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Laughter's Gentle Soul: The Life of Robert Benchley

Laughter's Gentle Soul: The Life of Robert Benchley

by Billy Altman


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The definitive biography of Robert Benchley: humorist, actor, and leading man of the Algonquin Round Table.

Few American writers have ever achieved the widespread acclaim and multidimensional popularity attained by Robert Benchley (1889-1945) during the first half of this century. A charter member, along with close friends Dorothy Parker, Robert Sherwood, and Harold Ross, of the Notorious "Vicious Circle" that held court at the Algonquin Hotel in the Roaring Twenties, Benchley was many things to many people: a best-selling author of hilarious books chronicling the comic futility of the human condition, a sharp-witted theater critic whose reviews graced the pages of the original Life and The New Yorker for nearly two decades, and a much sought-after radio personality and feature film actor who starred in his own series of classic comedy shorts. In this sympathetic and witty biography, Billy Altman explores the man behind the mirth as he chronicles Benchley's journey from the glittering lights of Broadway and the dim ones in the rollicking speakeasies of New York during prohibition, to the infamous Garden of Allah apartments and the glamorously decadent Hollywood of the 1930s and 1940s.

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Product Details

ISBN-13: 9780393333350
Publisher: Norton, W. W. & Company, Inc.
Publication date: 04/17/1997
Pages: 384
Sales rank: 744,123
Product dimensions: 5.00(w) x 8.00(h) x (d)

About the Author

Billy Altman is an award-winning cultural journalist and critic whose work has appeared in such places as the New York Times, The New Yorker, Rolling Stone, and Esquire. He teaches in the Humanities Department of the School of Visual Arts in New York City.

Read an Excerpt



Lemon Drops Around Us Are



Born Isle of Wight, September 15, 1807. Shipped as cabin boy on the Florence J. Marble, 1815. Arrested for bigamy and murder in Port Said, 1817. Released, 1820. Wrote A Tale of Tivo Cities. Married Princess Anastacia of Portugal, 1831. Children: Prince Rupprecht and several little girls. Wrote Uncle Tom's Cabin, 1850. Editor of Godey's Lady's Book, 1851-56. Began Les Miserables, 1870, finished by Victor Hugo. Died 1871. Buried in Westminster Abbey.

— Autobiography by Robert Benchley, c. 1930

In fact, his origins were exactly the kind that one would expect of a son of late-1880s New England—Worcester, Massachusetts, to be precise, where, on September 15, 1889, Robert Charles Benchley was born. The first Benchley to arrive in America—one William Benchley of Merthyr Tydfil, Glamorgan, Wales—did so several years before the colonies rose up in revolt against the king of England, and by the 1840s William's descendants had moved the family from Smithfield, Rhode Island, to industrial Worcester, the "Heart of the Commonwealth," as the town's motto proclaimed. Henry Weatherly Benchley, William's great-grandson and Robert's grandfather, was a fairly well known local politician who, alter helping to found the Republican Party in the eastern portion of the United States, served first as a representative to the state senate and later, in the mid-1850s, as Massachusetts's lieutenant governor.

It's entirely possible that Henry Benchley could have gone even further in politics, but his sense of outrageat the way the South was conducting its social business led the widowed politician (his wife, Julia, had died in 1854) to leave his two sons, Charles and Julian, in the care of relatives and head off for Texas, where he eventually was arrested, tried, and jailed for operating a station on the underground railroad that was helping escaped slaves flee to the North. He died in Houston shortly after the end of the Civil War, but left enough of a mark on the area that, years later, a small community near Houston rose up bearing the name of Benchley, Texas.

