Jack McDougal Biography
Written by Nick Lingnofski
Note: This is the original bio Nick wrote for Jack. Many events and timing were changed in the creation of the timeline and the final play.

James McDougal III was born in Newark, New Jersey on September 4, 1951 during one of the worst thunderstorms the city had seen in years. He was the youngest of four children, and the only boy. His parents had had a few serious talks about whether or not three children was enough for them, but his father had always wanted a son to carry on the family names, first and last. Much to his father’s chagrin, however, his wife had no intention of calling her husband and son by the same name. She had grown up in a large Italian family with any number of brothers, uncles and cousins named Tony, which often led to a good amount of confusion and frustration. She vowed to prevent this in her own household. So although James III was on the birth certificate, from the moment he was born, his mother insisted upon calling him Jack (his middle name was Giacomo after her grandfather).
Jack’s family culture was an anomaly for the time and place. They were Catholic like many of his friends and neighbors, but Jack’s father was Irish Catholic and his mother was Italian Catholic. Where many of his friends had certain very specific religious habits and practices that their families took part in, for Jack religion seemed to just be an inherent environmental factor in his everyday life; a reason for a huge extended family meal or for something his mother was telling him to do.
His mother went to church every Sunday and insisted that Jack and his sisters attended as well, though his father never joined them. Jack often wondered why his father didn’t go to church, and sometimes asked his mother, but she would always just say that when he was old enough and a man he could decide whether or not to go to church and until then she didn’t want to hear another word.
Jack never really connected with the Catholic Church itself as a kid, but it was there that he first discovered his love of music. After church his mother would always have to help with some bake sale or fund drive, so Jack would hang out behind the church with the older kids. He’d sit there and watch as they played cards, smoked cigarettes, and played rock and roll on the little radio in the rectory window as loud as the nuns would let them. Jack would always be upset when his mother or one of his sisters would find him and tell him it was time to go home.
One of Jack’s other great loves was sports. To his father’s delight he was a naturally good athlete, usually able to pick up any sport and quickly be pretty competitive. He and a few of his friends would gather almost every day at an empty field near his house to play some sport or another. Jack’s favorite was baseball. Besides being a die-hard Giants fan like his father and listening to every game he could get on the radio, Jack loved to play the game. He loved standing at the plate (which was really a pan one of them had stolen from their mother’s kitchen) and tapping it with his bat, pretending to be Willie Mays and talking trash to the pitcher about how he couldn’t throw.
Jack’s father ran McDougal Drugs on the corner of Market and Ferry, where his grandfather had opened it shortly after World War I. It was a small store and often struggled to find enough customers to cover the family’s expenses, but James was so very proud to be carrying on the legacy of his father. He considered it to be the very symbol of his family’s American Dream, and would pontificate at great length about the grand days ahead when Jack would take over the reins and carry on the grand tradition his father had set before them. In fact, as soon as he was old enough to carry boxes and stack them on shelves, James put him to work. Jack often tried to count how many Saturday afternoon movies with his friend he had to miss because of having to work at his dad’s shop, but the number never seemed high enough to him to be right. He loved his father, but even from an early age, Jack knew that his future held something different for him. He would work quietly and let his father go on about retirement and the future of McDougal Drugs, not wanting to upset him, but knowing that he had no intention of ever taking over the store.
Jack also loved to read growing up. Each night after the family ate dinner, he would sit in the window at the top of the stairs and bury himself in a book. Since his parents weren’t big readers, they didn’t have a large book collection. He would read absolutely anything he could find around the house, often having to resort to reading his father’s newspaper or his mother’s ladies magazines. This gave him a level of exposure to the outside world uncommon for kids his age, which was always a matter of pride for James. He loved that he could sit at the dinner table and have a conversation with his 10 year-old about politics. James loved to talk about politics with anyone, but his favorite thing to do was to take Jack to work with him on Saturday mornings and listen to him rage on about those Washington assholes with all his cronies.
