Here are some excerpts from this 2019 book:
* “Every day there’s a story in the paper about how shitty our schools are,” Greg Giraldo tells the crowd. Although he has performed this bit hundreds of times, his delivery comes off as instinctive and unrehearsed. With his right hand gripping the microphone, he pauses for a beat, and continues.
“I read a book—it was filled with letters that soldiers during the Civil War had written to their girlfriends back home. These guys were kids—they were 14-, 15-year-old kids. Most of these guys had never even been to school. But every single letter in the book was incredible.”
The onlookers go quiet for a moment as Greg alters his voice to mimic an exaggerated 19th-century Southern accent.
“My dearest Hannah. This morn finds me wracked by the fiery pangs of your absence.”
Laughter builds and quickly spreads throughout the Comedy Works audience. Before letting the chuckles subside, Greg continues: “I’ll bear your cherished memory with me as I battle the forces of tyranny and oppression.”
Speaking in his natural, slightly raspy New York tone, Greg says: “Now think about what the typical letter from your average modern-day soldier to his girlfriend back home in like New Jersey’s gotta read like.”
Adopting a New Jersey accent, Greg continues: “Dear Marie. It is hot as fuck out here.”
Applause mixes with laughs, and he resumes: “It is hard to fight these sand monkeys wit’ your balls stuck to your legs. It is very, very hot out here because I am in the dessert.”
Acknowledging the intentional mispronunciation of desert, the fans reward Greg with an extended applause break. Back in character, Greg punctuates the joke: “What else did I want to axe you? Oh yeah, don’t fuck nobody till I get back.”
* Gregory Carlos Giraldo was born on December 10, 1965, in the Queens borough of New York City. He grew up in a close-knit, Roman Catholic home with his two younger siblings—a brother, John, and a sister, Elizabeth—and their parents. Greg’s mother, Dolores, lived in Spain before emigrating to the United States. Alfonso, Greg’s father, was born in Colombia and worked as a fuel-purchasing manager at Pan Am Airlines.
Greg’s parents spoke only Spanish at home, and most of their family friends conversed in it as well. Greg heard English on television and on the playgrounds and streets of Jackson Heights, Queens, but nowhere else until he entered school. The dual linguistic heritage was a boon in practical terms, as Greg became totally at ease in both languages and gained knowledge of two foreign cultures—not to mention the American one that he was born into.
* Greg graduated from Columbia in 1987, and as he put it, felt “dragged along by fate” to enter Harvard Law School. Law school was a default choice rather than a lifelong passion for Greg. Some of his Columbia friends teased him about his academic choice. “How come everyone’s acting like I sold out?” he asked. Downplaying his acceptance, Greg told his friends that Harvard needed another Hispanic. Greg entered Harvard a year before another famous alumnus, Barack Obama, who had allegedly scored five to 10 percentage points lower on the LSAT than Greg had.
* His Ivy League education didn’t focus on vocational preparation. Instead, it emphasized philosophy, rhetoric, and debate—subjects Greg would later put to good use.
* After graduating from Harvard, Greg started working in September 1990 at the same international law firm where he had worked during the previous summer—Skadden, Arps, Slate, Meagher & Flom, one of the most prestigious firms in New York. To many in the legal field, a Skadden pedigree carried more cachet than even a Harvard law degree.
Skadden gained prominence in the 1980s when the firm was at the epicenter of a fervent mergers and acquisitions market. The real estate and Wall Street booms helped Skadden generate record revenues. In 1985, it ranked as one of the country’s top three largest law firms. Skadden lured young attorneys with its prestige and pay. Skadden practically built a pipeline from Harvard Law School. By the time Greg joined the firm, it had a sterling reputation, but money didn’t roll in as fast as it had in the ’80s heyday.
