More Room in a Broken Heart: The True Adventures of Carly Simon

by Stephen Davis

  Carly: “I was a typical cheerleader, a very rah-rah high school girl, out to be the most popular. It was a very Ivy League trip…. But, in matters of both substance and style, I followed my sister Lucy. I emulated her life. I wanted to be her. I lived Lucy’s life all during high school. In fact, I have such a pure recall of the details of Lucy’s life that it still amazes her. I studied every detail. I copied her style, to the letter. I wore tight skirts and tight sweaters. When she wore her hair with a dip over her eyes like Veronica Lake did, I did too.

  “Basically, I was Lucy for a number of years. Then, when I was in the tenth grade, she went off to Bennington College, and she became a beatnik. Lucy had her ears pierced. Black leotards. She started wearing peasant blouses and blue jeans that were slightly cut off and frazzled at the edges. She grew her hair long and played the guitar. So, immediately, I became a beatnik too. I started a trend at my school: ethnic clothes and long braids down the back. Other girls started copying my look, and I seemed to be an innovator, but in reality I was still following Lucy.

  “The big change in my life happened when Lucy left Bennington and went to nursing school at Cornell. I somehow couldn’t see myself as a nurse. She had changed a lot in that phase, and I grew to love her even more, but not identify with her as much. At that point, finally, I became much more myself than ever.”

  Carly has said that her mother had her fitted for a contraceptive diaphragm when she was fifteen, which, if accurate, certainly says something about teenage Carly in the generally repressive sexual atmosphere of the time. It also speaks volumes about the eroticized atmosphere of the Simon household, in which Andrea was living more or less openly with Ronnie. Birth control was extremely avant-garde, and made Carly something of a sexual pioneer at her school, where rumors of heavy petting and “going all the way” could stain a girl’s reputation. But Carly Simon could give her classmates (if they had something going with a boyfriend) the name of the doctor who had fitted her diaphragm. Certainly Andrea Simon’s notion of preventing pregnancy, instead of ignoring the risk, was a decade ahead of its time, and also spoke to the sexual aspects of her own life.

  The Simon family’s animals were a big part of Carly’s childhood. Carly’s Scottish terrier, Laurie Brown, was very dear to her and inspired an early dog ditty, “Lorelei Brown.” Lucy’s dog, a terrier called Bascomb, suffered from seizures and inspired Lucy’s caring and maternal instincts. (The family accused Lucy of spoiling Bascomb.) Peter had a mutt called Besty, because her owner thought she was the best dog. Prowling the house were a variety of cats, including Guarder, Slinky, and Magellan. The comforting presence of these and other pets was one of the touchstones of Carly’s somewhat fraught adolescence.

  Odetta Holmes, Carly Simon’s idol, had released her first album, The Tin Angel, in 1954. A stolid black Alabama native (born in 1930) with a big guitar sound and a burnished female baritone voice, Odetta sang an almost operatic mix of blues songs, southern ballads, and old spirituals with the moral authority of an African American priestess. By 1958 she was a favorite in the Greenwich Village coffeehouses and folk clubs, and would soon be opening for superstar Harry Belafonte, and then headlining on the lucrative college concert circuit along with the Kingston Trio. (Bob Dylan later wrote that Odetta inspired him, in 1958, to switch from rock and roll to folk music.) Carly studied Odetta’s 1957 album, At the Gate of Horn, and realized that her own deep singing voice matched Odetta’s almost perfectly. This was a major inspiration, and Carly spent many nights sitting on her bed, the door closed, singing along to her idol’s hypnotic recordings. Andrea Simon said later that she used to eavesdrop outside Carly’s bedroom, tearful with joy as Carly sang along to Odetta’s records—in perfect harmony. (Carly’s high school yearbook for her senior year described her as “Riverdale’s answer to Odetta.”)

  Carly: “I remember, in those days, Lucy sitting on her bed with her guitar. She had a turntable on her bureau with an LP playing. It might’ve been Pete Seeger. It might have been Harry Belafonte. She was trying to imitate what the sounds were. She taught me the C-chord and the other two chords she knew—she was excited to share them with me—and then we switched the guitar back and forth… until I was finally on the subway down to Manny’s on 48th Street, with thirty five dollars, to buy a guitar of my own. We were young and malleable, and willing to get our fingers calloused and dirty.”

