I knew then there was an adversary within me trying to take over my body and mind. I didn’t know it was Lyme disease, of course, nor did I realize how much more pain and torment it would put me through, but I knew I had to endure it to find out why I was given this path. I know this may sound crazy, but that night it was as clear to me as water in a mountain creek. I would come to find there was nothing crazy about it. The insight was real and it would ultimately save me: You have to go through Lyme to get through Lyme.

  By the summer of 2001, my uncle Billy was dying of brain cancer. Besides being a musician, Billy was a landscaper and for a while planted the flowers and greenery on the roofs of many Park Avenue apartment buildings. It was thought that the pesticides that he used caused his illness. At the end he was in Los Angeles, and along with my whole family I went out to California to stay with him. He had just undergone his fourth operation, this one performed by a prominent surgeon whom Quincy Jones had recommended to my dad. The best in the world, however, couldn’t save Billy.

  Though Billy was still very ill, I returned to New York in the beginning of September for the start of school. On the morning of September 11, staff took us into the auditorium for an assembly. They announced that a plane had flown into the World Trade Center and some of the kids’ parents had called to take them out of class. I went back to my Spanish class, where the principal told me my father had called and he wanted me to come home.

  My dad had become quite close friends with Sarah Ferguson, the Duchess of York. I love Sarah Ferguson and I secretly wanted her to be my mommy (don’t tell my mother). Once I spent a night at her house in York. That morning of September 11 she’d been interviewed on the Today show by Matt Lauer about her book, Little Red. She was scheduled to leave the show for an early meeting at a charity she was involved in but was running late. The charity’s office space was on the 101st floor of one of the World Trade Center towers. The scheduling glitch saved her life.

  My dad and I drove up to Connecticut and Sarah followed. New York was in shambles. Even though they were separated, my mother and father lived across the street from one another in Connecticut. My parents were and still are very close friends. My dad even had the same white fence my mom had in front of Denbigh Farm installed in front of his house so the kids would think of his place like an extension of home. We all spent the evening together at Denbigh Farm. Sarah slept in my bedroom at my dad’s house. When I showed her to my room, I told her to wait in the hallway because I needed to check something.

  At this point, I had picked up the weed again. Unfortunately the chanting and third-eye tapping was not helping my physical pain as much as I hoped. Pot was more instant and easy (and fun) anyhow! I wanted to make sure I didn’t have any marijuana paraphernalia lying around my bathroom or anywhere else. When I finally let her in, she noticed a photo of herself, her two daughters, Beatrice and Eugenie, and me together on a vacation we went on one summer. Sarah thought I had gone into my room to put it there so she would feel special. I hadn’t; the photo was one of my favorites that I kept around all the time. But I think what she believed made her feel cozy and welcomed, so there was no use telling the truth. She made me feel so comfortable when she had me as a guest in her home in England, and I wanted to do the same.

  Four days after 9/11, Billy went into a coma in Elmira. He had returned to live with Nonnie after the surgery in Los Angeles to recover. We visited him and when I held his hand he looked straight into my eyes. I said, “Uncle Billy, I’m going to do everything in my life that you loved to do in yours. And you don’t have to be in pain anymore.” He squeezed my hand. That night he closed his eyes and never opened them again. Two days later they took him off life support.

  After Billy died, I started to paint again. I hadn’t painted since attending Sacred Heart. Painting became my therapy. The pressure of everything then—Billy dying, my health, my parents’ divorce, and 9/11—was just too intense. I drilled three huge canvases together. I ripped photographs out of magazines, a lot of graphic images, a lot of images of targets, I guess because that’s the way we New Yorkers felt then. I also ended up gluing a spatula on the canvas—don’t ask me why, but it was probably some cryptic way of saying I wanted to scrape out all the icky energy in me and around New York. It was a pure stream of intuitive subconscious. I began to hear Uncle Billy’s voice singing “Alexandria” to me.