Greg’s summer internships were an unrealistic prelude to the treacherous and cloistered career he had now embarked on. Life at big law firms in the ’90s was a grind, not a job where Greg could phone it in. All-nighters were common. Those who worked more than 100 hours a week were praised by other lawyers in the hallways. Brainpower pervaded. Greg could use his entire vocabulary without appearing pompous.
Power partners, mostly overweight men, catered to executive clients of a similar ilk. Large bottles of Tylenol were displayed on mahogany desks like status symbols of the migraines the work caused. Other stronger and more addictive vices were hidden from sight. The chain of command was almost militaristic.
* However, pro bono projects were included too. Greg teamed up with Klein on one such task. It had nothing to do with defending the disenfranchised or fighting injustice. A privileged woman, who was friendly with a Skadden partner, wanted help setting up a nonprofit related to her dance studio.
How the hell did we get this? Greg thought.
The two office neighbors gave minimal attention to what they considered a waste-of-time undertaking. The high-society lady was so unimpressed with their work that she fired them. Greg was let go by a client who paid nothing. Experiences like these helped sharpen Greg’s ability to see multiple sides of an issue. We’re helping one bullshit corporation get the best of another bullshit corporation, he thought. He understood the good and bad in most sides.
* both disliked the notion that lawyers were easily substituted for one another, viewed as fungible assets.
* Greg was ill-suited for a career as a lawyer. In law school, he got by on his book smarts, but practicing law required keen attention to detail and relentless focus on organization—skills Greg lacked. And he knew it. Greg explained, “If you spend five minutes with me or watch me try to balance my checkbook, you can only imagine the disaster I would make of anyone’s legal issues.” Greg would occasionally show up for assignments with the wrong client’s files. One of his closest friends called Greg the most disorganized person he had ever met.
Real estate law was particularly inappropriate for him. Greg loathed poring through mountains of documents to analyze financial statements, lease agreements, title rights, and other deal minutiae. At Skadden, he would have to take orders from real estate partners before he could do any substantive legal work.
The desk work and the sterile office environment took a toll on Greg’s psyche. Law firm drudgery ate at him. Reviewing documents and dealing with law firm politics nearly broke him.
* “Most people who find out I’m Hispanic, they react the same way: “Like, wow, man, you don’t seem Hispanic.” They say it like it’s an enormous compliment.”
* Greg characterized “Spanish it up” as “a million examples of just fucking horrific retardation.” He mentioned that certain plot lines played off the worst kind of stereotypes. He shared an example of one involving a pregnancy scare with his girlfriend. “I guess they thought that she could be all stiff-upper-lippy and WASPy about it,” said Greg. “And I would be all proud Latino, like, ‘I banged that bitch and I knocked her up!’”
In a People magazine interview, Greg talked about the challenges of representing a culture. “Because I grew up in an Irish neighborhood, I never really identified myself with my ethnicity,” said Greg, who didn’t want to be viewed as “the torchbearer for all things Hispanic” just because he was on TV.
* Greg wanted to replicate the type of stable home life that his parents gave him, but he faced personal issues that made it more difficult to achieve. He couldn’t escape his feelings of inadequacy. Perhaps it emanated from some type of depression, but Greg’s mental distress impacted his family. It also caused him to seek remedies to treat his angst. Alcohol gave him a temporary reprieve.
* Greg and MaryAnn entered couples therapy—this helped Greg come to terms with his addiction and see that it was a diagnosed illness. But there were major challenges to overcome. During a session, the therapist told them that there was no point in going to therapy until Greg treated his own condition.
“You can’t go to therapy if you’re an active addict,” the therapist told Greg. “You’re not even going to remember anything that we’re saying.”
This message hit home for Greg, who felt incredibly guilty about what his family had to endure. It gave MaryAnn comfort, knowing that he had heard it from a licensed professional. Greg worked to improve his health, but he struggled. MaryAnn, who had witnessed her own father’s bouts with alcoholism, wanted desperately to help Greg. But she knew it was his battle to fight. She saw signs that were less obvious to others. She noticed that sometimes Greg’s hands would shake, a symptom of alcohol withdrawal.
