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Adapted from "Who's Killing the Great Lawyers of Harvard?" — originally published in the August 2000 issue

Kids who pull straight A's in grade school don't often scare teachers. But for all his smarts, Greg Giraldo couldn't focus in fifth grade, and it disturbed those in charge. The kid from Queens daydreamed about funny people, guys who made other guys laugh. How thrilling to live at a time when John Belushi roamed the earth! How glorious to be Mad magazine artist Don Martin and to invent words like thwap and glork! Watch the face of a kid in love with laughter; it's not a face that soothes the schoolteacher's soul.

Mr. and Mrs. Giraldo were summoned to school and asked, Is something wrong at home? Is something troubling Greg? Nothing that we know of, the parents replied. And they returned home and asked Greg if there was something wrong. Not that I know of, he replied, and he returned to recording funny little thoughts in the journals he kept. Mom and Dad couldn't protest much; Greg was a perfect student, the kind who might fulfill an immigrant parent's dream that he become a doctor or a lawyer, or, better yet, an Ivy League doctor or lawyer. Or, best yet, a Harvard doctor or lawyer.

The highest compliment ever paid to Greg Giraldo came when his pals in Queens refused to believe he'd been admitted to Manhattan's prestigious Regis High School. We never knew you had a brain, they told their friend. We thought you were a fucking retard.

Once inside, Greg tore up the place. Shunning nerdiness, he pulled A's without losing his affection for the word fuck or his taste for the off-color joke. He read great literature, not because he was an egghead, but because Swift and Shakespeare were damn funny guys who knew how to construct a joke. His classmates dug his memory for Saturday Night Live dialogue, and they'll still tell you that his Eddie Murphy impressions were scary good. The Jesuits--great teachers, to Greg's mind--appreciated passion in a student, whatever the passion, so no one panicked about the joke-and-gag notebooks Greg continued to assemble. In a school where the graduates matriculated to Ivy League colleges as a matter of routine, Greg was getting Columbia University to commit to him early.

And Columbia would be great. Greg would live downtown, keep his friends, and enjoy the kind of life that comes with having the kind of non-dickwad, covertly cool brain that sneaks up on people.

Columbia proved to be no sweat; he'd already read half the books assigned to English majors. Around junior year, he began to hear what many verbally talented college kids hear from well-meaning mentors: Go to law school if you're good with words and like to argue. Sounds good, Greg figured. And if I can get into Harvard Law School, I'll be rich to boot. Without studying a lick for the entrance exam, he scored in the 99th percentile, deity territory to those who cared about such things, which he didn't. He got the thick envelope from Harvard, and while he still had no clue what lawyers did for a living, he figured it was time to go out and make his parents proud.

Mr. and Mrs. Giraldo delivered Greg to Cambridge full of hopes and dreams, but without the right clothes. Harvard Law School was throwing a get-acquainted cocktail party the first night, and the Queens kid had never had occasion to dress for splendor. Greg scoured the town for what he assumed to be the staple of high-fashion evening wear--the blue blazer. That he purchased one with zippers was not to embarrass him for a full four hours, since the party didn't start until eight.

The law-school social scene never stopped being bizarre to him. HLS would plan boat rides or nickel-beer Thursdays or L. A. Law Night at the pub, events that were supposed to break the ice but that, to Greg, just sucked indescribably--"in the deepest way," he'd tell buddies back home. Everyone was so used to being perfect, so sheltered, that they hadn't a clue about the real world, it seemed.

The legal minutiae Greg expected to be de rigueur at Harvard Law School never materialized. Professors concerned themselves instead with sweeping issues of grand importance, about the role of society and the responsibility of citizens, and it thrilled Greg. Never the "gunner" type to shoot his hand up in class, he lived in the back rows during the first weeks of school, marveling at his classmates' intellectual might. There were no chinks in the armor here. A student might sit for six weeks without uttering a peep, praying to be ignored. Then the professor would pick that student's name at random from the seating chart, whereupon that student would launch into a multilayered explanation of the difference between Kant's and Spinoza's conceptions of free will. Greg had long ago mastered the art of skating through school on brainpower alone. But this wasn't school. Here, among titans, he decided to commit 100 percent to his studies. Any less and he'd drown.

Greg pulled a B-plus average the first year, then landed a sweet summer gig with a small Manhattan litigation firm. The little work he was assigned worried him, though. The law wasn't majestic in these offices the way it was at Harvard Law School. Cases seemed petty, one corporation trying to fuck another corporation. Greg chalked up his reaction to immaturity. He'd never had to buckle down--things had always come easy. Snap out of it and grow up, he'd tell himself. It's time to become an adult. Not everything needs to be fun.

