When I was nineteen I shared an apartment in Manhattan with the jazz singer Annie Ross, and it led to my doing something I now wish I hadn’t. She was fifty-eight at the time. It was 1989. We were on the sleepy northern end of York Avenue in a giant postwar building, one with a semicircular driveway in front and two columns of balconies on the facade. The apartment belonged to my girlfriend’s step-grandmother, who lived off and on in Los Angeles. Annie was an old friend of hers and would usually stay there when she visited New York. I was doing an open-ended apartment-sit, looking after the cat. One day my girlfriend said that Annie was coming to town and would be staying with me for a while. I had met her on one of her previous visits—she was friendly and husky-voiced, with a big laugh—so I was fine with the idea. Not that I really had a choice.

Annie had hit it big in the early 1950s as a glamorous and jaunty solo performer who sang with deftness and wit. In 1957 she became an international star as part of the virtuosic vocalese trio Lambert, Hendricks & Ross, vocalese meaning they sang lyrics they’d concocted to replicate instrumental jazz solos. By the ’80s Annie was mainly acting in small movie roles; that’s her getting turned into an evil robot in Superman III. Most of this was unknown to me then. When my girlfriend and I were still in high school together, she had played her parents’ Lambert, Hendricks & Ross albums for me, and I got a kick out of them, but I would’ve been a lot more excited if Lou Reed or one of the members of R.E.M. were moving in.

New York was already my home. I’d grown up and gone to high school less than ten blocks from the apartment on York Avenue. I was supposed to be in college upstate at Vassar that spring, but after my first semester I’d failed out. I wasn’t sure exactly why. In high school I was flummoxed by math and science and struggled to keep up in virtually any class that wasn’t English. If my girlfriend—let’s call her Daphne—hadn’t helped me prepare for my senior-year astronomy final, I might not have graduated. I hoped a small college where I could focus on literature, writing, and art would be the answer. But after giving it an earnest try for three months, I floundered. A sort of paralysis set in. I couldn’t write, I stopped reading. I agonized to the point of despair over my academic incapacity, but there were things I knew I was doing right: making friends, watching old movies in the student theater practically every evening, staying up late in conversation.

I accompanied one friend to an introductory meeting of the campus literary magazine. To become junior editors we were supposed to fill out a sheet describing ourselves, but we found the editor-in-chief so pompous that we made up a grandiose bio and submitted it under a fake name instead. My roommate, a billiards ace from Philadelphia, taught me how to shoot pool. I nursed a major crush on a wry sophomore from Minnesota who had a Lambert, Hendricks & Ross album in her cassette collection. A classmate from Oregon told me over a meal in the dining hall that she’d always thought she’d marry a Jewish man from New York, and I wondered, Why would anyone want to do that? I went to hear Mary McCarthy read from The Group on the twenty-fifth anniversary of its publication; she seemed formidable, and with her white bouffant and red pantsuit she resembled Barbara Bush. In the campus chapel I listened to the critic Alfred Kazin deliver a lecture on American literature and get testy when a student asked afterward why he hadn’t mentioned any female writers. A full-page New York Times ad in which Donald Trump crowed about his recent purchase of the Plaza Hotel prompted a revelatory discussion with a Long Islander who lived across the hall from me: He was the first person I’d met who didn’t consider Trump a buffoon, and I was the first person he’d met who didn’t consider Trump a role model.

In the English class I failed that semester, we read Where You’ll Find Me, a short-story collection by Ann Beattie. One story was about a nineteen-year-old named Oren who’s living with his father and stepmother and working at a bookstore after getting booted from college. “The fact that he had flunked out of school hung over everything like a cloud,” Beattie wrote. The story ended with his father kicking him out of the house, which distressed me so much that I almost wrote Beattie a letter asking for reassurance. Would Oren be okay? I needed to know. We didn’t even find out why he had flunked out. My own nemesis, I would discover only decades later, was attention deficit disorder. Spoken instructions flustered me, school workloads overwhelmed me, background noise drove me mad. I functioned best when focused on a single activity, ideally a solitary one.