As Greg’s drinking issues worsened, MaryAnn stepped up and worked feverishly to help maintain the relationship between her three sons and their father. The situation was serious. The family spent tens of thousands of dollars to send Greg to rehab. MaryAnn, however, thought about much more than just money. “All I want is for the kids to be able to spend time with him,” she said. “Because I don’t expect him to live.”
* [Jay] Dixit wanted to interview a successful comedian. By 2009, Greg had been doing comedy professionally for almost 20 years. Audiences loved him and comedians respected him. From Dixit’s perspective, Greg was the perfect counterpoint to failure. He connected with Greg. What transpired shocked him.
In his interview for Psychology Today in May of that year, Greg revealed that the outward success was not something he felt or saw in himself.
“I’m constantly tortured by a sense of failure,” Greg told Dixit. “I feel like quitting all the time.”
Dixit was surprised not only by Greg’s perception of himself, but by the open, honest, and thoughtful way in which he spoke. In Dixit’s long experience as a journalist, this was rare.
Several times, Greg referred to himself as a “fuckup” and criticized his perceived lack of resiliency. “I’m not a ‘get knocked down and just pull myself back up by my bootstraps and come back harder’ kind of guy,” he said. He admitted to “this constant feeling of not having achieved enough . . . the sense that I suck constantly . . . frustrated with myself and my limitations.”
Greg was not perfect, of course, and some of his harsh self-assessments were accurate. “I’m constantly tormented by the fact that if I could get organized enough to just sit down and write, I would be 50 times further than I am today, creatively,” he said. During his time preparing for Tough Crowd, Greg excelled under the constraints of deadlines and deliverables, but in the less structured environment of a comedy tour, his creative output flagged. He also received regular requests from film executives asking him for movie ideas, but after coming up with some concepts, Greg said, “I get all fucking ADD and the opportunity slips away.”
Apart from the ability to be a disciplined writer, though, Greg had many skills and accomplishments. Comedy clubs wanted him to headline. His peers admired his artistry. Television producers paid to work with him. Still, he criticized himself for falling short of his potential. High achievers such as Greg often hold themselves to unrealistic standards. In one sense, it helps them, it drives them, it pushes them past plateaus. But expectations can get so elevated that they create a constant sense of failure. Greg looked for examples of himself as a failure, and of course he found them. The cycle continued.
“It’s confirmation bias,” Dixit explained. “If you think you’re a fuckup, you’re going to find reasons to justify your belief.”
Greg’s issues with self-confidence became so severe that he wondered if he even deserved to be a comedian. “That was such an insane thing for a guy like that,” said Colin Quinn. “A lot of young comedians looked up to him the most by far as the guy they loved.” Greg worried about the effect of being perceived as unsuccessful, a “loser” whose projects never “take off.” He didn’t care about the lambasting he often got at the comedy roasts—he famously dished it out too—but he did worry that some people might conclude that the jibes about him were actually real.
“It’s not so much the jokes, I just worry that it will become a self-fulfilling prophecy,” Greg said. “Like, great, I’m Greg—the guy that kills fucking pilots. It maybe gets to me on that level. There’s maybe this little part of me that thinks, Fuck, maybe they’re right. I haven’t really accomplished anything they can make fun of.”
In conversations with friends, Greg discussed suffering from the impostor syndrome—an internal experience of intellectual phoniness that researchers say “interferes with the psychological well-being of a person.” The consequences are very real, and those impacted confront fear, stress, self-doubt, and feel uncomfortable with their achievements. The results can be debilitating, and the more success the person has, the more they focus on how much they are below their ideal, “strengthening the feeling of being a fraud or an impostor.”
* Greg became a staunch admirer of comedian Doug Stanhope. He respected how Stanhope always said exactly whatever he wanted to.