James was a conservative. He was an Ike man through and through. He had served under the General in Europe in WWII and had thought the country couldn’t be in better hands. Jack’s mother was more liberal, having worked with the poor for many years with her church. She and James would argue back and forth constantly about politics and what needed to be done to fix the country, their city, their street.
During the election of 1960, Jack would sit at the top of the stairs after he had been sent to bed and would listen to the radio broadcasting the debates from the other room. He’d hear snippets of the candidates and then he’d hear his father or mother chime in, which inevitably started an argument. When JFK won the race Jack’s mother bought a portrait of him and promptly hung it in the living room. It immediately became a running good-natured fight between his parents. At least once a week Jack’s father would take it down and hide it somewhere in the house, but it would always be back up by the time James got home from work the next day. That went on until November of 1963, after which the painting was never taken down again.
Jack was a naturally good student, though his grades could have been better. He didn’t see the value in the “work” that was so often required when he could just arrive at the answer with much less effort. He didn’t like to do homework, and would come up with absolutely amazing excuses for his teachers as to why it wasn’t completed. The more good-natured of his teachers even began to relish the stories he’d tell them, secretly impressed by his improvisational abilities. He always said that he thought his grades should be solely determined by his test scores, which he claimed showed his real ability to learn and absorb the information. He was always unusually good at taking tests, which of course fed the idea that he didn’t need to do homework. When faced with a load of impending school work, he would flash a smile and say something about how it seemed to him to be far more important to go out and experience life rather than spending time doing homework, which wouldn’t matter in ten years. And experience life he did. Or tied to anyway. Any time he wasn’t stuck at school or his dad’s drugstore he was out chasing girls, doing daredevil stunts, breaking bones. It was a difficult time for his mother.
Jack ended up graduating from high school with a solid B- average, which he considered to be more than acceptable. He was just excited to be moving on with his life. He spent the summer after graduation working at the drugstore and planning a backpacking trip through Europe. His father didn’t much care for the idea. With everything going on in the city at that point, he certainly didn’t think it was the right time for Jack to be leaving him high and dry. The riots had burnt down half the block that the store was on and the neighborhood was far from recovered, which made the store’s troubles compound. James said on several occasions that he felt it was the wrong time for such a trip, but after a few serious “listening sessions” with his wife he had relented. Jack would leave in the fall and see the world for a year solid. His parents had saved a small amount of money for him as a graduation present. His mother pressed it into his hands after graduation. He tried to give it back, and his mother said with a kiss and a light slap of his cheek that she absolutely would unless he used it to explore and expand his world.
Then, fourteen days before the date on his plane ticket to London Jack was drafted by the US military for service in Vietnam. His mother was devastated. She cried for days after he told her. James was much quieter on the subject. He, his father and his brothers had all served in the military and it seemed to make him proud that Jack would be too, though he held no love for the war in Vietnam or how it was being fought. He and Jack only spoke about it once, a few nights before Jack was due to leave. After dinner they sat on the front porch and James spoke very quietly about duty and country and what it means to have something back home to fight for. Jack sat listening numbly. He was terrified. Terrified and angry that this was suddenly his lot. He reported to basic training at Fort Bragg, North Carolina and touched down at Da Nang on October 1, 1969. It was his father’s birthday.
The US Military was trying to find its footing after the casualties suffered in the Tet Offensive. Opposition to the war was building in the US, and for the first time was not considered to be a “hippie” agenda. A week after Jack arrived in Vietnam he was assigned to a platoon whose task was to travel to areas that had just seen battle. They were to gather, identify and document as many of the remains of fallen US troops as they could. This was a difficult period for Jack. He found himself growing angrier and sadder as a person as time went by. He saw too many of his friends die unnecessarily. He began to withdraw. He started to have trouble sleeping. His buddies would try to cheer him up by talking to him about his family, or asking what beautiful girl he had waiting for him back home. The truth was he was beginning to feel like he didn’t have anyone or anything back home. The numerable girlfriends of his high school years were long gone and married to other boys who had paid better attention to them. When he would think of his family, the only things he could focus on were the impending expectations of his father. He began to lose weight and would become angry and volatile with anyone he came into contact with.