Like Oren, I felt the humiliation of failing out compounded by being back home with my parents. I argued with my mother, who was working fourteen-hour days as a psychiatrist, about whether it was right or wrong for me to sleep during the day. My father worked healthier hours but was no less devoted to his field, cardiovascular pharmacology. They regarded my inertia with concern and perplexity. I yearned for a place to myself. By April, when I moved into Daphne’s step-grandmother’s apartment—two weeks after my nineteenth birthday, and two weeks before I spotted Mia Farrow in Central Park walking her toddler son Satchel, who now goes by Ronan, on a leash—I was working at a video store near Gramercy Park and interning at the Village Voice. As a cinephile and an aspiring journalist, I thought I’d hit the jackpot. At the Voice I was a research assistant to the paper’s new media critic, Doug Ireland, a pear-shaped, wickedly funny man who offered to pay me with pot. He smoked it in his office along with cigars. The video store claimed to have the city’s biggest selection of movies, and clerks could borrow them for free. Videotapes were shelved floor-to-ceiling behind the counter in alphabetical order, which meant The Sorrow and the Pity stood alongside Sorority House Massacre. Many of the clerks were students at the School of Visual Arts across the street. All day or night we’d listen to the Velvet Underground, Pixies, T. Rex, and a compilation of Elvis Presley’s most egregious covers. His version of “Old MacDonald” was a standout.

Daphne, a high-school junior, stayed over in the apartment with me once or twice a week. Mostly I was alone with the cat. His name was Trinky, after Trinculo, the Tempest character. Theirs was a show-biz family. The apartment, a two-bedroom, contained an Oscar that Daphne’s grandfather had won in the ’40s. For decades he’d been a Hollywood songwriter. The Oscar rested on a grand piano next to sheet music for his songs. Beside the piano, the living room had a towering art deco lamp, a coffee table supporting a marble Buddha, and a shaggy orange carpet. Framed photos of Daphne and her brother were everywhere. Her step-grandmother, the songwriter’s third wife, had been a cabaret singer. Maybe that was how she’d befriended Annie Ross; I wasn’t sure. For me Annie’s imminent arrival was just another thing to stay on top of, along with my jobs and groceries and Trinky’s litter box and the driver’s-ed classes I was taking.

It was my first time living alone. I savored it. Solitude was my preferred state. At sixteen I’d started going to movies by myself, and I was always reading. I read The Stranger while walking home from my summer job as a Häagen-Dazs counter person. Books, movies, and music were immersive experiences, things I could comfortably get lost in. Central Park too was a kind of rustic isolation chamber, perfect for a teenager unaware of his ADD. One spring day in tenth grade, when there was a history paper due that I hadn’t written, I cut school and spent hours on a bench in Central Park with my library books and a notepad, writing the paper longhand. I enjoyed it: the sunshine, the quiet, being able to concentrate on one task all day.

Bookishness was part of what united me and Daphne my senior year. We met through our school’s literary magazine. She was sharp-edged and wise. A few weeks after that first semester of college, when we’d been together a year, I tried to break up with her; I wanted to return to Vassar untethered. She refused. I conceded. And then I got suspended, so a breakup seemed pointless. My moving in to her step-grandmother’s apartment worked for us: we could see each other often but not too often, and I could otherwise be alone with my books, my writing, and my stack of movies from the video store. Then Annie moved in.

I’d been told that Annie was an ex of Lenny Bruce’s. I wasn’t told that when they were involved, at the height of her fame in the late ’50s, she’d been a heroin addict. Lenny and a friend saved her life one night when she overdosed. I didn’t know she was born outside London to Scottish vaudevillian parents and moved to the US when she was four; or that she’d appeared in the Our Gang series, singing in a kilt, when she was seven; or that she’d played Judy Garland’s kid sister in the movie Presenting Lily Mars at twelve; or that at twenty she’d had a son with the drummer Kenny Clarke and gave the boy to Clarke’s brother and his wife to raise; or that at twenty-two she’d written the lyrics to her signature song, “Twisted,” a number so clever and fleet that if you haven’t heard it, you haven’t lived. I also didn’t know that in the early ’50s she’d subbed for one of her idols, Billie Holiday, at the Apollo Theater in Harlem and impressed Billie so much that they became close; or that she’d performed with Duke Ellington and Lester Young and Art Blakey and so many other musicians I would come to adore; or that, while living in London in the ’60s, she married an actor, Sean Lynch, and opened a jazz club with him that thrived for about a year; or that by 1975 she was divorced, bankrupt, and homeless; or that, when she came to stay with me, she wasn’t singing much anymore. This was the age before Google. What I knew was that she was visiting New York to attend the memorial of Max Gordon, a jazz impresario who had run the Village Vanguard nightclub for five decades, and that she liked to drink.