Perhaps the fact that his father had been imprisoned by Confederates stimulated fourteen-year-old Charles Henry Benchley to lie about his age and in 1863 gain a place in the Massachusetts Voluntary Militia's 1st Battalion of Heavy Artillery in the War Between the States. Charlie distinguished himself enough to be promoted to corporal before the conclusion of the war, and he apparently enjoyed military service enough that, when he turned eighteen, he enlisted for a four-year tour of duty in the U.S. Navy. After he completed his Navy hitch, Charlie Benchley settled down to civilian life in Worcester in the early 1870s with his new bride, the former Maria Jane (Jennie) Moran, whose lineage on her mother's side, like Benchley's, dated back to Revolutionary stock, and whose father had come to America from Northern Ireland. In March 1876, the couple's first son, Edmund Nathaniel, was born, and the family remained a threesome for some thirteen years, until Jennie's unexpected second pregnancy resulted in the birth of baby Robert, a brown-haired, blue-eyed boy who was welcomed into the Benchley household with both surprise and delight-especially by Edmund, who gleefully carried his little brother all around the house and often rocked him to sleep in his arms before handling him over to Charlie, who, in turn, gave the child to Jennie for final inspection before bedtime (a practice which came to be known around the Benchley premises as "first, second, and third relief").

By all indications, it was Jennie, not Charlie, who was the dominant force in the family. Charlie Benchley was familiar to many residents of Worcester as the quiet and kindly mayor's clerk, and it was a sign of his efficient and accommodating nature that, although he was, like his father, a Republican, he stayed at his post in City Hall regardless of which party was in power, and was still on the job after thirty years and twelve different mayors at the time of his death in 1923. A short, stocky man with a bald head, thick mustache, and pince-nez glasses, Charlie also was the city's soldier's relief agent, which meant that his office was often filled with needy or down-on-their-luck ex-servicemen looking for assistance of some form or other, for it was common knowledge that Charlie Benchley would reach into his own pocket before allowing a fellow veteran to leave his office empty-handed.

Common knowledge, that is, until Jennie found out about her husband's philanthropy and started picking up Charlie's weekly paycheck herself. "His friends don't like me, hut his creditors love me," she was known to say, and proudly, too. That she sometimes laughed as she said it sheds at least some light on the complex personality of Mrs. Charles H. Benchley. Strong-minded to the point of intolerance and indefatigably strong-willed as well, Jennie Benchley kept Charlie on a weekly allowance that barely covered his carfare, thus enabling her not only to keep a good limit on his charitable donations, but also to discourage him from lingering downtown for post-workday rounds of drinks with friends at Worcester taverns. Charlie had begun to drink during his soldier days, but Jennie flatly refused even to acknowledge his predilection—in fact, the one time she discovered a pint of whiskey that Charlie had hidden in the house, the staunchly anti-alcohol Jennie ceremoniously poured it down the drain and later boasted to friends that "he didn't say a word about it." She was, however, a woman who often found it hard not to be rather amused by her own harsh manner and stern demeanor. After being run down by an ice truck once, she greeted well-wishers at the hospital she was taken to after the accident with a matter-of-fact. "They say I dented a fender." And while the Benchley home was literally dry, it did often sparkle with the wry, clipped humor that Charlie and Jennie Benchley and their two boys shared.

Edmund, in fact, was a bit of a prankster, as demonstrated by the time when little Robert, needing to learn a poem to recite in kindergarten, came to his older brother for guidance. The next day, when Robert returned home, he had clutched in his hand a terse note from his teacher to his parents concerning proper classroom behavior. The letter confused Charlie and Jennie—what on earth could the boy have done?—and they asked Robert if he could explain what had prompted it. The youngest Benchley confessed that the verse Edmund had taught him didn't seem to have pleased the teacher at all—a verse which, it turned out, went: "My mother-in-law hath lately died / For her my heart doth yearn / I know she's with the angels now / 'Cause she's too tough to burn." And before long, Robert was finding that he didn't have to rely on Edmund to let the family wit get him into trouble, as when he led a Sunday school hymn reading and substituted the word "lemon" for "mercy" in the phrase "mercy drops around us are falling." In both instances, neither Benchley boy was reprimanded by his parents; indeed, the lemon-drop incident was noteworthy more for Jennie's reaction to the reprimand received by Robert than for the actual "sacrilegious" jest, as Mrs. Benchley, displaying her customary protectiveness of her children, marched straight over to the teacher's house and berated the woman for not appropriately appreciating her son's attempt to "make the hymn a bit more cheerful."

