Sign up for the Slatest to get the most insightful analysis, criticism, and advice out there, delivered to your inbox daily.

Two winters ago, more than a year after my old college roommate and dear friend Paul was diagnosed with ALS, he started making pictures. By then, he was gradually losing the ability to do almost everything else. He could still walk at that point, often through the leafy corner of his Boston neighborhood, Jamaica Plain, where the old tree limbs cradled the houses and the streets were barely wide enough for a car, but only with the help of a cane. A condition of the disease called bulbar palsy slowed his tongue to the point his words wobbled enough that he sounded as if he were drunk. He could eat solid foods, albeit with some trouble, and could drink the Relyvrio medication powder he swirled with a spoon into a glass of water twice daily—a prescription for ALS that last year clinical trials suggested was ineffective, and a cocktail so bitter it made him physically wince—but he began coughing more and more as he labored to swallow anything at all.

“I’ve got ALS, and there’s not a damn thing anyone can do about it,” he said in a group text with me and his other former college roommate, Evan.

Such moments of honesty would snap Evan and me back to the reality of his condition. We had named our group text after the street address of our old, yellow duplex in Columbia, Missouri. Through messages, Paul had remained largely upbeat in the face of a terminal prognosis, showing us that he was still a 42-year-old in the mood to live, and laugh. He sent us texts encouraging me and Evan, Paul’s best friend since childhood, to spare him no humor during the time we had left. So jokes and GIFs and memes became the rule. When he did share anything about his deterioration, those texts amounted to a kind of desperation. How much time did we have left?

Then he began showing us the “art” he was making.

Paul started “dabbling” in this art in late 2023, while confined mainly to his chair—both to pass the time and as a fun distraction from reality. He’d send us some of his creations over the group chat because he thought they were funny, but also because he thought we’d want to try it too. But I can’t say he, or we, actually created the images. He used his fingers, technically, but not in the way an artist holds a brush; Paul merely typed the words of what we wanted to see into the prompt bar of Midjourney, an A.I. image generator that posits to the user, simply and kind of horrifically, “What will you imagine?”

What would you imagine, that is, if you were dying in slow motion in front of two small children barely old enough to understand but aware that something is wrong, and a wife you fell in love with in high school?

This is what first slunk out of Paul’s imagination: “A man dressed as a bat sitting in a hot tub full of mashed potatoes.” No more than 10 or 15 seconds after he typed the prompt, Midjourney excreted four images based on those words onto his computer screen, like how photographers used to dissolve portraits into existence by hanging pictures from strings in a dark room. To us, they looked like real paintings, as if a classical artist a few hundred years ago had been compelled to complete four different variations of a man with pointy ears wearing a bat suit, ensconced to midchest in a vat of white, bubbly goo.

In one picture, this man throws a handful of the substance into the air. In another, by some sort of robotic misunderstanding of the prompt, the “mashed potatoes” look like giant testicles, and his human face is replaced by something like a Batman mask. That no painter would ever do this made it all the more humorous, and almost inconceivable, to each of us.

Evan and I didn’t have much idea how it worked. “It’s based on the words,” Paul, a biomedical engineer at MIT and one of the most intelligent people I know, explained. “From its training data, certain words will become associated with certain image patterns. When you put in a prompt, it will ‘predict’ what should be there.”

Raised in rural Missouri and a fan of the Kansas City Chiefs, Paul “asked” Midjourney to depict the team playing a game in hell. Soon, images appeared of the grass surface at Arrowhead Stadium replaced by luminous magma under a sky writhing with a giant blood clot, thousands of skeletons dancing or contorting in pain on the field and in the stands. Other Paul prompts included: “This couch eats people,” “A world without pants,” and “Santa Claus in the style of Yayoi Kusama.”

When Paul could no longer get around with the cane, then a walker, and was forced to consider immobility, he started making images like “Blue hedgehog pushing wheelchair amazingly fast” and “Photo of old man pushing friend in racing wheelchair.” Evan and I had no real idea how to talk with him about this. It was inconceivable to us that Paul, a man who used to be a tall, lithe defensive end in high school, would eventually need help simply moving around. We were losing a friend, fingers and toes at a time.