Annie had the presence and diction of a lifelong actress. I want to say she made a dramatic entrance into the apartment, flinging aside her carry-on and breaking into song, but she was too poised for that. And I was out at one of my jobs when she arrived. I’d been sleeping in the little guest room since moving in the previous month, so Annie took the big bedroom, where the TV and VCR were. She remembered having met me the previous year. She was kind and lighthearted, and she was fond of Daphne and her family. Her hair was dyed red and teased out. Her clothes didn’t make an impression on me—my own idea of style back then was a thrift-store suit jacket over a Strand Bookstore T-shirt—but she came across as a bohemian bon vivant.

If I’d asked, or been willing to listen, I might have learned that before me she’d had many roommates. Over the years she shared flats and hot plates with the singers Blossom Dearie and Georgia Brown, the pianist John Lewis, a six-foot-two stripper named Rusty Lane, and Charlie Parker. We didn’t cook together in our apartment’s narrow galley kitchen, but if we had she might have told me she’d once written a cookbook. The title was Annie Ross Says ‘Come On In!’ and Try Her Favourite Recipes. On the cover she’s sitting on a kitchen counter in a black evening dress holding a very full goblet of wine, her auburn hair exploding into a massive shag.

The book was published in London in 1972, the same year she played Jenny to Vanessa Redgrave’s Polly in a West End production of The Threepenny Opera. With rock ’n’ roll supplanting jazz in popular taste, Annie had to find new outlets for her singing. Meanwhile, in the States, her voice was being rediscovered. Both Bette Midler and Joni Mitchell covered “Twisted” on the albums they recorded in 1973, each in their own style: Midler’s a burlesque, Mitchell’s a lark with a Cheech & Chong cameo. The Village Voice jazz critic Gary Giddins would eventually write about “that strange period in the ’70s” when “all white woman singers tried to sound like Annie Ross.” By the ’70s mainstream culture had caught up with the psychoanalysis-mocking humor of her “Twisted” lyrics (“My analyst told me that I was right out of my head / He said I’d need treatment but I’m not that easily led”), which upon its release in 1952 put the song squarely in the realm of jazz hipsterism.

“Twisted” was born when she met a record producer in New York who asked if she’d heard “Moody’s Mood for Love”—the first popular vocalese song, though the term hadn’t been coined yet—and if she could write the words to something like it. She said yes. The melody and title of “Twisted,” a 1949 composition by the saxophonist Wardell Gray, grabbed her, so she went home and wrote the words that night. “But I wasn’t in analysis, like in the song,” she told an interviewer in 2005. What inspired the lyrics? “Money,” she quipped. “I was working as a waitress, hated it, and wasn’t any good at it.” She offered a more considered answer in the 2012 BBC documentary No One but Me: “I was writing about my aunt.” Her aunt, the Hollywood and Broadway singer Ella Logan, raised her in Los Angeles after her parents returned to Scotland to resume their vaudeville careers. (Annie’s older brother Jimmy remained in Scotland and, as Jimmy Logan, became the country’s most beloved entertainer this side of Sean Connery.) “One day I was growing up,” Annie recalled in the documentary, “and my aunt said to me, ‘Why don’t you become a set designer, because you can’t sing—you haven’t got the magic.’” The song is a riposte, not to an analyst but to a competitive and discouraging caretaker. “One night, I actually sang ‘My aunt always told me,’” Annie said. Her lyrics were far wittier, and in this case far more personal, than those of “Moody’s Mood” and the other vocalese numbers that prevailed until she joined up with Jon Hendricks and Dave Lambert and conquered the genre.