His commander, concerned that he would be unable to continue his duties, set up an exam with a military doctor. This doctor suggested to Jack that he might consider keeping a diary as a way to vent his true feelings rather than having to share his true thoughts with another person. At first he rejected the idea, but after being hospitalized for malnutrition Jack took his advice and began to write every day. He wrote about the war, about his feelings, about the men whose bodies he picked up each day. He found that it did help him. He was able to communicate in a way that he had not been capable of before. He felt that he could write his true feelings down on paper, and that they could speak for him more clearly than he could speak for himself.
In the fall of 1973 Jack was wounded by enemy fire and, after his recovery, was loaded onto a plane full of newly-released POWs bound for the States. Jack spent the flight talking to them about their stories and their families. They talked about what they would do when they got home; how their lives were ahead of them now that the war was behind. It was a day that Jack would always remember as one of the happiest of his life.
Jack arrived home on Thanksgiving Day, 1973. His mother had prepared a meal for the ages, and Jack felt like everyone he had ever known was there. His father was so proud of him, boasting to all his friends that his hero son had come home to stay. Jack wondered if James was lying to himself or to his friends by saying that. He hoped it was the latter. He was dreading the talk with his father enough without worrying that he was blindsiding him. The next day he and his parents sat on the front porch as he told them he was leaving. He had discovered that he had a gift, he told them. He told them he wanted to write. He wanted to write about people, about music, about everything. He left for New York two days later.
New York turned out to be both Heaven and Hell for Jack. When he arrived he began to make wonderful friends; friends who wanted to talk about art, about music, about drugs, about life. He also ran out of money quickly. He had a few friends who were writers for various newspapers and magazines, and he began to mine them for opportunities. He began to write as a freelancer, trying to get published anywhere he could. He’d sell one article out of ten, which wasn’t enough to live anywhere, let alone New York City.
In early 1975 Jack was reaching a crossroads. He was out of money, out of friends to lean on for a couch to sleep on, and facing the reality of having to go back to Newark. He had already had a few talks with his mother over the phone. He knew his father wanted him to come home to work at the drugstore. It was all he ever said to Jack when he came home now and then for Sunday dinners.
He was starting to pack his things in boxes when he got a phone call from his friend who worked as a junior reporter for The Atlantic. About a year earlier he and Jack had been talking at a party about the war, and Jack told him about the journals he kept and the stories he wrote about the soldiers coming home. The friend had asked to see the material and Jack had shared some samples with him. He had honestly forgotten all about it.
Jack’s friend told him that he had showed the pages to an editor at the magazine and they wanted Jack to excerpt his journal for the magazine. At first Jack was hesitant. He wasn’t sure he wanted to have his most personal thoughts and views on display to the world, but after some coaxing from his friend he met with the editor and inked a deal excerpting his writing as a 5-part serial for the magazine. It was the first taste of success that he had had since moving to New York. The stories were widely regarded as a new view from a talented new writer and Jack was hired on as a contributing reporter.
At a literary party in 1975, Jack was introduced to Mart Crowley. Crowley was a writer and playwright who had broken barriers a few years earlier with The Boys in the Band. He and Jack clicked instantly. As they began to spend time together, they became great friends. Jack loved the stories that Mart would tell and Mart loved Jack’s writing. He told Jack that he had a gift. He believed that Jack could write about people in a way that made them feel real. His writing made you feel as if you knew the person you were reading about. He introduced Jack to all the writers he knew, and suddenly Jack was living in a world filled with parties at Dominick Dunne’s penthouse and dinners with Tennessee Williams at the Four Seasons. Mart continued to tout Jack’s talent to anyone and everyone, and consequently Jack began to get more offers and requests for his writing.
In 1979 Jack received a Hillman Prize nomination for an article he wrote for the Atlantic on the Jonestown Massacre and the victims’ remaining families. He was offered a junior editor position with the Atlantic, and by the time he turned 30 he was one of the youngest and most-recognized members of the literary community of New York.