A couple of months later, Paul took part in a Boston 10K race in a Hoyt chair, a specially designed wheelchair that allows people with disabilities to participate in races, co-piloted by his friend Steve. On our text thread, it was pretty easy to avoid ALS by merely not speaking about it (unless Paul brought it up). But in person, as he and Steve rounded the street corner to where we could see them turn for the finish, the disease was right in front of us. I was in downtown Boston with Paul’s wife, Melanie, his two boys, and some of their other friends, with handmade signs cheering him on, while watching him try to pump his shriveling arms in the rain. When I returned home, I muddled around in silence for a few days. My wife didn’t need to ask what anguish was occupying my mind.

Pretty quickly, Evan and I started “making” A.I. pictures with our own prompts too. Some of mine included “Uncle Alvin sitting on the porch with the old god Leviathan,” “Giant bears attack a school bus,” and “Mourners gather at a funeral in front of an open coffin of refried beans.” Evan made pieces such as “The Gravy Man goes to prom” and “It’s my birthday, motherfucker!” Any mind blurt or ridiculous thought that minnowed behind our eyeballs Midjourney absorbed and spat out.

We—it?—made thousands of images. Midjourney created almost everything (though prudish in its limitations of no curse words or sexual innuendo), prompted in any artistic style. While we made images to cheer him up, Evan and I have spent as much time as we can with Paul the past couple of years, watching his mind and his sense of humor remain sharp while every other part of him fades away. We walked with him next to the ocean in Folly Beach, South Carolina, as Paul dredged his bare feet into the water and sand and felt the little pebbles and seashells for what turned out to be the very last time. We flew with him to St. Louis and pushed Paul through the airport in his wheelchair, to a rented van big enough to store it. We drove to Columbia, Missouri, without stating any real intention for the trip other than to be around each other for a week and revisit one of our favorite places on Earth: the city with the dorm where I met Evan and Paul in 1999. Two guys who liked Zelda and beer and lived a few doors down from me on the second floor.

Shortly after the trip, we started talking about putting together a 2024 calendar of our A.I. artwork—a way to literally pass the year together. This was after we’d visited the used bookstore and the pizza place where we ate a hundred times; after we’d looked in from the road at the restaurant that took the place of our favorite dive bar; and after Paul had had one last beer for the road, and decided to give up eating and take liquid nourishment through a tube.

The calendar would be a piece of physical media that the three of us could share throughout the year. But it didn’t escape me that it would also illustrate and amplify our remaining time together, however long—each square celebrating that Paul was still here and a helpless reminder that his days were numbered.

After Evan pushed Paul to his gate at St. Louis Lambert International Airport and we said goodbye, we texted each other later that evening to reiterate to Paul that we loved him.

Our Midjourney 2024 calendar is full of strange creatures and comedic scenes. We began last January with an image called “Tension at the Golden Corral buffet.” “BeefTeeth Bill comes alive” was our image for March. “The California Puke Boiz,” June. “Bob Ross painting the devil” stared at us through the famous artist’s now-possessed eyes and smile throughout October. We put images in for specific days. For example, Insect Appreciation Day depicts “Caterpillar-thing abomination, wearing a suit”; on 4/20, “Teddy bear in sunglasses lost in the haze of weed smoke.”

Evan and I visited Paul again this past December, and it was a sobering trip. He can no longer breathe on his own, and three months ago he had emergency surgery to insert a plastic trach into his throat. I learned how to inject different kinds of medication into Paul’s stomach tube and use a type of dentistry device to suction the spittle accumulating in his mouth. We watched as Melanie showed us how to get his trach to stimulate in his chest the mechanics of a cough. She moved his useless limbs around to get his blood flowing and rubbed them with lotion and creams.

He can no longer move anything but his eyes, his head (a little), and a few fingers on his left hand that navigate the mouse he uses to communicate with us, and to text. We helped Melanie clean his backside. We helped change his sheets and lift him into his wheelchair. We situated his head and feet on pillows and used tissues to wipe his eyes when he was in pain. An onslaught of indignities for him, but I felt grateful for any small opportunity to assist him and Melanie. To not simply feel helpless, and hopeless.

But the trip also had its moments of joy—the kind that Paul always wants to provide no matter what. We were three middle-aged guys sitting near one another in the warm house with a little decorated Christmas tree, listening to music, Paul watching as we played games, trying to make his family laugh by saying things like “Siri, play ‘I Pooped on Santa’s Lap’ by the Toilet Bowl Cleaners!” and tinkering all day with A.I.

We made a new calendar for 2025 and have plans for what could be our magnum opus: a coffee-table book. I could probably never argue in favor of what the technology of artificial intelligence might ultimately bring, its future implications for artists and writers and culture itself. It does scare me. But I also know that it made my friend Paul, who has ALS, laugh his ass off.