  My creativity in September 2001 was not planned or orchestrated. The only way I knew how to identify my emotions was through art because I had been so used to repressing them throughout the years. My art always held a deeper meaning, and I had things I was really trying to say. So I just dove right in and let it all come out. I would come home from school, throw on some sweats and a T-shirt, throw down a tarp, and just go for it. Looking back at the pieces I made back then, I can easily identify what I was going through as if I were reading journal entries.

  I started wearing my hair up in a beanie when I painted because Peggy Lipton wore it that way. Peggy is the mother of my friend Kidada Jones, and one day we went to visit Peggy in the hotel where she was staying. I remember she looked so chic, so beautiful. Her hair was gathered up in a beanie. Peggy is a very centered and wise woman. We talked about astrology; she was spiritual, open, and soft, a very interesting person. And she listened to what I had to say. I remember thinking that I wanted to be like her when I grew up. She inspired me to be comfortable in my skin and to take care of my actual skin because I’ve got only one body!

  I painted a lot of American flags then, but I’d make them very distorted. In one of the pieces I put strips of newspapers in the white stripes of the flag, and I wrote a long poem on the newspapers. It’s funny how one thing leads to another. The poem opened me to writing. It was then I began to journal again. I didn’t keep the journals every day but I began to enjoy writing little observances, short stories, and poems. I took a creative writing class with Ms. Sclan.

  It’s no coincidence, perhaps, that my spiritual awakening in Central Park coincided with an awakening of artistic urges. They both come through the same channel, I believe, and they came fast and furious. It was at this time that I began to walk the city with a video camera around my neck, and a few years later a Polaroid camera, taking pictures of things that I wanted to remember but was worried I’d forget. I put them on the wall in my first apartment. Those Polaroids became a kaleidoscope of expression and montage of my life. It was wonderful: I was an open vessel and the universe was pulsing through me.

  It was around this time, my junior year in high school, that Dad told me about a screenplay our family friend Mary Pat had given him. Some years before, Mary Pat had written a book called Proudly We Served, about the African-American sailors aboard the USS Mason who fought German U-boats during World War II. Mary was (and is) a Northern Ireland historian, and the USS Mason was docked there during the war. “I’ve got a screenplay for you to read,” my father said in the car as he drove me to Greenwich. “It’s really cool, and I think it would be something you’d like.” He was very excited about the project and wanted my opinion of it.

  My dad always had a lot of faith in me when it came to my creativity. He trusted my taste in clothing and always brought me in to look at the designs of his new collections. He trusted me to make the right decisions about classes, which friends to hang around with, and how I wanted to spend my free time. He trusted me to navigate my own life.

  On one hand, maybe Dad trusted me too much. I was his teenage daughter and yet he treated me almost like a very close friend. He loved me. That goes without question. He just perhaps let me grow up a little too quickly.

  On the other hand, being my dad’s daughter, and having my dad as a father, allowed me incredible adult opportunities that normal teenagers wouldn’t even dream of, and one of those opportunities came with Mary Pat’s screenplay.

  I was flooded with ideas when I read the screenplay, and I wrote my comments right on the pages. My dad read them and thought they were helpful. I met with Mary Pat; we sat at the dining room table in our apartment in New York surrounded by all of my paintings. She explained how she got involved in the story, and how she knew all of the sailors, who were by then in their eighties.

  My dad was passionate about the screenplay and said he’d finance it. I remember him telling Mary Pat, “We need heroes now.” New York City was still an open wound from 9/11 and patriotic fever ran high. When Mary Pat and I met, I asked if she’d direct it, even though she didn’t have experience as film director, and Mary Pat asked me to be the producer, even though I was sixteen years old. We figured that even though we didn’t have experience, the story needed to be told.

  You may be thinking, Are you fucking kidding me? How many sixteen-year-olds get such an opportunity? But I lived in a house of workaholics and if you weren’t being productive and putting your best foot forward, you were just wasting your time, and no one cared how old you were.

  I didn’t give my age a second thought. I was just sure I could make it work.