Like most young boys, Robert eagerly counted the weekdays until the arrival of Friday, when, as he noted in a reminiscence many years later, the Benchley house filled with the comforting smells of a New England weekend.

We began getting whiffs as early as Friday evening, when the bread was "set" on the kitchen table and the beans "put to soak" nearby. The smell of the cold bread-dough when the napkins were lifted from the pans always meant "no school tomorrow," and was a preliminary to the "no school today" smells of Saturday....

On Saturday morning early these "no school today" smells began to permeate the kitchen, and, as the kitchen was the sole port of entry and exit during the morning's play outside, they became inextricably mixed up with not only cooking, but "duck on the rock," "Indian guide," and that informal scrimmaging which boys indulge in back yards, which goes by the name of either baseball or football according to the season of the year....

In New England, of course, the leit motif among the Saturday smells was the one of beans baking, but the bread and pies ran a close second.... Then, along about eleven-thirty, the noon dinner began to heat up.... it usually took the combined form of cabbage, turnips, beets and corned beef, all working together in one pot, with the potatoes, to make the "New England boiled dinner." That put a stop to any other smells that thought they were something earlier in the morning.

In 1894, the tall, good-looking Edmund graduated from high school, and through the influential help of Massachusetts Senator George Frisbie Hoar, he received an appointment to the West Point Military Academy. During the next few years, the family often took the long trip from Worcester across to New York State and over the Hudson River to visit Edmund, who, like most cadets at the time, rarely was granted leaves or furloughs. There they would stand and watch the afternoon marching drills, an event which the prideful Benchleys enjoyed even more after Edmund joined the color guard. Once Edmund's regiment, marching into the camp chapel, found itself distorting its neat files so as avoid trampling a little sailor-suited boy standing right in their path and waving to his embarrassed older brother. About the only negative aspect of the visits was that Robert, who was always fearful of loud noises, became terribly frightened by the sound of the sunset gun, and would usually run away and hide from everyone around the time of its firing.

In the spring of 1898, the Spanish-American War broke out, and Edmund Benchley's class was graduated ahead of schedule so that they could be sent into action in Cuba. After returning to Worcester for a few days in late April so he could properly say goodbye to his family and friends, the newly commissioned lieutenant went off to join the U.S. infantry stationed in Tampa, Florida. For a time, it appeared that Edmund's battalion would never have to take part in the actual fighting. "There is a feeling here that if we don't go before next week we won't go until fall, by which time it may well be over," he wrote to his parents in late May. "The officers here say it's the rashest foolishness sending us over there now and nobody would do it who knew anything about the matter. It doesn't seem to trouble anybody down here whether they go or not.... I never saw such a happy-go-lucky crowd.

The next week, however, the orders to sail did come, and before long Edmund was on a boat headed to Santiago, Cuba. "There was great disappointment on board when it was learned what our destination was," he wrote while still at sea near the end of June, "because everybody realizes the strategic value of Porto Rico and in case of the very probable termination of the war we would have something to show for our troubles and expense. One thing is certain—our stay in Santiago will be comparatively short.... We are to land at a place about thirty miles this side of Havana at Guantanamo; it is already in our possession and we will probably go into camp and sit there and wait for the enemy to surrender. I don't think it is the policy of our commanding officer to be very aggressive....

"Please don't worry if you don't hear from me once a week for awhile," he concluded. "Until we get definitely located, mail communication is likely to be rather irregular."