Greg pep-talked himself back to Harvard Law School. Just grow up and you'll want to be an attorney, he repeated as if it were a mantra, but his soul wasn't buying it. He remembered the weariness on the faces of the lawyers who took him to lunch to recruit him.

Back in Cambridge, Greg bought prepackaged outlines to cram for finals in classes he wasn't bothering to attend. Money became a primary motivator. The firms paid a shitload of money, and he intended to keep the promise he'd made to his parents when he was seven--a restaurant for his father, shiny dresses for his mother.

Second summer--another fancy Manhattan firm. His duties: Attend Mets games, eat four-star lunches, collect $1,750 weekly paychecks. As in the previous summer, his few real assignments struck him as meaningless. Every day, Greg toyed with the idea of dropping out. Every time, his conclusion was the same: Grow the hell up. Become an adult. You'll love this stuff.

Standing in line to register for third-year classes, Greg found a buddy and compared summer notes. Listen to this, Greg said. A recruiter tried to sell me on his firm. You know what he uses as his closer, the thing to seal the deal? He tells me, "We really encourage associates to have a life here. I'm taking a tax class at NYU and I can leave work at 7:30 p.m. two days a week, and no one says boo!" Greg and his buddy traded jokes about the kind of guy who says, "no one says boo," but neither of them was laughing much inside. Third year was a cakewalk, then Greg took a job even most Harvard students couldn't get, with Manhattan's Skadden Arps, one of the most prestigious, highest-paying law firms in the world. I'm going to grow up there, Greg told himself. I'm going to give it everything I've got.

New suit, new attitude. Greg showed up at Skadden Arps determined to grow up and knock 'em dead. Then they handed him two hundred documents and told him to close a real estate deal. He studied the documents, the fine print, the hereins and the wherefores. Each was uniquely necessary to the deal, and each looked so goddamned identical that he wondered if God was playing a cruel joke on him. He was earning $87,000 a year as a glorified clerk. No one at Harvard Law School during those discussions on the nature of man and society had bothered to mention that you needed to be a clerk to do this job.

Greg brought his improved attitude to closings but always managed to forget or misplace critical documents. One partner--he'll never forget the look she gave him--asked, "What are you thinking? Who are you?" He left that closing crushed, defeated in a way he'd never known. This work was doable, yet he couldn't get himself to care about monolithic companies trying to fuck each other for another dollar a square foot. His dreams to get rich and provide for his parents, to make them proud, were going to shit. The only decent thing in his life, he thought, was the comedy writing he'd been scribbling in notebooks--fanciful, escapist stuff he thought might work on Saturday Night Live or even onstage. But Skadden Arps didn't pay for nonsense like that.

Snowed under a mountain of documents one evening at work, Greg reached into his bottom desk drawer and found that notebook of jokes. This is insane, he thought, paging through Back Stage for the listing of clubs that sponsored open-mike nights. Later that night, and nights after, people laughed at material he'd written, which Greg figured to be about the greatest feeling in the world. He became acquainted with an important moment, the moment that happens when you're doing what you're meant to be doing. Not long after, he quit the law. Once people laugh at your jokes, he thought, there's no doing law.

Greg moved back into his parents' home and took odd jobs to support his comedy. He helped a director move offices once, even agreed to polish the guy's trophies. Sitting on the ground with a pail of borax and a bunch of rags, Greg thought to himself, I graduated from Harvard Law School. What am I doing with a pail of borax? Then he thought about those piles of legal documents, and he made those trophies shine.

A comedian like Ray Romano or Jerry Seinfeld works ten, fifteen years before he gets a shot at a sitcom, and then only if he's lucky. Greg had been doing stand-up for three years when ABC offered him a prime-time show. The program, Common Law, would star Greg as a hippie-ish Harvard lawyer who, despite being trapped in a major law firm, needed to be true to himself. The network promoted the hell out of the show, plastered Greg's mug on every McDonald's place mat in the country. Greg is correct when he says that the show sucked. The acting, the writing, Greg's hair--it all sucked. ABC canceled Common Law after four episodes.

Saturday night, just after the millennium, Manhattan's sold-out Comedy Cellar. Greg Giraldo is featured this evening. "Direct from his own ABC sitcom, Politically Incorrect, and NBC's Later show, please put your hands together for Greg Giraldo!" Lots of applause, then Greg launches into his gay-bodybuilder routine. Later, near the end of his set, he ponders why courts recently awarded a man millions of dollars for scalding his genitals in a defective shower. "That's a hell of a way to test the water," he says, thrusting his pelvis into an imaginary stream of boiling shower water. The crowd eats it up and stands to cheer for Greg, who will be playing Milwaukee next week, if you happen to be there.

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