  We hired a casting director; I took the video camera that I always carried and put it on a tripod, and we brought actors in to read; we cast Kidada and her fiancé, Jeffrey Nash, who was interested in acting. Under my dad’s recommendation, Mary Pat and I flew out to Los Angeles together and shopped the movie around, trying to get Hollywood involved. Sidney Poitier was Kidada’s godfather, and I called him.

  That’s right. I cold-called Sidney Poitier.

  “Hello, may I please speak with Mr. Poitier? This is Ally Hilfiger calling. Kidada Jones gave me this number to call.”

  A mature female voice paused on the other end of the line. Finally she said, “Please hold on, I will get him.”

  My heart was racing, my palms were sweating, and I was barely able to breathe.

  “Hello, Mr. Poitier,” I said. “I am very sorry to disturb you, but Kidada told me I had to call you.”

  “Oh, of course, Kidada. She’s a great kid.”

  “Yes! Well, I am producing a film based on African-Americans being ranked in the navy during World War Two.”

  “Very impressive. Good for you!”

  “Thank you! We are very eager to get this off the ground and hopefully get these war veterans the commendation they have been waiting for for so many years. We just need a big name to star in the movie. Are you interested?”

  Holding my breath, waiting for the shoe to drop…

  “Sounds really interesting, but I don’t think I’m available,” the Hollywood legend said.

  After Mr. Poitier, the rest of my cold calls were cake.

  Jeffrey Nash’s sister is married to Forest Whitaker, and we went to the actor’s house to ask him to play our lead. He also politely declined. We ended up casting his beautiful wife in a small role. When Denzel Washington was in Mustique vacationing with his family, my dad invited him and his family to our house for lunch. I didn’t hesitate for a second to ask him. Denzel seemed shocked that a sixteen-year-old was pitching a film to him, but he was very nice and humored me. I gave him the script and told him about the movie, but he said he wasn’t doing movies for a while.

  I really grew a real pair swinging down there. What did I have to lose? The story had purpose. It wasn’t selfish or vacant, and because of that I wasn’t afraid. There is also something about a sixteen-year-old girl, a force like no other entity in this world, and I was accessing every bit of my teenage blind courage.

  We ended up with a great cast. Along with Kidada and Jeffery, it included Stephen Rea, Aidan Quinn, and Ossie Davis in his last movie role. It was perfect.

  Now all we had to do was shoot the damn film.

  For three months we filmed in Buffalo on a destroyer escort naval ship that looked like the USS Mason. Three months in the winter, in Buffalo! We also shot interior scenes in Elmira for three weeks. During the drive up there, we got caught in a major blizzard on the highway, so we followed eighteen-wheelers that blocked the snow. My aunt Betsy had a Tommy Hilfiger outlet store in Elmira and gave us big, puffy down jackets to wear.

  That was a special time for me, because I stayed with Nonnie. I would come home late at night and have the loveliest and coziest conversations with my grandmother about life. I would lie in my bed and on her way to her bedroom she would stop and say, “Honey, are you lonesome?” She’d come in and sit with me. She knew that things were difficult with my mom and that I wasn’t always feeling well. I didn’t have friends my age around me at all during the filming; I was among adults thirty years old and up. And I was to be considered their “superior” because I was the producer. It made things awkward, to say the least.

  My joints were sore around this time but I sucked it up and trudged ahead—with a lot of weed to help me after the day was over. I hung out with the makeup, hair, and costume people and made friends with some of the extras. Because the story was about young African-American sailors, we hired a lot of young African-American guys from Buffalo when we were shooting there. As I was the youngest (by far) on the production side, it was my job to be the liaison between the cast and crew. Though stressful sometimes, it was a lot of fun. I loved meeting new people and having new experiences.

  When we finished shooting in Buffalo, we went to Ireland to film a few scenes and my dad came along to help because we couldn’t afford to bring our wardrobe crew on the trip. To dress the extras my father and I scoured the local salvage and thrift shops and dug through old garbage bags filled with moldy clothes. We didn’t have enough extras, so my dad and I put on the smelly clothes and acted as extras in our own movie. (We used John Hume, too, the Nobel Peace Prize winner, who was a friend of Mary Pat’s!)