At the same time that Edmund was writing that letter, Jennie and Charlie were each sending off their own notes of parental concern and support. "I have come to the conclusion that it is not best to take too much stock in the papers," wrote Charlie on June 25. "They all, without any exception, exaggerate and magnify reports when the simple truth without any coloring is bad enough. Your mother nearly goes wild when she reads some of the reports. She is bound to pick out and brood over the discouraging ones and not consider the favorable ones in the least.... I saw by this morning's paper that the advance of Shafter's army had had a brush with the dagoes, and that ten were killed and fifty wounded, among them several officers....God grant that the fighting will not be severe by the time you are at the front." On June 28, Jennie wrote: "Sometimes I feel as if I couldn't breathe when I think of where you are. If only I could help you in some way...." Included with her letter were three pencil drawings by eight-year-old Robert, depicting a U.S. ship with a "Don't tread on me" flag flying from its mast, a politician making a speech while a cloud marked "peace" approached from above, and Uncle Sam rolling up his sleeve and making a fist, warning Spain to leave Cuba alone.

As it turned out, Edmund's letter from aboard ship was never mailed, and the young officer never received the last two letters his parents wrote him. On the Fourth of July, while the distinctive aroma of firecrackers filled the Benchleys' Worcester neighborhood, a newspaper reporter knocked at the door of Jennie and Charlie's home and delivered the grim news that their twenty-two-year-old son had been killed defending his country.

After landing in Cuba and setting up camp near Santiago, Edmund's company had marched into the battle of Fort San Juan at dawn on July 1, and the front line which he was a part of crossed the San Juan River under heavy fire from Spanish magazine guns, resulting in many casualties. At that point, according to the report filed by company commander Captain L. W. Kennon, "the brush was so thick that the other companies could not be seen, and the Colonel directed them to be brought up at once so that a full line of attack could be formed. He called Lieut. Benchley and directed him to recross the river—it had to be waded, being about waist deep—and carry orders to the battalion and company commanders to bring their troops forward at once. He started immediately on this important and dangerous duty and had succeeded in giving the orders to several of the commanders when he received a bullet through the heart, killing him instantly."

The terrible news of Edmund's death, coming as it did amid the ceaseless battlelike sounds and smells of Independence Day celebrations, was just too much for Jennie to bear. She began screaming uncontrollably, and it was several hours before her sister Lizzie, summoned from her nearby home by a distraught Charlie, was able to get her even slightly calmed down. When she finally appeared to have regained her senses, the first clear words she spoke were frighteningly blunt. "Why couldn't it have been Robert?" she cried—an outburst that so troubled those friends and relatives at her side that it was decided it would probably be best if Lizzie took Robert over to her house until his mother was back in her right mind again. (For the rest of his life, Robert would hate the sound of firecrackers—a grim reminder of the day he found out his brother was dead.)

It was a few days before Robert was able to return home. Somehow during that time, news of what Jennie Benchley had said got out among her neighbors, and it was quite a while before the gossip and behind-the-back chatter finally subsided. But whether it was primarily out of remorse over what she'd said, a need to repair the hurt she'd caused, or the instinctive protectiveness of a mother who'd already lost one child, Jennie Benchley soon was devoting much of her considerable energies to pampering Robert. She would allow no one to say a bad word about him or to him, encouraged his interest in drawing and music (he had his own mandolin and banjo by the time he was fourteen), and waited on him hand and, literally, foot; it wasn't until he was in high school that Jennie stopped tying his shoes for him. And while Jennie obsessively showered him with attention, Robert dealt with Edmund's death by trying to follow in his brother's footsteps, developing intensified interest in reading, drawing, dramatics, and charity work—hoping to be, for his mother's sake, as much like Edmund as possible.

Besides his mother, there was another woman whose relationship with Robert was significantly altered by Edmund's death. Lillian Duryea, who came from a wealthy starch-manufacturing family in Nyack, New York, frequently accompanied her two sisters on trips to West Point, where they provided company for young and eligible cadets at social affairs. It was there that she had met Edmund, and the two saw a great deal of each other throughout his stay at the academy. After Edmund was killed, Lillian announced to a somewhat stunned Jennie and Charlie Benchley that she and Edmund had been secretly engaged; moreover, she said, the two had planned to do a great many things for young Robert after they were married, and now that Edmund was gone, she felt it was up to her to keep her dead fiance's dreams alive by serving as Robert's friend and benefactress.