This is the person I was living with. A trouper. Someone for whom sharing space with a teenage acquaintance was merely a gentle curve in an eventful life. I liked her, and she was hardly an authority figure, but part of me just didn’t want her there.

One night she came home laughing with a man in a suit. She introduced him to me as Sidney. While she excused herself, he engaged me amiably, and he lit up when I mentioned my internship. “Tell Dougie his old pal Sid Zion says hello,” he said. I recognized his name: the newspaper reporter and columnist whose flattering biography of his buddy Roy Cohn had come out the year before. We’d discussed it in American Culture class my last semester of high school, wondering how anyone could defend, let alone befriend, Joe McCarthy’s pit bull. And he was chummy with a leftist gadfly like Doug Ireland? The world of adults bewildered me. In any case, Sid seemed like a lot of fun. Maybe he and Annie were returning from Max Gordon’s memorial that night. I remember imagining their evening must have involved the restaurant Elaine’s, a couple of blocks from the apartment. I had never been there, but like any Spy magazine devotee, I knew it as the favored carousing spot of authors and actors. When Annie reemerged, they set out again.

Another night I was working at a small table in the living room where I’d set up my computer—I was constantly writing letters to friends in college or reviews for myself of the movies I was watching—when Annie came home tipsy with a boisterous group. Seeing me tapping at my Mac, she apologized and led the group into her bedroom. I was mortified: the schoolboy uninvited to the grownups’ party.

One of the movies I wrote about at that table was Let’s Get Lost, Bruce Weber’s documentary about the trumpeter Chet Baker. I’d gone to see it downtown at Film Forum a few days before Annie moved in. Like Annie, Baker became famous in the ’50s and grappled with a heroin addiction. Unlike Annie, he never kicked it. If I’d thought to ask whether she’d seen the movie, I might have learned they recorded an album together, or rather half of one. On Annie Sings a Song with Mulligan!, released in 1958, Annie was backed by the Gerry Mulligan Quartet with Baker on trumpet. It’s her best recording. Her rendition of “I Feel Pretty,” from West Side Story, is elating. But, as she’s explained in interviews, “We cut one side and Chet Baker went to the toilet and never came back.” His mind was elsewhere. Annie’s habit may have started by then too. I was stunned by Let’s Get Lost, yet I was oblivious to the jazz survivor in my midst.

Annie’s habit had definitely begun by 1959. She and Lenny Bruce were involved for the first half of that year. His biographers Albert Goldman and Lawrence Schiller wrote that Annie was off drugs when they met and that Lenny “turned her right back on again.” Still, they were happy. They got engaged. “Lenny used to send me love letters on airsick bags,” she would recall. “He was sweet and thoughtful and loving and funny.” Like the Beats’ poems, his onstage patter was influenced as much by jazz as by drugs. He and Annie were together when he got his biggest break, an appearance on The Steve Allen Show. The act he did that April evening was faithfully re-created in 2018 for the Season 2 finale of the Amazon series The Marvelous Mrs. Maisel, with the Midge Maisel character watching from backstage. Accompanied by Allen on piano, Lenny performed a song-monologue about breaking up with your wife and convincing yourself that you’re happier single. As a routine it’s a bit maudlin and occasionally spiteful; for Mrs. Maisel’s writers it’s a vehicle for Midge’s epiphany about comedians’ inevitable loneliness. “When she’s old, then she’s gonna be sorry,” Lenny says. “She’s young and swinging now and she can get a lot of guys, but when she’s old—I can see her about twenty years from now: ‘How you doing, Annie?’”

That summer, with each of them touring and Lenny reconnecting with his ex-wife, who’d just finished serving a two-year prison sentence, the relationship fell apart. Billie Holiday died in New York that same summer, at forty-four. Annie had tried to visit her in the hospital some days earlier, stopping by between shows across town at the Apollo, but visitors were no longer allowed because one friend had slipped Billie a packet of heroin. Annie would later say that whoever gave Billie the heroin was being merciful, since while slowly dying of cirrhosis she was also going cold turkey.

