When I moved in with Stewart Lupton, because all five members of our band, Jonathan Fire-Eater, moved in together, he fast dubbed me “Sarge.” I was the irritable bookkeeper and cleanliness monitor, inspired by the orderliness I’d seen in a photo spread on life in a modern submarine. Reality took the form of a rock band, which tends to go through more beer bottles and ashtrays. But our own spatial constraints weren’t entirely unlike those of a naval crew: five boys sharing a tiny fifth-floor one-bedroom on the Lower East Side. We later upgraded to a two bedroom, each bedroom with bunk beds, for the more challenging sum of $950 a month ($190 from each of us), and took on our guitarist Paul Maroon’s parakeet, Kim, named after Kim Gordon and Kim Deal. But disorder remained. After leaving town for Christmas, seriously under the weather, and returning to New York, I found a gift from Stewart, a book inscribed “to the Christmas grouch, my Tiny Tom.”

Stewart died last week at the age of 43, and, each day since, I’ve woken up feeling fine for a minute before sinking into a haze. Stewart never became the superstar he hoped—and, I’ll frankly say, deserved—to be, but one line that keeps coming back to me as I read the death notices and obituaries from afar is from Pete Townshend, talking about the premature deaths among his fellow musicians. “They may be your fucking icons,” he said, “but they’re my fucking friends!” I’m no Pete Townshend, but the sentiment resonates. This past week, articles have been describing Stewart as an emblem of many things—brilliance and thwarted promise, dissipation and hype, the 1990s and New York. But for me, he was a friend. When you live and work with such intensity with a small group of people at such a young age, as we did for the five years of the band, they enter your marrow.

Stewart wrote all our song lyrics, and he was one of the only poets I’ve known. I didn’t properly appreciate that dimension of his gifts until I was much older. His clever lines would stick with you. They could be about vicissitudes of fame (“I’ve been around so long, seen my face come and go”) or disillusionment (“Are you married to an unfaithful world?”). All were rich with atmosphere. You could be flying in a scene of dissolution, where “the lights are low in the aisle of the private jet, redhead getting sick on the carpet of the cockpit.” Or you could be somewhere in the past, as the “carriage lamps flicker past the docks and the crooked masts.” I liked them even when I didn’t get them, because they rocked: “I was struck by a painful notion, on a weekend trip to the ocean, that the high, gray seas will not recognize me through all this commotion.”

In one of our songs, Stewart sang, “Are you locked into a projection booth that shows the films of your troubled youth?” I am. Probably everyone, after the death of someone dear, is locked into a projection booth, with films of the departed playing in no particular order. One film: the bartender at Max Fish on Orchard Street is laughing delightedly as I order a round of Shirley Temples for myself and Stewart and the others in the summer of 1995. It’s on the house. All of us are back in New York after a break, and Stewart, barely 20, is free, we think, of the worst grips of his drug addiction. Another film: Stewart is playing me one of his favorite songs, “Spanish Harlem Incident,” from Another Side of Bob Dylan. I’m sitting on a $20 couch. The apartment tiny and dirty and covered with old yellowing linoleum, with a shower in the kitchen, and a slight breeze is coming from the window. We’re 19 and 20, all excitement and mission. Some of the films make me thoughtful, some make me smile, and some make me weep.

Stewart had genius, but what first made the world notice him was his daring. The sorrow tied to that quality has been mentioned in obituaries, for he gave most things a try, and narcotics were among them, devouring so many hopes. (How he hated falling prey to a cliché.) But the joy of it was that he said, sang, explored, and wrote what others wouldn’t. His jokes could be un-P.C. or obscene enough to make you gasp before the tears of laughter would erupt, and he would regularly pull off stunts like, say, running stark naked through the hallways of the Hotel Nikko (now the SLS) in Beverly Hills, with one hand covering his groin and an expression of faux panic. His stage routine could vary from terseness to charm to loquacity that, sometimes, would have the rest of us staring at the floor. His inspirations regularly teetered between brilliant and hokey, which may be the best sort. One small example: he suggested that the final song on our next record (never completed) should conclude with audio of us wrapping up a meal at a quietly busy restaurant. Was that sublime or lame? Stewart never overthought such things.

Some of Stewart’s finest boldness happened during songwriting, when the five of us were in a rehearsal space trying to thrash out an idea. A galumphing stretch in one song inspired Stewart to make gorilla sounds—Ooh-ah-ah! Ooh-ah-ah!—that left all of us convulsed. They became part of the song. (The singer has “read in the paper about a big, bad gorilla” who “escaped from the city zoo.”) During the writing of another song, for which Stewart had selected a poem he’d written about hoping to have daughters, Stewart joked about how he should count the band back in, suggesting, “Now give me daughters, and make them one, two, three . . . !” Again, all of us found it hilarious. But that became part of the song, too. The pains he took with his words never caused him to lapse into rigidity or self-importance.

The band broke up in the summer of 1998, plagued by tensions that weren’t manageable when Stewart’s addiction was thrown into the mix. Just over a month later, I was back in college, disoriented, and I threw myself into Columbia University’s core curriculum and tried not to think too much about what was lost. Three of my bandmates went on to found the Walkmen. Stewart, for his part, would later mark that moment as when “my house of cards came down and the world gave me an ass-whooping that became one in a series, the anthology of kicking the shit out of Stewart Lupton.” He kept making music and he kept writing words, many of them still beautiful. I’ll always love his line about the “shadow that’s caught in the hollow of your cheekbone” and the song that goes with it. But his troubles never abated for long, and, as happens with age, doors kept closing. I was in touch with him for short stretches, out of touch for long stretches.

In Stewart’s final years, he wasn’t always easy to reach, because he almost never answered his phone, and he had begun to hear voices, cruel and spiteful ones, in his head, preying on his worst fears. It must have been torture. When we did speak, though, the old Stewart—sweet, mordant, funny, wistful—would still come through. On one of the last visits I had with him, in the Mar Vista neighborhood of Los Angeles, he told me that he’d learned how to talk soothingly to housemates who were in mental crisis. “Then I notice,” he added, “everyone’s talking that way to me.”

Until I received the news that Stewart was gone, I never realized how hard I’d clung to a dream that he’d one day emerge into a quiet middle age, his demons laid mostly to rest, his genius properly revealed. I’ve had to focus on these hopes in order to let go of them, as if I were prying them out of my own grip, and lay them to rest, along with my friend. It’s a consolation, if a small one, that in his rough, final years I got to reconnect with Stewart and tell him that I thought he was brilliant and that I loved him. I still think so, and I still do.