Although Jennie was a mother not especially tolerant of outside interference in the raising of a child, Lillian's connection to Edmund—as well as the fact that Lillian's headstrong personality was strikingly similar to her own—led Jennie to accept her. (In later years, each of the two women would confide to outside parties that the other was certifiably insane.) Soon Robert was being treated as something of a ward by the prosperous Duryeas. Every week he would dutifully sit down and write his mandatory letter to Lillian, detailing his progress at school and reporting on family news and items of local interest: and every year at the beginning of July, Robert would take the train to Nyack to satisfy Lillian's desire to have him at her side on the anniversary of Edmund's death—a date she observed by drawing all the curtains in the house and spending the entire twenty-four hours mourning in the dark. As Robert grew older, his visits to Nyack became more frequent, and the depression of the July commemoratives was counterbalanced by the gaiety of the Thanksgivings and Christmases he often spent as a guest of the Duryea family, as well as several New York vacations that Lillian took him on in which Robert got his first taste of the Broadway theater and his first glimpse of the hustle and bustle of New York City life.

Although Robert always noted in the diaries he began keeping during his adolescent years how much gratitude he felt toward Lillian and her family for the continued kindness they showed him, he seems to have regarded his part-time membership in high-society circles as simply an exciting extra, hut separate, part of what was to him a most happy and contented life as a middle-class Worcester teenager. That he felt this way was most likely a result of his mother's influence, since, from his very early years, the devoutly religious Jennie usually made a point not only of taking Robert to church with her but also of getting him to take part in the various Protestant charity activities that she was often engaged in. These regular reminders of the existence, and needs, of the poor helped instill in him both a sense of responsibility toward others and what his mother felt was a proper perspective on his own role in the world.

The neighborhood church played an important role in turn-of-the-century life in small-town American life, and it isn't surprising that Robert's diaries reveal a special regard for Sundays and their many church-related activities. A typical Sunday would begin with his taking part in morning services from his usual seat in the last row. From there it was on to his Sunday-school classes, the end of which would signal lunchtime, to be enjoyed either back at home or at his Aunt Lizzie's house, where he'd visit with his cousin Dot and sample the latest batch of wondrous cookies baked by Lizzie's Swedish cook. In late afternoon, he would return to church for the meeting of the Christian Endeavor group. With the other members of the religious youth organization he would sing hymns, recite short prayers, and then listen to the morally uplifting messages of visiting lecturers such as the crusading prohibitionist Carrie Nation, whose (as his diary described it) "red hot talk" Robert enthusiastically absorbed.

Sundays also were deemed the time for proper social interactions between the teenage boys and girls of Worcester, and the conclusion of Christian Endeavor gatherings was always marked by a town ritual in which the young men would ceremoniously request the honor of seeing that their favorite girl made it safely home. And for Robert Benchley that meant a leisurely walk through Worcester's friendly streets with one Gertrude Darling, whose family owned several wool-manufacturing mills and who had been Robert's classmate since third grade and his special friend almost as long as they'd known each other. As Gertrude later recalled to their son Nathaniel, her interest in Robert first came about for a variety of reasons, not the least of which was his virtually unsurpassed skill at making all the other kids laugh, either as the owner/operator of a neighborhood Punch and Judy puppet theater (the puppets had been given to Robert by Lillian Duryea shortly after Edmund's death) or through the amusing drawings that adorned all of his notebooks and school papers (and that he sometimes shyly left on Gertrude's desk as a present). Then there was the sympathy one always felt while watching him try to deal with even the simplest mechanical chore—for Robert, even something as seemingly uncomplicated as the sharpening of a pencil could turn into an arduous and exhausting battle from which he'd emerge only with point blunt and pride bruised.