  Carly loved the way she and Lucy sounded when they sang together. She thought there was something ineffable in Lucy’s sweet soprano voice, a pitch and a sound that she described as “Scottish”—an ethereal presence that perfectly balanced the deeper tones of her own contralto. Carly had always loved to sing with her sisters, especially the three-part choir arrangements for standards such as “Ave Maria” that Joey was bringing home from her college’s music library. But there was something about the way she and Lucy sounded, alone, that moved Carly deeply. “The sheer excitement when we blended our voices—it just thrilled me,” Carly said later on.

  In 1959, Carly began taking guitar lessons at the Manhattan School of Music. She was also one of the best singers in her school, and a soloist in the chorus of the musical that Riverdale put on every spring. That year, it was George and Ira Gershwin’s 1930 Girl Crazy, featuring “I Got Rhythm” and “Embraceable You.” Soon she began dating the show’s male lead, senior Tim Ratner, a tall and handsome high school hero type. One day Carly brought Tim over to the house and casually showed him the photo portrait of George Gershwin—inscribed to her parents—in its silver frame in the Simons’ living room. (When Andrea Simon got a load of this new boyfriend, and the gleam in Carly’s eye, was probably when she hauled her daughter to the doctor for that diaphragm.) Soon Tim and Carly were the campus sweethearts of ’59, two star-quality kids strolling hand in hand, evidently in love with each other. They sang show tunes, sang doo-wop, Danny and the Juniors, the Contours, “Get a Job.” Late at night, on “study dates,” they locked themselves in the Simons’ book-stuffed attic and stayed up until two in the morning, snuggling, listening to Frank Sinatra mournfully croon “In the Wee Small Hours of the Morning.”

  Having fallen in love at sixteen, Carly found that her stammer had almost disappeared.

  In the summer of 1959, Tim often visited Carly in Stamford. He saw the whole scene: the increasingly dysfunctional father, the highly organized (but preoccupied) mother, the glorious older sisters, the funny twelve-year-old kid brother who published a mimeographed family newsletter, the Quaker Muffet Press. It seemed to Tim that Carly’s mother had a much younger boyfriend living on the property, which generated chagrin in his girlfriend, who didn’t want to talk about her family, as if she were ashamed or embarrassed by them. At summer’s end, Tim went off to Dartmouth. Carly, still in high school, wrote to him often, but eventually met someone else.

  The venerable Newport Folk Festival in the summer of 1959 was chugging along with its earnest mixture of topical songs, blues, bluegrass, and clog dancing when star folkie Bob Gibson brought out a pretty, dark-haired, barefoot eighteen-year-old singer to join him on a few ballads. The daughter of an academic who taught in Cambridge, Massachusetts, she specialized in old Appalachian songs and sang in a clarion soprano that made the Rhode Island festival’s microphones and speakers somewhat redundant. This was the national debut of Joan Baez.

  She had been singing, semi-regularly, at the Club 47 coffeehouse in Harvard Square, drawing an adoring crowd of students, Boston bohemians, and folk music fans. They queued down the street for blocks when local hero Joanie was on the bill. Her voice was described as angelic, and authentic. Joan Baez’s early career, after an enraptured reception by the folkies and beatniks at Newport ’59, would, in days to come, have a major impact on the careers of the two beautiful Simon Sisters.

  A DEATH IN THE FAMILY

  Carly Simon was in the audience when Harry Belafonte played at Carnegie Hall in April 1959. This was a double treat for her, because her idol Odetta opened the concert, earning a standing ovat
ion from Belafonte’s audience. These were the days when the civil rights movement began to heat up, with sit-ins and voter registration drives, especially in the South, with activists trying to change America from a segregated society to one that respected the equal rights of all its citizens. Harry Belafonte epitomized the new American Negro, deeply committed to the struggle against racial discrimination. His hyper-theatrical presentation of gentle calypsos and robust protest songs aimed to carry his (mostly white) audience beyond the confines of the venerable auditorium and into a communal spirit of a national struggle for change.

