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How does one do—notoriously pessimistic and humorously insightful essayist— David Rakoff’s work justice? How does one begin to fumble for the words to embody his literary range? Rakoff, who just passed away at the age of 47, wrote and spoke in a way that so remarkably reflected our uncertain collective reality—in his profundity, in his candidness, and in analogies so apt and relevant they surely required years of careful research into our human minutiae. In Rakoff’s essays, there’s deep pain, there’s sardonic humor, there’s desperate hatred, there’s even rhyme (sometimes). In reading Rakoff’s essays, you find yourself wondering over and over, how did he know? How did he so scrupulously pinpoint the intricacies of the human psyche? Below are just a few surface-scratching must-read hits from Rakoff’s prolific career:

In “The Waiting,” an essay which appeared last year in the New York Times Magazine, Rakoff describes the process of battling a long illness, while the greatest struggle at times seems resisting the urge to overanalyze his caregivers‘ words and demeanors as significant, as a predictor of outcomes. Rakoff writes, of the encouraging and empathetic feedback we are programmed to deliver to one another, “…as an anticipatory tool, it does not soften the blow, indeed it does the opposite. It leaves you exposed, like grabbing onto the trunk of a tree for support in a storm only to find the wood soaked through and punky and coming apart in your hands.” Undeniably, anyone who is human comprehends the feeling Rakoff captures, remembers the exact moment even, when plumbing the depths of desperation he loaded undue significance on the words of another. Anyone who is human recalls the moment in which he became—however fleetingly—superstitious.

In the essay “Stiff as a Board, Light as a Feather,” which Rakoff recited on This American Life earlier this year, he describes the experience of having a nerve in his left arm severed, causing him to have the occasional “gesture of someone who danced…which is very different,” he says, “from having been a dancer.” During the show, Rakoff elucidates the processes our bodies undergo, which we rarely question until they manifest as physical abnormalities. “There are some questions in life the very speaking of which are their own undoing,” he explains, for instance, “is this real?” It is the question, ultimately, which awakens him to the reality of his situation. Rakoff manages to take his ravaging sickness, and not only approach it with objectivity, but extrapolate to some wider, more philosophical meaning about the nature of consciousness. Whether or not he fully intends to, Rakoff can scarcely avoid offering us an outstretched hand, a gateway toward common identification. It’s never merely his experience, but what his tells us about all our own.

In 1996, on This American Life, Rakoff described his time spent dressed as Sigmund Freud in Barney’s department store Christmas window display in “Christmas Freud.” A version of the essay also appears in his collection, Fraud. “In the window I fantasize about starting an entire Christmas Freud movement,” says Rakoff, waxing on the complex relationship between psychoanalysis, spirituality and commerce across generations. “In department stores across America, people leave display window couches snifflingly and meaningfully whispering, ‘Thank you, Christmas Freud,’” he writes. Not afraid to go over the top, Rakoff undauntedly appropriated the situations which befell him with the mastery and dexterity of a world-class storyteller.

Rakoff writes in “All The Time We Have,” in his collection Half-Empty, of the death of his therapist of ten years (Rakoff was something of a self-professed therapy junkie over the years). The tribute is poignant and heart-wrenching, as he explores the complex relationship with a man who, in all his human vulnerability, ultimately required Rakoff’s approval just as badly. Rakoff writes so acutely of the push-and-pull struggle for approval, the hunger that reveals itself to be quite insatiable, the games we humans play, the waters we test, only to discover we are insatiable. Rakoff writes of this challenge we do not want to win because we fear its results: “this confirmation that you have triumphed again and managed to gull yet another mark, except this time it was the one person you’d hoped might be immune to your ever-creakier, puddle-shallow, sideshow-barker variation on “adorable,” even though you’d been launching this campaign weekly with single-minded concentration from day one.”

Finally, but by no means least or remotely comprehensively, Rakoff writes of attending a Tibetan Buddhist retreat led by Steven Seagal in an essay also appearing in Fraud. Portraying this outlandish, over-the-top New Age-y, self-help ritual, Rakoff is at his most poetic: “Twenty years ago we would have been readers of Robert Persig. Now we own well-thumbed copies of The Jew in the Lotus. We’ve done yoga. We’ve been lactose intolerant.” His fresh, concise commentary, which easily disavows the usual stereotypes—while marrying the expected with the uncanny and cynical—is so slick, so layered, there’s something new and potent to unearth on every read.

