Maybe it will happen today, one Chicago pessimist hopes. Thousands of fans do too.

It was March of 2025, and everything sucked. Finances had been tough for a few years for Chicago artist Phineas X. Jones, 53, and he was deeply troubled by the reelection of President Donald Trump. Even so, the times planted a seed for him. In spite of it all, Jones doodled some flowers and sunshine and happy little animals on his iPad, framing a monumental set of words: Maybe it will happen today.

“I’m kind of on the pessimistic side anyway, so ‘maybe it could happen today’ is as optimistic as I get,” he said. “It’s possible a good thing could happen. I won’t rule it out.”

He posted the image on Bluesky, a social media platform for people who miss the old Twitter. Then he just kept drawing: the same phrase, in endlessly different contexts. Jones has rendered the words as a page from an illuminated manuscript, alongside Pinhead from the “Hellraiser” series, as an unfinished “Wheel of Fortune” board, in an Federal Art Project-style woodcut, in homage to René Magritte’s surrealism. More than 200 variations on a theme later, Jones has amassed some 12,000 followers.

Candace Dane Chambers/Sun-Times

On Oct. 22, he launched a Kickstarter offering a 2027 calendar, with stickers and prints as extra perks; the campaign — running through Thursday morning — was funded within hours and has raised more than five times its original goal.

Jones doesn’t self-promote, other than by staying consistent with his posting. His only focus as an artist, he says, is the vibe, a particular balance of hope with exasperation or frustration. “It” should never be specific, although fans of the drawings tend to respond as though it were. Furthermore, the process should not stress him out. Jones doesn’t plan his drawings or solicit requests. His standard is “it looks cool, and it was fun to draw.”

For such a hopeful conceit, Jones often returns to villains in the project. Sho’nuff from “The Last Dragon” blazes with the words, while Tim Curry’s towering red devil Darkness from “Legend” cackles beside it. Nosferatu (2024) looms beneath it, and Sideshow Bob threatens Bart Simpson with — what else? — a belly tattoo. It’s not all about bad guys, though. Jones is just as likely to enlist Max Headroom, Paddington Bear or a Chicago paletero as messengers.

A digital illustration based on a shoulders-up portrait photo of Little Richard from one of his early album covers. | Provided/Artwork by Phineas X. Jones

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The artist Patrick Nagel created one of Patrick Jones’ favorite illustrative styles. | Provided/Artwork by Phineas X. Jones

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A paletero with a white mustache wearing a sun hat pushes an ice cream cart with bells hanging from the handle. | Provided/Artwork by Phineas X. Jones

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The Hilton Sisters, Daisy and Violet, were well-known entertainers in the 1920s and ‘30s. | Provided/Artwork by Phineas X. Jones

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The original “Maybe It Will Happen Today” illustration, posted on March 20, 2025. | Provided/Artwork by Phineas X. Jones

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This city may have been primed to love his work. For a decade, Jones illustrated labels for Half Acre Beer Co., and he’s also designed screen-printed posters for bands and other brands. Although he’s a native of Fort Collins, Colorado, Jones has connected deeply with Chicago for the better part of three decades. Some of his other art includes what he calls “hot dog monsters” with a genealogy hinting at the Superdawg statues atop the famous Norwood Park stand. One of his most popular prints depicts pigeons atop the sign at the Belmont Red-Brown-Purple lines train platform.

The breadth of Jones’ influences, spanning both ancient Egyptian papyrus and remixed “Nancy” comics, is part of the project’s delight, in addition to his grasp of so many different mediums and styles. Jones demurs: “I wouldn’t claim to be a master of anything, but I like doing all kinds of different stuff,” he said. “I’m pretty good at copying, so I can pick up a style off of something or somebody else.”

Not a single pixel of “Maybe It Will Happen Today” or any of Jones’ other art comes from artificial intelligence, he says. The suggestion is offensive to him; he includes information on his source material in replies and alt texts on his posts. The vast majority of his images are hand-drawn in Procreate, digital illustration software for the iPad; any outliers are usually photomanipulations, also made by hand.

“[AI is] all stolen work,” Jones said. “It looks bad. It’s boring and same-y. And every time you use it, you’re making an evil person more powerful.”

Provided/Artwork by Phineas X. Jones

This deliberately low-tech and defiantly human approach has won Jones and “Maybe It Will Happen Today” thousands of fans. He tries not to let it get to him. As an artist, the pleasure of the project is in the process. “I can do whatever I want to, and however it turns out, that’s what it is,” he said. “I can’t get in trouble for it. Nobody gets to say I did it wrong.”

Perhaps someday, Jones muses, the appeal will fade or he’ll start looking like a tryhard. But his art is small-D democratic — deliberately accessible and absolutely something anybody can try for themselves. If anything, Jones’ work suggests the good thing that happens today might be someone stepping away from a chatbot prompt and picking up some art supplies. Whatever someone’s “it” happens to be, you can never rule it out.