By Anya Schiffrin

Growing up on the Upper West Side in the 1970s, we kids were feral. We began taking the subway at the age of eight. By our teens we had graduated to screwdrivers — vodka with fresh orange juice, for $1.25 at Wilby’s on West 90th Street and Broadway. We roamed the streets. Sometimes we got mugged for our bus passes. Parents often went away for the weekends to Amagansett or Connecticut, and so we gathered, wherever there was an empty apartment, and got into mischief. The teenage boys lived most on the edge: writing graffiti, selling drugs, sometimes stealing from the places where they worked.

Most of us grew up, went to college, and led happy and productive lives. But some did not. They fell too far into drugs, got kicked out of school, had nervous breakdowns, occasionally died. I’ve often wondered what sort of book would capture our particular UWS teenage years. It was a shock when the handsome, privileged Rob Sedgwick got caught up in a notorious drug bust. Sedgwick’s memoir of that time, “Bob Goes to Jail,” is a beautifully written, frank, and funny description of a moment in Upper West Side history and a powerful recounting of the mistakes of youth. 

When we were teenagers, the Sedgwicks were the influencers in our group. They were talented, kind, generous, and related to Andy Warhol muse Edie Sedgwick, which impressed all of us. The youngest was Kyra who later became a famous actor. Son Nikko, the middle child, is a painter, and older brother Rob also became an actor, appearing in the soap opera Another World and movies such as “Die Hard With A Vengeance,” “Banshee,” and “Tales from the Dark Side.”

Rob looked just like his father Henry Dwight Sedgwick V, a venture capitalist. We all knew him as Duke, but he receded a bit when Rob’s mother, Patsy, left him for the legendary art dealer Ben Heller who is known for his early “embrace” of the Abstract Expressionism movement. Ben was highly influential in the New York art world, and his superb collection at one time included works by Pollock, de Kooning, Rothko, Rauschenberg, and others. “Ben was brilliant. He was a colossal force,” Rob Sedgwick remembers. The details are lost in the mists of time, but the kids still tell the story about the time Heller bought a Pollock only to find it didn’t fit in the car or on the wall of his apartment. Somehow, they managed to get it home and ended up stapling it to the ceiling. 

When I met the Sedgwick/Heller family, they had moved from the West Side to a large East Side townhouse on East 73rd Street. The kids lived in their own world — a bubble of music and jokes and a close circle of old friends. We’d look at Heller’s art collection, spend hours listening to Jimi Hendrix, Janis Joplin, and The Doors. At night we’d go to Central Park and sit on the mushroom next to the Alice in Wonderland statue. And by day, we spent hours gazing at the Van Gogh paintings in the Met (as we called the Metropolitan Museum of Art).

After graduating from Bennington College in Vermont, Sedgwick moved back to the UWS to begin his career as an actor. He spent some time in Los Angeles at one point, but was not a fan. “New York is a pain in the ass,” he told me, “but it’s home.”

For a time, he moved into his grandparents’ place on West 85th Street off Broadway; his grandparents wintered in Tobago. “Bob Goes to Jail” is his recounting of a fallow period in his acting career when he drank too much, dated a stripper, and foolishly agreed to let “Jordan,” a drug dealer friend of his brother, store 500 pounds of pot at his grandparents’ place on 85th Street. The results were predictably disastrous. Rob is unsparing as he describes his arrest, the police, the lawyers, the judge, the shady cast of characters, and his decision to provide information about the others involved in the crime. Cooperating led to Rob being let off with a four-year suspended sentence and 400 hours of community service. 

“Bob Goes to Jail,” published in 2021 by Rare Bird Books, begins with a dramatic account of Rob’s arrest and alternates between telling the story of what happened next with chapters about his childhood and his family. In the book most names are changed and Rob used the name Bob in the title as he thinks of Bob as his idiotic, irresponsible younger self. Except for a bit of time in LA, and some teenage years when Ben Heller moved the family to the East Side, Rob has lived his entire life on the Upper West Side so most of the book is set in our neighborhood. For many of us who grew up here, Bob Goes to Jail is a powerfully evocative description of our youth. The gritty backdrop of New York in the 1970s leads to sentences like: “The first time I got mugged was when I was around eight and we were living at 300 Central Park West….”

In the 1980s, Rob visited many of the old spots: Teachers, Red Baron on West 72nd Street, the Library, Teachers Too, Hanratty’s, the Irish bars, a night café on 106th and  Amsterdam. In his memoir, as Rob is arrested, he looks out the windows and spots familiar landmarks. “They shoved me into the cruiser. I looked out the windows at the Town Shop for brassieres, Shakespeare & Co., Zabar’s people freely walking up and down the wide boulevards of Broadway doing stuff. My inalienable right to wander around footloose and fancy-free just got snuffed. I was in the back of a cop car with my hands cuffed behind me, headed downtown.” 

In an interview, I asked Rob if he thought the neighborhood had changed a lot. In some ways, he said, the city doesn’t seem to have changed at all.

“Since the pandemic, the shit you see that’s happening in the subway — I kind of like it, because it is how it used to be. You used to have to watch your ass,” he said.

“[NYC] was a dangerous place to live. You had to have intestinal fortitude. You would run into [jazz drummer] Max Roach and [playwright] Leonard Melfi. There were great artists around. Artists can’t afford to live here now. It was a magic place. In the 1980s, Dad would take us to a restaurant that wasn’t a restaurant that served Haitian food. It was on the ground floor of a brownstone. I can still the taste the food.” 

Today, Rob, 63, is on West 111th Street and living a more settled life. He teaches acting and loves working with younger actors. He is shopping around his new play, Please Leave, set on the Upper West Side, which centers around an aspiring filmmaker and a group of homeless people who have been given temporary residence in the Hotel Gateau. Inspired by the UWS’s Lucerne Hotel, used during the pandemic to house people from city shelters, the play is a mix of satire, comedy, and tragedy and showcases Rob’s love of language and dialogue.

In the play, a major video streaming service makes a film that exploits the homeless situation at the Hotel Gateau for profit, awards, and attention. As Rob puts it in the play, it’s “Art we make out of others’ misery.” 

“There’s homelessness everywhere you look,” said Rob. “I don’t offer answers but wanted to bring it up.”

And that stripper Rob dated? In 2014, Rob learned that he had fathered a daughter. She’s 32 and got in touch with him for the first time to let him know she was moving to New York. She’s here now working in real estate. “She wrote a letter I will always keep,“ Rob recalled. “She is a blessing.”

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