  Performing in his trademark V-cut silk shirt and tight black trousers, Belafonte divided the program into three acts: “Moods of the American Negro” (work songs and spirituals), “In the Caribbean” (“Day-O” exploded the house, followed by “Jamaica Farewell”), and “Around the World,” in which Belafonte sang in Hebrew, Creole, and Spanish. The New York Herald Tribune wrote, “Not even the presence of a small, rarely used orchestra or some garish lighting were able to deflect the instant rapport between [Belafonte] and his audience.”

  Carly: “I was a huge fan of his, and we used to go to Carnegie Hall whenever he was there. He was the first performer I ever saw who changed his shirt between songs. His neck was always open two or three buttons deep, and I thought he was very, very sexy. ‘Jamaica Farewell’ and ‘Day-O’ were my favorite songs. Harry made a big impression on me from the time I was twelve or thirteen.” (The subsequent recording, Belafonte at Carnegie Hall, was the first concert LP to be released in stereo, and immediately broke the sales records of Calypso, of three years earlier.)

  Autumn 1959. One morning Peter Simon was dressing for the seventh grade when his father told him to forget about school and come to work with him instead. Richard Simon informed Peter that, from now on, he would be running Simon and Schuster. “I just looked at my father,” Peter remembered. “He didn’t look well, and I was worried. I said something like ‘Well, Dad, I would certainly like to work for you some day, but I really think I should get to school.’” Dick stared at his son for a minute, saying nothing, swaying slightly. Andrea Simon came in and told Peter to go to school. Dick Simon took to his bed.

  He never returned to Simon and Schuster. He suffered a series of jolts to his heart and another stroke. He lived in his bathrobe. Much of the time he was silent, and seemed to suffer from catatonia. Sometime after Christmas, Andrea couldn’t take it anymore and sent him away to live in Stamford and be cared for by Aunt Jo. Later Dick Simon’s business partners formally separated him from the company in a complicated deal, aided by colleagues who (the family feels) took advantage of his enfeebled condition. At the age of sixty, Richard Simon found his illustrious career as a legendary American publisher tragically over.

  Carly was a junior at Riverdale as 1960 dawned, with change in the air. The Eisenhower years were over, and the political high ground was being claimed by the handsome young senator from Massachusetts, Jack Kennedy, who offered the country a new vigor and even a trace of glamour. Kennedy’s candidacy was espoused by the Simon family to the extent that Carly started calling her brother “P. T. Boat” after Senator Kennedy’s famous wartime torpedo-carrying attack ship.

  Young men were constant visitors to the imposing house on Grosvenor Avenue, especially when Lucy Simon was at home. One of her would-be suitors was an MIT student named Paul Sapounakis, who, one day in the spring of 1960, brought along his friend Nick Delbanco, a Harvard freshman and aspiring writer. “And you,” Paul told Nick, “can date the younger sister.”

  Nick Delbanco was from an old European Jewish family that had gotten out of Germany in time. Born in London, raised near Carly (in Westchester County), he was a young writer whose obvious talent was recognized early. He was already a fiction star at Harvard, his work appearing in the university’s literary publications. He was shorter than Carly, but handsome, funny, intense, knowledgeable, opinionated, sexy, passionate, older, and Ivy League—everything a girl could want.

  Soon Nick was a regular visitor. In March 1960 there was a party at Stamford to which he was invited. Dinner was served, and then the evening’s entertainment unfolded. Richard Simon, the august founder of the country’s greatest publishing house, was seated in an armchair, in pajamas and robe, alert but silent, his hands folded in his lap. Yet, Nick said, “He was still a magisterial presence in his own home. There was a definite aura there, even at that stage of his life.” The family then performed around the grand piano in the parlor, and there had obviously been rehearsals. The three Simon sisters offered show tunes, folk songs, arias, and Lucy’s song “Winkin’, Blinkin’ and Nod,” in various combinations, in an informal family revue. Carly expertly channeled Odetta on the folk ballad “John Henry.” She sang “Danny Boy” with the soul of a wistful Celtic bride. Uncle Peter Dean, strumming his ukulele, would crack the party up with ribald double entendres and extreme, eye-popping, cheek-bulging gurning. Peter Simon darted about documenting everything with his camera and flashbulbs. Observing the silent, invalided Richard Simon, a legend of the publishing industry, watching his beautiful daughters sing, Nick Delbanco felt that a courageous family was doing its best to carry on in the face of impending disaster.