  In one scene, as an extra, my dad was handing out Guinness Stouts to the townspeople. I did the hair and makeup. We hired local women as extras. When they found out they were going to be in a movie they immediately went out and got their hair done. I had to redo all of their hairdos to fit the period. It was mayhem! I had bobby pins in my mouth, tape rolls around my wrists, safety pins stuck to my shirt, and combs in my back pockets. It was a role I’d play again in my twenties when I became a fashion stylist.

  Though I have Irish blood from Nonnie’s side of the family, it must not have been thick enough because I froze in Ireland, which made the aches in my joints almost unbearable.

  Somehow we pulled it off. Proud opened in about ten cities. The film is far from perfect, but it’s filled with the heart and soul of a project made with a higher purpose in mind. We got some very kind reviews and into at least one prestigious film festival.

  Proud still lives and breathes, too. It’s available on Netflix and is now part of an exhibit in the Smithsonian. Sometimes when I am flipping through the movie channels, I see it playing on Starz. It makes me feel—well, proud!

  The summer after the release of the movie, I lived on Nantucket, wilded out, and partied way too much, but had the time of my life. I wanted to be a normal kid, but maybe my version of “normal” was a little off the scale. I hung out with college kids and fell in love with Led Zeppelin albums and listened to them with reckless abandon. I wanted to live in the 1960s and ’70s, so I just pretended I did!

  On Nantucket, I got a job working at a bikini shack shop on the beach. From when I was eleven years old, I had had summer jobs on Nantucket. I worked as a babysitter for a couple of different families, including for a woman whose mother was an editor at Vogue. I also worked in a beauty shop and for my mom in her store, The Children’s Shop. At the bikini shack I was a great salesgirl. I was helpful and honest enough to gain the trust of the customers. I remember leading one mother of four kids gently away from the string bikinis and to the low-cut one-pieces. I also remember a very old and cranky gentleman with a young trophy wife who wanted four bikinis with different bottoms and shoes to match each outfit. The man told me he was in a rush and became very, very impatient with me. As I was carefully wrapping the merchandise in hot pink tissue paper, he began demanding that I give him the grand total of the transaction right away. Just my luck, that moment I had an attack of Lyme brain and my math skills went out the window. The man called me an idiot because I couldn’t add properly. I felt like a big enough idiot as it was!

  One of my coworkers rescued me and completed the transaction. I locked myself in one of the bathroom stalls and sobbed my eyes out. I knew I had made a fool of myself, and I knew that my brain was failing me more and more.

  On Nantucket I also created, produced, and starred in a show on Nantucket TV called In the House with Ally Hilfiger. I got the idea for the show when I was staying with Kidada in Los Angeles. She introduced me to Cary Woods, one of the producers of the movie Kids. I stayed at Cary’s house a couple of nights on his couch after eating too much Chinese food. He was awesome and we got along famously. He was the cochairman and creative officer of Plum TV, a cable provider that targeted wealthy communities.

  He wanted me to have my own TV show on the network. In the House with Ally Hilfiger took its inspiration from the MTV show Cribs. I went to people’s summer homes with a video camera, took a little tour, and asked questions like, “How do you decorate your house for the Fourth of July? What is your perfect outfit to wear to the beach while riding your bicycle? How does your home epitomize Nantucket? Why do you love it here? What is in your closet and in your garage?” I had a ball and I felt as if I was doing something productive for my future.

  It would be an article in New York magazine that summer, however, that would have the biggest effect on my future. They interviewed me about being a movie producer at the age of sixteen, and the story they ran would open the door to a reality TV show—and some of the darkest months of my life.

  nine

  IN ANGEL’S WINGS… AND HANDCUFFED

  “Many Lyme disease patients have acquired attention impairments which were not present before the onset of the disease. There may be difficulty sustaining attention, increased distractibility when frustrated, and a greater difficulty prioritizing which perceptions are deserving of a higher allocation of attention.”8