At Worcester's South High, where he was president of both his freshman and junior class (Gertrude was his v.p. in those years), Robert distinguished himself in numerous areas—among other things, he managed the track team, served as treasurer for the school's dramatic club, and provided mandolin and banjo accompaniment for student minstrel shows and dances. Perhaps his most noteworthy achievement came the night during his sophomore year when, while acting as an extra for a traveling repertory company, he single-handedly stopped the show without uttering a single line of dialogue. The production was a medieval costume drama, and Robert's small role as a guard required that he wear a brass collar with long spikes sticking out. Halfway through the final act, while the action heated up onstage, he accidentally leaned against the backstage switch panel and blew out every fuse in the theater. That he wasn't electrocuted was to his friends and family a good reason to count their blessings; that the next day he announced his temporary retirement from professional theatrical work was for the show's producers a good reason to count theirs.

In early June 1907, while Robert was finishing his junior year, Lillian came to town to discuss Robert's future with Jennie and Charlie. Earlier that spring, in a letter to Robert, she had suggested that he allow her to lend him the money to go away to a prep school for his senior year, the idea being that he would then stand a better chance at gaining admission to one of New England's finer colleges. Robert, however, had dismissed the idea. "No doubt the living with a crowd of fellows would be a good thing," he wrote back to her, "but it is the preparation for the book side of college and not the social side that I ought to prepare for first, and there are few better places than Worcester for that. Our high schools stand as high as any preparatory schools in the region."

Within a few days after receiving his response, however, the determined Miss Duryea was sitting in the Benchleys' family room in Worcester pleading her case before a higher authority. While Robert sat by the door inside his bedroom upstairs straining to hear, Jennie and Lillian argued for better than an hour-Lillian extending her loan offer to include the cost of any four-year university Robert desired to attend, and the prideful Jennie insisting that, if it came to it, Robert would work his way through college. Eventually, the two women reached a compromise: Jennie would allow Lillian to be the one to determine the course of Robert's educational future, but whatever money she wound up spending would have to be considered an outright gift, and not a loan.

The prep school Lillian decided on for Robert was the Phillips Exeter Academy in Exeter, New Hampshire, and she took him there in mid-June to arrange for his taking the entrance examinations and to help him select a prospective room at one of the academy's residence halls. Although Robert had been having a great deal of difficulty with Latin in high school, he managed to pass Exeter's Latin exam after a few days of concentrated studying. This would have been the cause of great joy were it not for the fact that because of his turning all of his attention to that language, he failed the French test rather badly. Fortunately, though, Robert's principal at South High had sent in such a glowing reference ("I don't think we have ever received a recommendation which spoke so enthusiastically of a boy's character and ability," Exeter's assistant principal remarked in a letter to Lillian) that he was accepted anyway, and assigned a room in the Gilman House dormitory.

The summer of 1907 was a hectic one for Robert. At home in Worcester during the last two weeks of June, he saw a great deal of Gertrude, as the knowledge that he'd be going off to boarding school in the fall intensified what had blossomed from a childhood friendship into a serious relationship. It was a relationship that, during July in Nyack, Lillian apparently did her best to undermine by trying to kindle an affair between Robert and a friend of hers from Georgia named Lucy Hilton, whose family owned a summer home not far from the Duryeas. (Apparently, Lillian was holding on to the hope that Robert, though much younger than she, would somehow grow up to take Edmund's place by her side, and that a brief romance with some other girl would provide grounds for a breakup with Gertrude.) At the beginning of August, Robert returned home to spend several weeks playing his mandolin and reading at his usual voracious pace while Gertrude and her father (her mother had died when she was twelve) vacationed in Massachusetts. In mid-August, it was Jennie's turn to get some time alone with her son, as she took him for a week away to the seaside at Falmouth Heights; the very next week, Lillian again took over, treating Robert to a boat trip to Nova Scotia aboard the S.S. Rosalind. He got back to Worcester on September 8, leaving just enough time to pack his trunks and say goodbye to his family, and Gertrude, before heading off for Exeter.