  As for Carly, Nick got to know her on school vacations that spring. “She had the remnants of a stammer, and a forthright anxiety. She said that her family left her feeling insecure, unloved, and that her comic antics were a ploy to gain attention.” All she really wanted was for her beloved father to smile at her. Nicky wanted to be more than friends with Carly, but she was wary, preoccupied with high school and family issues, and kept him at a distance—for a while.

  The first time Nick saw Carly sing in public was early in the summer of 1960. Ronnie Klinzing had landed the male lead—“the Alfred Drake role”—in a Pocono resort summer stock production of Kiss Me, Kate. Joey Simon was Kate, and her sister Carly somehow conquered considerable stage fright and came out and sang a song. The production was way off Broadway, but the young cast did their best, and Carly Simon had made her public debut, in the verdant hills of eastern Pennsylvania.

  Dick Simon spent the summer at his estate in Stamford, often sleepless, in the care of his oldest friend, Aunt Jo. On the night of July 31, as the cicadas buzzed their mating song through the fruit trees in his orchards, he had a third and final heart attack and died at the age of sixty-one.

  Andrea Simon woke Carly the next morning with the devastating news, then drove away with Ronnie to collect Peter at his summer camp in New England to bring him home for the funeral. Carly was left alone in the house. She made it, numbly, to the bathroom, feeling sick. All the knocking on wood, for years, had come down to this. Her prayers had been in vain, and she felt abandoned by God. Carly decided to put on a proper show of mourning—“arrange my attitude,” she later said. In truth, she had been anticipating this awful moment for a long time. She later said she felt envious when her sister Lucy came home prostrate with grief. Lucy had called her father in Connecticut to say good night only a few hours before he died.

  Lucy later said that her grief for her father was tempered by her sense that her love and respect for him had been completely reciprocated. “My relationship with him was stable, and I felt very loved by him…. But Carly’s relationship with him was never totally established. His death made it impossible for her to complete this, and that’s where her anguish came from.” Years later Lucy would say that this unresolved bond between Carly and her father would play itself out in all her younger sister’s relationships with men.

  Dick Simon’s funeral was horrible, an ordeal for everyone, a vale of tears. Nick Delbanco showed up at the funeral, offering Carly a solid shoulder to cry on. “That’s the first time she took me seriously,” Nick remembered. “It was a very dark and complicated time for her.” Soon Nick and Carly were secreting themselves in the Simons’ attic. “That was the beginning of a real intimacy between us,” he says.

  Andrea Simon sold the valuable Stamford esta
te as soon as she could, to an exclusive, all-white private school that she insisted must integrate, as a condition of the sale.

  Peter Simon remembers that he and Carly mostly felt numb when their father died, and that his death really hit home when Andrea sold the Stamford house. “Neither of us could believe we were going to lose our country house in Connecticut. It was paradise, lost. We both cried and cried. That’s when it really sank in, to me and Carly at least, that our father had died.”

  CARLY CARES

  Fifty years after her father died, Carly revealed that she had lost some of her fortune, reportedly some millions of dollars, to a fraudulent financial adviser. This was front-page news during the spring of 2010, with the media invariably describing Carly as the heir to the Simon and Schuster fortune. The old family firm had changed hands several times since 1960, and was by 2010 a multibillion-dollar media empire. Carly, it was generally assumed, was very wealthy because she had inherited her father’s vast fortune.

  Carly took pains to deny that she was any kind of heiress. She issued a statement to the press: “The Simon family, the sisters and my brother and myself, are not the heirs to the Simon & Schuster fortune, because my father sold the publishing company years before he died. And so a lot of people get this wrong.” Any money that had been lost by her financial adviser, she explained, had been earned by her during her forty-year career. She pointed out that while of course she did receive some income from her father’s estate, the amount wasn’t exactly enriching. Carly told reporters that there had never been substantial trust funds for the Simon children, and that she received a small allowance from her mother until she was twenty-one. (Peter Simon estimates that he and his sisters each received legacies of about $80,000.)