In 1962 Annie moved to London in a last-ditch attempt to get clean. That year Lambert, Hendricks & Ross won a Grammy, for best performance by a vocal group, but she didn’t know it. “I’d love to see that Grammy, because I was in Europe, apparently,” she said in 2011. Among the friends she made or re-encountered in London was James Baldwin, whom she’d first befriended while living in Paris in 1949 and ’50, when she was a nineteen-year-old club singer sharing a hotel room with Kenny Clarke. “We were poor, really poor,” she would say. “Jimmy, who I knew as a writer who was working on books and stuff, he and I used to collect milk bottles, cash them in, buy some food.” When they were reintroduced in London in the ’60s, by the critic Kenneth Tynan, it was at a fancy restaurant.

If I’d shown some interest, maybe Annie would have told me some of these stories. As it was, we were simply polite with each other. Daphne’s step-grandmother had surely asked her to be on her best behavior around me. And she was considerate to begin with. She probably had no idea I felt encroached upon. I probably didn’t realize it myself.

By this time I’d been at the Voice about six weeks, and I loved it. Paralysis didn’t afflict me there. I told a friend in a letter, “When Doug says, ‘Lawrence, an article was pulled at the last minute from today’s Daily News. Get me the article; talk to the editors and find out why they pulled it; talk to the author and get his side of the story. I want the information and the article by five p.m.,’ I do it.” And while downtown wasn’t new to me, the Voice office of wisecrackers and muckrakers was, and it felt worlds away from the Upper East Side.

Donald Suggs, the research chief, warned me with a grin that the words “cherry vanilla” on the back of my Häagen-Dazs T-shirt would be misinterpreted if I wore it in the meatpacking district. Frank Ruscitti, the guy who manned the editorial phone line, would answer it with whatever was on his mind. “Why do you think they call it jewelry?” he said to one caller the day the Voice reported that Professor Griff of Public Enemy had made some stupid anti-Semitic remarks. Nat Hentoff had been writing his Voice column for thirty years by then, but his office looked like he’d occupied it for centuries—stacks of books and papers towering on every surface, his bearded and soft-spoken self hidden behind them. I was unaware how significant his writing about jazz had been in the ’50s, and also unaware that Gary Giddins was then halfway into his three-decade run as the staff jazz critic. The editor Mim Udovitch, whose office was next to Doug’s and who dressed like Madonna in Desperately Seeking Susan, exuded a sassy aplomb that came through in her writing. And Doug, emerging from the haze of his office, always wanted to know what book I was reading. I’d found my people. I could already envision a future for myself beyond school. It was thrilling.

Uptown, Annie stayed on for a couple of weeks. It would have been longer, except for what I did.

I kicked her out.

Actually, that’s not quite true. I told Daphne that Annie’s friends were a distraction, impinging on my quiet and solitude. She told her step-grandmother. And then one evening Annie asked if we could talk.

We sat together on the living room couch, orange carpet underfoot. She looked concerned. She was very sorry to learn that she and her friends were troubling me. I thanked her and tried to assure her that wasn’t the case. Solemnly, she asked, “Would it be better if I left?”

Her face was resigned, as if she were used to things not working out. She was slurring slightly. Maybe she looked a little hurt. But her bearing was gentle and not at all irritated.

“Yes, I think it would,” I said.

She gave me an opening and I took it. I could have laughed it off and said it was all a misunderstanding, but I didn’t. By playing along I could go back to living alone.

Annie moved out the next day, when I was at work. I assume it was out of politeness and respect for our absent host that she didn’t put up any resistance.

Did I realize that getting her to leave was selfish? I saw no connection between kicking her out and my own fear of being kicked out—of there, of college, of my parents’ home. I felt like I didn’t deserve anything, even while I felt entitled to someone else’s apartment. I didn’t see that I was lashing out, at Daphne for not letting me break up with her, at Daphne’s step-grandmother for her inexplicable generosity and that hideous carpet, at my parents for their unconditional and therefore unearned affection and support. Legally I’d been an adult for a year, but I was still a teenager. However evolved one might be at nineteen, in vital ways one is still a pupa. Feelings are amplified to excruciation—as perhaps Annie felt at nineteen when she discovered she was pregnant. Maybe solitude felt crucial to me because I was so susceptible to distraction. Maybe my shyness made having occasional strangers in the apartment intolerable. It’s possible, though, that I really just wanted access to the TV again.

