appeal to so many different audiences.
We can also learn not to hold ourselves up to a perfect standard like a lot of comedians do and as people who struggle with mental illness often do. It’s okay to have faults. We all do. His story is also a reminder to be grateful for what we have and for the people in our life.
That also means that if we know someone who has an addictive personality or struggles with drinking or drug use, we’ve got to enjoy and appreciate them while they’re here. I can’t fix someone’s drug problem, but I can love that person regardless. I think that would be a good message for all of us. We’re only here for a very finite time, so let’s enjoy the time we have and try to appreciate the people around us.
Teme: Wow, that’s uplifted me just hearing that.
REMEMBERING GREG GIRALDO
Teme: How do you and Wayne hope Greg Giraldo will be remembered?
Matt: As a success. Greg should be remembered as one of the most influential, best comedians of the 21st Century. He could take a room full of people from all walks of life who didn’t know who he was and he could entertain all of them. Greg could do that better than almost any comedian that’s ever lived.
Greg Giraldo: A Comedian’s Story is available in paperback and on Kindle at Amazon.
More about Greg Giraldo: A Comedian’s Story and the authors at greggiraldobook.com.
My 2017 interview with Matt about the book’s beginnings is here.
Book signing and discussion with Matt Balaker on March 28, 2019 at 7:00 p.m. at Book Soup, 8818 Sunset Blvd. in Hollywood, Los Angeles, CA.
Stay up to date with all news and events (including Matt’s upcoming interview on Jeff Ross’s podcast) at greggiraldobook.com, Twitter, Instagram, and Facebook.
Do you have a radio show, podcast, blog, or email list that can help the authors spread the word about Greg Giraldo: A Comedian’s Story? Would you like to host a book release party in your hometown? Do you have the resources to help make this book into a movie? Please contact Matt and Wayne at greggiraldobook.com.