Most people would scoff at the idea of pivoting from a stable career as a lawyer to a career in stand-up comedy. But Greg Giraldo wasn’t most people.
An incredibly intelligent child, Giraldo attended the prestigious Regis High School in Manhattan, and from there went on to Columbia and Harvard. Eventually, he passed the bar exam and started practicing law. But through it all, he never lost his love of curse words or off-color humor.
Then, one day, he found a notebook of old jokes he’d written — and decided to quit his job to pursue a career in stand-up comedy. His bet paid off in just three years, when ABC offered him a prime-time sitcom, Common Law. Though it was canceled after just one season, it did the job of putting Greg Giraldo’s name on the map.
Giraldo moved on to bigger and better things, making regular appearances on late-night television shows and on Comedy Central, where he was particularly well-known for his hilarious celebrity roasts. But behind the scenes, Giraldo was battling substance abuse and imposter syndrome. And in September 2010, his career came to a sudden, tragic end when he accidentally overdosed on prescription medications and died in the hospital.
Tragically, that very same week, he had been set to introduce Courtney Love at the annual New York City Recovery Rally. The rally was meant “to celebrate the reality of recovery from addiction and offer hope to those who have yet to find recovery,” according to the event announcement. Giraldo never showed up.
Greg Giraldo’s Journey To Harvard
WENN Rights Ltd/Alamy Stock PhotoGreg Giraldo died of an accidental overdose after struggling with drug and alcohol addiction for most of his adult life.
Born on Dec. 10, 1965, Greg Giraldo seemed destined for greatness. Raised in Bayside, Queens by Colombian and Spanish parents, he grew up speaking fluent Spanish and English and took an interest in a wide array of subjects. But like many smart kids, Giraldo struggled to focus in school.
As Esquire detailed in a 2000 article, Giraldo’s teachers were concerned about his difficulty focusing and his fondness for cracking jokes — the tell-tale signs of a “problem child” in elementary school. However, Giraldo was a straight-A student, so his parents let the matter slide.
Giraldo went on to attend Regis High School in Manhattan, where his effortless string of A’s continued. During this time, he honed in on his comedic sensibilities, often quoting Saturday Night Live or doing impressions of Eddie Murphy. All the while, he was scribbling jokes that came to him into notebooks.
Giraldo was given an early acceptance into Columbia University — and Columbia proved to be no more difficult for him than high school. Career mentors encouraged him to apply to Harvard Law School, as he was good with his words and a competent arguer. The thought of being a lawyer had never crossed Giraldo’s mind before then, but he figured it would be a way to make a ton of money and make his parents proud.
In time, he would come to realize why, exactly, it had never crossed his mind.
From Harvard Lawyer To Comedian
Greg Giraldo never really fit in with the Harvard crowd. For a kid who grew up in Queens, the elite social atmosphere at the law school was daunting, and for the first time in his life, he found himself needing to buckle down and really put his all into his coursework.
He managed to pull a B-plus average and landed a summer job with a litigation firm in Manhattan. But the work there only further disillusioned him.
ZUMA Press, Inc./Alamy Stock PhotoGreg Giraldo at the Comedy Central Roast of Larry the Cable Guy.
This sentiment didn’t go away after he graduated. Even though he landed a job at Skadden Arps, one of the world’s most prestigious law firms, Giraldo felt unfulfilled, unmotivated, and defeated. Being a lawyer, it seemed, meant combing through documents, dealing with large companies that squabbled over trivial things.
“Before I quit, I was dying. I mean, I couldn’t do it,” he said in an interview with Psychology Today. “It wasn’t like I was a functioning professional and I just made the choice to throw it all away to pursue this crazy dream. I was incapable of being a lawyer… I was going to stop being a lawyer whether I wanted to or not.”
One day, overwhelmed with the mountain of papers on his desk, he picked up one of his old joke notebooks, and something clicked. The only thing he really wanted in life was to make people laugh, and he was going to pursue that even if it meant he would be a complete failure.
But it’s not easy to walk away from a lucrative and stable career to pursue something like stand-up. And even though it worked out for Giraldo, he would never quite shake the notion that he was a failure.
“I’m a total f—up, honestly,” he said. “The reality is I’m not this person with this driving ‘get it done’ attitude. I’m a complete f—up and I’ve f—ed up a lot of things in my life. I’m constantly tortured by a sense of failure. I feel like quitting all the time. I feel like hiding in drugs or alcohol. I feel like I’ve failed in terms of what my potential is.”
This feeling would persist throughout his life, even as his comedy career propelled him to greater and greater heights — and he would turn to drugs and alcohol to cope.
Greg Giraldo’s Battle With Addiction During His Comedy Career
Most comedians have to put in work for a decade or longer before a network offers them a sitcom — take Seinfeld or the ill-fated Mulaney, for example. But Greg Giraldo received an offer from ABC after just three years in the comedy circuit.
The show, Common Law, was loosely based on Giraldo’s time working in a law firm. Giraldo was the first person to admit the show wasn’t very good; it was canceled after only four episodes aired. But despite the show’s failure, Giraldo’s career didn’t suffer
ABCGreg Giraldo (center right) and the cast of Common Law.
Ultimately, Giraldo would become best known for his biting celebrity roasts on Comedy Central. Beloved by both audiences and his fellow comics, Giraldo had a real talent for insult humor.
Unfortunately, the more successful he became, the more he indulged in his vices. He would often drink heavily with fans at bars across the country while on tour, and accept drugs that were offered to him after gigs.
He knew the risks, but as fellow comedian Jesse Joyce told Vulture in a 2011 interview, “He could always out-argue his own mind, especially since he was a lawyer. He could easily come up with thirty reasons to stay sober tonight, or thirty reasons to get ripped drunk and ruin a bunch of things. He could talk himself into either.”
Joyce said he viewed Giraldo as something of an older brother and would often go to Giraldo for advice. But from watching Giraldo, he learned just as much about what not to do. Both comedians had decided to get sober around 2005, but for Giraldo, it didn’t stick.
“What’s so insidious about addiction is that it tricks you — and everyone around you — into thinking that this is the way it is for now, but that it’s gonna get better,” Joyce said. “Because we would have these periods of time where it was all fine and great, and I would get lulled into the idea that maybe this time it’ll stick… I don’t think Greg ever gave it enough time… I don’t think he ever gave it enough time to really reap the benefits of sobriety.”
The Tragic Death Of Greg Giraldo
Wikimedia CommonsGreg Giraldo died after performing a set at The Stress Factory.
The weekend Greg Giraldo died, he had just done a show at The Stress Factory, a venue he had performed at dozens of times before. Afterward, he hosted a party in his hotel room in East Brunswick, New Jersey, where he took too many prescription pills. He was eventually found unresponsive and rushed to the hospital.
Greg Giraldo died five days later, on Sept. 29, 2010. Just a year earlier, the NY Daily News reported, he had said in an interview that he had “conquered” his vices.
He was twice divorced, a father of three, and a bright comedian who wasn’t afraid to challenge people. But despite it all, he was also a struggling addict with a deep sense of self-hatred. And that combination proved to be deadly.