If Lillian thought that attending a prestigious boarding school would cause Robert to aspire toward a more upscale lifestyle, she was mistaken. And, by the same token, if Jennie thought that being sent away to school would make Robert appreciatively homesick, she was also mistaken. Simply put, Robert thought boarding school was a pip. For the first time in his life, he was out from under the overly watchful eye of all female figures, and he found the rough-housing camaraderie of an all-boys school a new and enjoyable experience. His marks reflected this new touch of wildness. During his year at Exeter, Robert's grades were, at best, undistinguished (his highest average during the three semesters was a B-, and in his final term he received D's in three of his seven subjects). But he took part in a great variety of extracurricular activities, including the Mandolin Club, the Dramatic Club, the school yearbook, and the literary magazine, for which he drew comic illustrations. He demonstrated his independence when his English teacher told the class that for their senior paper they could tackle any topic that struck their fancy. While his fellow students went off to the library to delve into Swift, Milton, or Shakespeare, Robert took advantage of this opportunity for self-expression by paying several visits to the local undertaker. The result was a painstakingly researched, thoroughly detailed essay entitled "How to Embalm a Corpse," for which his instructor gave him an A—possibly for "astonished."

Robert's year at Exeter went swiftly, and as it did, the question of which college he should apply to loomed ever larger. For a brief time, he thought about seeking admission to Yale, but after several visits to the Harvard campus with Lillian, who would often arrange to meet Robert in Boston on Saturdays and spend the day with him, he set his sights there. In early May, Robert went over to Cambridge with Roger Hoar (son of the senator who had helped Edmund get his West Point appointment) and selected a room in a dormitory at Mount Auburn and Plympton streets that would be his if he passed Harvard's entrance tests. On June 15, a gangly Robert—standing just under six feet tall and weighing but 135 pounds—graduated from Exeter, with his parents and Lillian in attendance; one week later, after a cramming session to erase a year's worth of bad study habits, Robert went to Harvard to take the three-day battery of tests that composed the school's admissions exam. At the end of the month, he found out that he'd been accepted. Robert Benchley was going to be a Harvard man.

As had happened the previous summer, Lillian Duryea whisked Robert away for much of July and August. After the obligatory July observances were completed, Lillian and Robert left Nyack and traveled by boat to Nantucket Island, where they spent a week at a seaside inn in Siasconset celebrating Robert's acceptance to Harvard. In early August, Jennie again took him for a short stay at Falmouth, and then it was Lillian's turn once more, as she and Robert set off for a sightseeing trip through the Great Lakes and Canada's Thousand Islands region. Robert finally returned home to Worcester in early September, and he spent virtually all of the next few weeks by the side of a very subdued Gertrude Darling.

Tragedy had struck the Darling family back in June; the day before her graduation from South High, her father had suddenly died, and it turned out that he had been greatly in debt, resulting in the loss not only of the family's manufacturing mills but also of their house on May Street. In the spring, Gertrude had been admitted to Smith College. For a while she wasn't sure she would be able to go, but her older brother Albert offered to help her with money for her education, and her married sister Florence Reed offered her a room in her home to stay in when back from school. And when Robert reaffirmed his affection and love for her the day before she headed off to college, she was further reassured.

In a summer filled with great excitement and anticipation over his future, the only truly discordant note came in the form of an IOU that Lillian asked him to sign the last time he saw her in Nyack prior to leaving for Cambridge and collegiate life. The document, dated September 10, 1908, consisted of one lone sentence: "I hereby promise to pay to Lillian C. Duryea such amounts as I shall receive from her for the payment of college expenses." Besides making him affix his signature to the promissory note, Lillian made Robert agree verbally to two other conditions for the loan: first, that the terms of the repayment would be at the sole discretion of the lender; and second, that Robert promise that he would never tell his mother about the transaction.

Exactly what Lillian Duryea's motives were is unclear. Perhaps she had always intended that the money be a loan, and had only told Jennie that it would be a gift in order to end an argument she feared she'd otherwise lose. Or perhaps she felt that by solidifying his dependence on her, she could be assured that he would remain close to her, and could hope that as he matured into manhood, he might begin to see her in a romantic light. In any event, five days short of his nineteenth birthday, a confused but resigned Robert signed the IOU and vowed to keep the deal a secret. And whether the financing of it was ultimately going to be determined a gift or a loan, Robert Charles Benchley was going to be the first in his family's lineage to get an Ivy League education.

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