Rakoff published three books of essays and contributed widely to anthologies, newspapers and magazines. He was a regular on the radio show This American Life. All Rakoff’s contributions to This American Life can be found here.

iPad Snatch
A 33-year-old man told police that he was walking on the grounds of the Amsterdam Houses on Saturday morning when two men in their early twenties, one wielding a black handgun, approached him. The perp carrying the gun told the man, “Don’t say anything. Give me the iPad.” The man handed over his iPad, worth $799, and the two robbers darted into 217 W. 63rd St. in the housing complex.

Designer Thief
Two men entered the Sunglass Hut at Broadway and 79th Street Friday afternoon seeking designer shades. One of the employees in the store at the time, a 29-year-old woman, recognized the men from a previous crime. As the men approached, the employee and a co-worker told them to get out. But that didn’t dissuade them—the men began to grab multiple pairs of sunglasses from a rack near the door, snatching $1,520 worth of shades, all of them by Gucci and Prada. When the co-worker tried to take the glasses away from the culprits, one of the men pushed her away. The two men fled on foot out the door.

Forged Checks
Someone cloned a 68-year-old man’s checks from his checking account and used his personal information to transfer funds from one account to another, the man told police on Friday at 11 a.m. The forged checks totaled $26,000, and the man doesn’t know the people who deposited them.

Street Attack
A 45-year-old woman told police that a heavyset woman wearing a black do-rag hit her with an unknown object just after 4:30 a.m. on June 20, causing a small cut to her neck. The woman was removed to Roosevelt Hospital for treatment. Police said the woman was uncooperative and hostile, telling inconsistent stories.

Mystery Mace
As a 63-year-old Asian man walked on West 74th Street between Columbus and Amsterdam avenues on Friday evening, a 39-year-old man sprayed him with an unknown substance in a pink bottle, causing pain and swelling to his eye and the left side of his face. The older man was taken to Roosevelt Hospital and the perp was arrested that same day.

iPhone Grab
A 14-year-old boy was walking southbound on the east side of West End Avenue between West 77th and 78th streets on the evening of June 20 when two unknown men approached him. The taller of the men asked the boy, “Can I see your phone?” The men surrounded the boy, who told police that he was fearful for his safety. The boy handed his iPhone to one of the men and continued walking southbound without looking back. He didn’t notice in which direction the robbers fled.

Picture of a Crime
When a Japanese tourist paused to take photos on the southeast corner of Central Park West and West 66th Street on the evening of June 17, he didn’t realize that placing his black Tumi bag on the ground next to him would cause a problem. As he snapped a shot, someone picked up his bag, containing a $325 Gucci Wallet, $800 in cash, Japanese currency and a Japanese passport, and immediately fled.

By Megan Bungeroth

Wayward Waitress?
After his online bank statement informed him that someone had purchased a British Airways flight for $1,602.76 using his account, a local man came to the precinct to report some other suspicious activity. At the end of January, he received a call from Ticketmaster telling him that there had been an attempt to purchase tickets to a sporting event using his bank card, which he denied and reported to Ticketmaster’s fraud department. However, he didn’t call the police at the time. With the unplanned vacation tip-off, the man began to suspect that he was the victim of identity theft at the hands of a waitress. He remembered dining at a French restaurant months ago, and that the unknown waitress had held his New York state driver’s license and his Wells Fargo Visa card for over two hours—plenty of time to copy down the relevant info and start planning a stolen getaway.

Failed Stick-Up
On Monday at 3:15 p.m., a man walked into a Citibank branch on Columbus Avenue and approached a teller window. He passed a note demanding money, muttering “Hurry” as the teller gathered the cash together, but the would-be thief apparently got too impatient and suddenly left on foot, without the loot. Police are still looking for the suspect.

Theater Theft
A mother and her young son went to see a movie at the Loew’s theater on Broadway last Thursday, and mom plopped her purse on the empty seat next to her. She was distracted by her squirmy son and didn’t glance at the bag for about an hour; when she did, it was gone, as were her $200 iPhone, $99 sunglasses, $100 bag of makeup and all her money and credit cards.
Rent Switcheroo
A 23-year-old college student wanted to sublet his apartment and listed it as available for $2,300 a month on his school’s website. A woman contacted him, interested in renting the apartment. Then she “accidentally” sent a check for $3,650, she informed the student, and asked him to wire back the difference to her. He wired her $2,400 via Western Union, and when her check arrived via FedEx the next day, it bounced. The victim told police that he has no way to get back in touch with the scammer, but suspects that she’s in Turkey.