* Greg was not afraid to take risks on stage and he didn’t always play it safe with his material. This helped Greg stand out comedically, but the risky material sometimes clashed with his natural empathy. He could be overly sensitive to those who felt alienated or offended by his edgier humor. Many comedians are able to separate the two aspects of their person more categorically. Patrice O’Neal, who famously sparred with him, was one of those. O’Neal could cut hard at any topic or even an audience member, and he always laughed it off and just moved on. It doesn’t mean that he was heartless. He was just more able than Greg was to make the separation between what he was performing on stage and how it might affect the person he was talking about.
As an example, Greg and Schrank made a series of online videos, with one involving Greg interviewing a supplier of communion wafers used for the Eucharist in Catholic church services. Greg asked if the wafers came in different flavors, such as jalapeño for Latinos. This bit caused someone from his high school to send him an angry email. Greg took the criticism to heart. He worried that he had offended the entire Regis High community.
* In an infamous exchange between Greg and Denis Leary on the show, Leary himself remarked about Greg’s preparation. The incident occurred on May 7, 2003. Greg and Leary joined Lenny Clarke and Sue Costello on the Tough Crowd panel. Quinn steered the conversation to North Korea. Rumors had circulated that the country was developing nuclear weapons and pointing them toward the United States.
The comedians threw around suggestions on how to mitigate Kim Jong-il’s destructive tendencies while cracking jokes about his drinking habits and diminutive stature.
“Do you know how short you have to be to have a Napoleon complex in North Korea?” joked Greg about the five-foot-three dictator.
Moments later, Leary more sternly endorsed an American military action against the communist nation. Greg commented that “maybe there’s a nonviolent way to solve the whole North Korea thing.” Leary interrupted and mocked Greg’s point by proclaiming, “There’s a nonviolent way to solve a problem with the country that we hate, that hates us, that’s got weapons pointed at us? I don’t think so.”
Without hesitation, Greg replied: “No, you’re right, like Russia, for example, that big Russian war.”
The audience went silent—processing the sharp comeback—then laughter broke out in the crowd. Meanwhile, Leary looked at Greg stone-faced, pointing his left index finger in Greg’s direction.
Moving on with his planned material, Greg proposed that the two nations could temper their grievances by offering economic concessions: “I heard they’ll agree to stop building nukes if American women agree to get their nails done at least twice a week.”
Leary—displaying no reaction to the manicure joke—accused Greg of over-preparing. “This guy writes so many jokes before the show it’s not even funny,” said Leary. ”Unbelievable. He’s got, he’s got a pocket full of them.”
“That’s kind of what we do here, Denis, a little comedy writing,” said Greg. This line caused the fatherly Clarke to shout, “I’m not coming back.”
Leary countered: “You’re the guy in school who did all the homework and then asked if there was any more that needed to be done.” To which Greg snapped: “And if you had tried a little comedy writing, maybe your show would still be on the air.”
The atmosphere flipped from comedic to combative. With the two alpha males engaged in trash talk, Quinn set one foot on the coffee table that separated Greg and Leary, to play peacemaker. Quinn then said that the segment was over and alluded to a possible scuffle that might take place on the set. Before the lights faded out Quinn said, “This is as ugly as it’s gotten, and it definitely gets ugly on this show.”
This exchange between Greg and Leary has gone down as an epic moment in the annals of comedy lore. Comedian Steve Hofstetter called it “one of the greatest things I’ve ever seen.” Maron said, “There’s no better moment of television that I can imagine.”
Once the episode returned from commercial break, no ugliness or tension lingered. The comedians appeared undisturbed and joked almost dispassionately about fraternity hazing.
“Fraternities are great,” said Greg, referencing his college days. “If you get drunk and pass out, there’s always someone to pee on you.”
So why were things so calm? Details behind how the altercation went down add to its mystique. The portion of the show involving North Korea was a replacement segment and not part of the original taping. Quinn considered the first version too “boring” and requested a reshoot. The exchange between Greg and Leary was taped last but aired early in the show. So the reordering gave the appearance that nothing had carried over from the fight between Greg and Leary.