Soon after, on the eve of her last day of eleventh grade, Daphne broke up with me. We’d been wearing on each other, and I’d refused to attend her prom. Instead I’d spent the night in her step-grandmother’s bed with the wry Minnesotan I’d had a crush on at Vassar, who was in town to catch a flight from JFK in the morning.

In July Daphne’s step-grandmother returned from LA and I moved back in with my parents. At the Voice I started working on the letters section, two pages of fervid correspondence punctuated with comics by Jules Feiffer, Lynda Barry, and Matt Groening. I gave each letter a headline like “Do the White Thing” or “Dread Poets Society.” The editor I assisted, Ron Plotkin, typed so hard that most of the keys on his keyboard were blank. At the video store I rolled my eyes at customers asking to rent Caddyshack II. I passed my driver’s test on my second try. In August I went back to Vassar and completed my freshman year, also on my second try.

After bumbling through a sophomore semester I left college again, this time by choice, and moved to San Francisco. I needed to get further than a train ride away from home to figure myself out. There I worked in an enormous bookstore—among dancers, dropouts, musicians, graduate students, and aging bohemians—and at another alternative weekly paper, reviewing movies and reporting news stories. I got to interview the Pixies’ lead singer and songwriter, Black Francis. The first thing he said was: “You’re not going to ask me what we sound like, are you?” After hours the paper’s senior editor, Andrew O’Hehir, mixed me my first martini and schooled me in jazz. I returned to Vassar after a year, when I grasped how much more I had to learn, and because of the haunted look on the face of one of my bookstore colleagues when he told me he’d almost completed college back east some years earlier and was still hoping to finish his senior thesis.

In 1993 I was writing my own senior thesis, about depictions of journalists in movies, when Robert Altman released Short Cuts, his three-hour film intertwining the plot lines of several short stories by Raymond Carver. I went to see it by myself on the Upper East Side. Altman was one of my cinematic heroes, up there with Hitchcock, Polanski, Kubrick, and Scorsese. There onscreen was Annie Ross, playing a boozy, beleaguered nightclub singer, a role Altman invented for her. Her desolate songs served as the movie’s backbone. They echoed the tragedies of her character’s past and possibly her own. The character lacked Annie’s wit, but she had her discernment and, of course, her voice. Annie acted among a huge, talented cast that included Lily Tomlin, Tom Waits, Julianne Moore, Jennifer Jason Leigh, and Frances McDormand. I was happy for her, and I felt like an idiot. The young man so enamored of creativity had thrown out a woman who embodied it.

The attention that Short Cuts brought Annie inspired her to resume singing on stage, at sixty-three. She performed around the world, reuniting with Jon Hendricks for a tour in 1999. (Their bandmate Dave Lambert died in a car accident in 1966.) Her voice had roughened, but she got by on charm. She had a weekly cabaret gig in Manhattan from 2007 to 2017, when she was eighty-seven.

The Village Voice is gone, and so are video stores, but Annie’s still around. Admirers post selfies with her on Instagram. She’s been canonized: in 2010 the National Endowment for the Arts proclaimed her a Jazz Master, and in 2013 the Library of America anthology The Cool School: Writing from America’s Hip Underground included her “Twisted” lyrics among work by countercultural icons like Kerouac, Burroughs, Mailer, Warhol, Dylan, and her onetime fiancé Lenny Bruce. In interviews it’s clear her memory is durable, along with her humor and her relish for spinning anecdotes about the artists she’s known. She often contends that jazz is as much about paying attention as it is about performing. When I think of something she said along those lines in a 2015 conversation with a singing teacher, I can’t help taking it personally.

“From your vast experiences through the years,” the teacher asked, “is there anything you would offer young singers today as solo artists or performing in college jazz ensembles and groups?”

Annie replied, “It’s called listening.”