Missing Inventory
An employee at a Sprint store on Broadway was conducting inventory last week when he realized that four HTC Evo phones, worth $400 each, were missing and unaccounted for. When the store checked its security footage, they noticed a man opening a drawer and lifting the phones right out while several possible accomplices distracted employees.

Running Start
A student was standing on the corner outside Fordham University at West 60th Street and Columbus Avenue when a man ran past him and snatched his $700 iPhone right out of his hands. The perp was out of sight before the victim could try to pursue him.

Dodge Rip-Off
A visitor from New Jersey parked her 2007 Dodge Nitro on West 85th Street on Wednesday afternoon, and when she returned a short time later, saw the rear door hanging open. She could not remember if she had locked the car, but she certainly noticed that her $1,000 laptop, computer bag, tools and Kodak camera had been stolen.

A former custodian at an Upper West Side high school pled guilty for defrauding the city of more than $100,000.

District Attorney Cyrus Vance announced Philip Portelli, a 33-year-old former custodian at Edward A. Reynolds West Side High School, pled guilty to running a “no-show job scheme.”

Portelli, who lives on 355 E. 88th St. and First Avenue, submitted time sheets to the Department of Education on behalf of a friend that did not work at the school, located on 140 W. 102nd St. and Amsterdam Avenue. The time sheets totaled nearly $105,000. The Department of Education recouped the loss.

Portelli was charged with a count of grand larceny in the third degree.

Outgoing Manhattan District Attorney Robert Morgenthau said the bagel magnate stole withholding taxes—taxes taken out of employees’ paychecks—and evaded unemployment insurance tax. The tax charges are in connection with H+H Bagels’ retail store at 2239 Broadway and West 80th Street, as well as the company’s wholesale operation.

The district attorney’s investigation alleges that Toro collected but failed to pay $369,318 in payroll taxes. Toro is also accused of creating six shell organizations to get a lower unemployment insurance tax rate by moving a large number of workers between these fake companies. He is charged on two counts of violating labor law.

On May 29, two H+H Bagels stores, including the famed Broadway location, closed for three hours when the state department of taxation seized the business. H+H Bagels was allowed to reopen after paying the liability.

Toro was arraigned in State Supreme Court Nov. 18 and pled not guilty. He surrendered his passport and was released on his own recognizance. He is due back in court Dec. 4.

As of Nov. 23, the Broadway outpost was still open.

• For how many years do I need to keep tax returns? You should keep your tax returns from 2008, 2007, 2006 and 2005. The IRS will usually only go back three years, and New York State will go back four years. If you practice fraud, they can go back seven years. Fraud entails understating your income by more than 25 percent, or taking fake deductions of more than 25 percent. The State of New York does not have any limitations. After eight years, the IRS destroys their microfilm records. You cannot get a copy of your tax return after eight years.

• What records should I keep? If you file a long form claiming medical expenses, taxes paid, contributions, etc., save all of these checks and records. If you prepared a short form tax filing, you do not need to keep anything except your income records. Shred your rent receipts, utility bills and bank statements. Make room at home. You should save records on any stocks that you purchased, but have not yet sold. When you sell a stock, you must provide the date of purchase and the stock’s cost, and the date of the sale and selling price. Not reporting the sale of stock on your tax return is one of the biggest problems taxpayers face. Some people say I lost money on the trade, so why do I have to report the loss? All sales of securities are directly reported to the IRS. Your tax return must match their records.

Also, keep records on all traditional, non-deductible and Roth retirement accounts that you opened and funded during your working years. When you reach age 70-and-a-half, you are required to make minimum annual distributions from your retirement accounts. Please remember “minimum” does not mean you have to take it all out at one time.

• Long-term care insurance premiums: These are deductible as a medical expense on your federal tax return, and New York State gives you a 70 percent tax credit on their return.

• Recovery rebate credit: If you did not file a 2007 tax return, you may still qualify for the maximum economic stimulus payment in 2008. Make sure you file.

• Other deductions: If you pay little or no New York State tax annually, and you complete a long form federal tax filing, you could be entitled to claim a sales tax deduction or schedule A for sales taxes paid.

• Surviving spouse’s home sale exclusion: A surviving spouse who sells a house or apartment that they live in as their home after 2007 can claim the $500,000 exclusion on a sale within two years after the death of the spouse. This is provided that the $500,000 exclusion was theirs legally before the first spouse died.
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Gary E. Reska offers individual and business taxes, and complete bookkeeping and business forms service. Contact him at 212-249-2525 or gary@garyreskatax.com.