* As for Leary, he was more objective about the incident. “It was a great moment, where I really looked like a douchebag,” he said in an interview almost eight years after his appearance on Tough Crowd. “And I felt bad. In Greg’s defense, he actually—he was very prepared for almost anything that could have happened.” Quinn granted Leary the opportunity not to air the segment. Leary, however, insisted that it stay in, telling Quinn: “That was good TV.”
* Greg: “Of course blacks watch more TV: there’s not a hell of a lot to do in jail.”
* Greg responded: “The people that are in the media that review shows are a certain kind of upper-class, elitist type of person. They have a certain view of comedy. This show was more in-your-face, very blue-collar, down-to-earth, honest, not ironically distant, and they didn’t know what to make of it.”
* [Nick] Di Paolo: “Last night I was at The Stand, a club in New York, a little tiny club in there, smaller than the friggin’ Comedy Cellar. There’s two black gentlemen up front probably older than me. They had suit jackets on. They fucking loved me. I made a couple cracks about the riots in Baltimore. The rest of the room was fucking Johnny White NYU students. They’re getting all nervous and clamming up. The two black guys are howling. I’m talking to them. I said, “Look around,” to the black guys. I said, “Look at all the white kids afraid I’m going to hurt your feelings.””
* Jim Gaffigan also commented on the amount of rejection in show business and characterized the effect it can have on a performer as a “tax” quite unlike anything experienced by anyone in a regular profession, such as being a lawyer, where objective hard work and long hours will eventually get you the success, the money, and the partnership that you strive for. “In the entertainment industry,” Gaffigan said, “the rejection, the television show that didn’t work, the second television show that didn’t work, the five or six Comedy Central shows that didn’t work—there’s a tax to that.”
There was an extra shock in this for Greg because he had a pattern of success since childhood. He was successful in grade school and college and even in law school. That changed when he was in his late 20s and trying to break into the comedy business. The failures were difficult to stomach. “He was a great comedian,” said Gaffigan. “But his track record would have told him that he might not be a great comedian.”
* Dr. Ildiko Tabori, the in-house psychologist that Masada hired, has a unique perspective on the range of issues that impact comedians. She is a licensed clinical psychologist specializing in matters of the brain and behavior.
According to Dr. Tabori, addiction is not an independent affliction, unrelated to the rest of a person’s life. It is a coping mechanism. Happy people don’t abuse drugs. “If things are going great in your life, you’re not going to be smoking crack,” said Dr. Tabori. “Substance abuse does not exist in a vacuum.”
Dr. Tabori followed Greg’s career, and she noticed that the subject matter of his material seemed to reflect his mental state. “You can see him starting in a really great, positive place and being really successful,” she said, “and then things went awry. I don’t know what was necessarily going on in his personal life but you can see it in his comedy where he started to get really, really angry on stage, and it was dramatic, the difference.”
She surmised that most of Greg’s mental struggles didn’t start with drug use. “He was doing drugs because he was sad and depressed,” said Dr. Tabori.
She also speculated that a desire to perform often has more to do with low self-esteem than confidence. Some comedians view the stage as the only place where they can get attention. “And if they’re not center stage, they’re not comfortable and they start feeling those self-doubts,” said Dr. Tabori. “Somebody who is feeling secure doesn’t always need to be the center of attention.”
When it came to addressing the causes of his angst, Greg thought initially that alcohol and drugs helped him cope. He said: “I’m actually fixing my problem. I’m treating my illness.” Then he quickly learned that this approach didn’t work. “And then you try to stop, and not drink or anything, and all of a sudden that illness is still there with no medicine,” Greg said. “It gets fucking worse and worse and worse—until you address what’s wrong with you, then you’re going to keep picking up and going back down that path.”
