On October 17, San Francisco’s City Hall will break from its usual business of budgets and zoning battles for something a bit offbeat.
Instead of arguing over square footage and tax codes, the Board of Supervisors will officially declare the city’s newest holiday: “Broke-Ass Stuart Day.”
For Stuart Schuffman—the writer, bon vivant, and longtime cultural troublemaker better known as Broke-Ass Stuart—the moment feels surreal.
“This is the culmination of my 21 years of creating meaningful work that celebrates the spirit of San Francisco and the Bay Area,” he tells 48 Hills.
It is a long way from the dive bars of the Mission District to a proclamation at City Hall. Still, in many ways, this is the only place the journey could end: a marriage of civic ceremony and the scrappy underground culture Schuffman has spent two decades chronicling.
The proclamation isn’t the only milestone. Schuffman is also releasing a 350-page retrospective, The Worst of Broke-Ass Stuart: 20 Years of Love, Death & Dive Bars, and celebrating with a launch party at Kilowatt on October 17.
Contrary to what he imagined, it wasn’t as easy as just pulling together old clips.
“I went back through nearly everything I’ve ever written—even old poetry notebooks and the drunken scribbles I email myself after a long night at Specs’,” says Schuffman. “I read through probably thousands of pieces, and I’m sure I even missed a few. What we ended up with was stuff that didn’t make me cringe when I read it.”
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The result is part memoir, part cultural archive, and part love letter to San Francisco. From his run for mayor, when he won over 20,000 votes, to globe-trotting adventures on someone else’s dime, to hosting his own IFC television show, Schuffman packs the book with escapades, heartbreaks, and essays that double as dispatches from the city’s frontlines.
“I call it ‘The Worst’ just so that, if you don’t like it, at least I warned you,” he says, with a laugh.
Schuffman is often called a modern-day Herb Caen, a comparison he doesn’t take lightly. The connection isn’t hard to see. Caen chronicled San Francisco’s quirks from the street level, and Stuart has done much the same, albeit with fewer martinis and more whiskey shots.
“I believe my work falls into the tradition of SF cultural chroniclers,” says Schuffman. “It’s a street-level attempt to examine both the heartwarming and heartbreaking aspects that make San Francisco, well, San Francisco—especially during a time of such cultural upheaval and soul-searching about who gets to decide the future of this place.”
If Schuffman’s early writing radiated honeymoon energy, the tech boom of the 2010s was a sobering wake-up call.
“Some of the early stuff, written before the tech boom of the 2010s, feels not necessarily like someone else wrote them, but more like someone in the limerence phase of a relationship,” he says. “I was so head over heels for SF that when things started to change, I was blindsided and given a rude awakening.”
He adds that the piece that feels most essential to who he is now is “I Didn’t Cry in the Bar When Trump Won This Time.” It’s the most recent clip he wrote for the book, and it does a good job of summarizing where we stand as a city and a nation right now.
Yet, despite heartbreak, Schuffman never packed his bags. San Francisco has given him both wounds and fuel, and his collection reflects that tension.
“It pinpoints a time and a place and holds it there for further examination,” says the author. “That way, those of us who lived through it can remember what we were going through, and those who weren’t there can know what it was like.”
At its heart, The Worst of Broke-Ass Stuart isn’t just about one man’s bar tabs and heartbreaks—it’s about a city fighting to retain its soul.
“How hard we all fought to save the city that we love,” Schuffman says. “We lost a lot of the time, but we also won a few times. And also, that a town will always continue to change, no matter how much you win or lose.”
The book serves as a reminder that San Francisco is more than just the latest boom cycle; it’s also about the protests, costumes, and cracked sidewalks that don’t make it into the real estate listings.
The idea of an official day started with a playful ask. Schuffman reached out to Supervisor Myrna Melgar and asked if the Board would consider declaring the day his retrospective comes out “Broke-Ass Stuart Day.” She was so tickled by the idea that she introduced it to the Board—and to Schuffman’s surprise, it was passed.
For the writer, the proclamation is about more than professional recognition. “My personal work and my community building are all tied together,” he says. “So, I think it’s a celebration of my writing and the way it’s impacted the people who read it.”
Naturally, “Broke-Ass Stuart Day” will come with a party—his book release celebration at Kilowatt in the Mission, thrown by his dear friend and badass event planner extraordinaire, Jenn Stokes of Stokes Live Entertainment.
The rest of the day will be more personal. “I’ll be coming off book tour dates in San Diego and LA, so I’ll be glad to wake up in my own bed,” says Schuffman. “Then I’ll probably get a nice brunch with my wife, and then work far too much, just like usual.”
After all this, what’s next for Broke-Ass Stuart? He says he’s working on some early-stage side projects as well as a screenplay.
And Schuffman isn’t abandoning the platform that made him a household name in San Francisco. “Most importantly, though, I’ll continue the work my team and I do at BrokeAssStuart.com, telling the stories we’ve been known for for decades now,” he says. “48 Hills readers can help us keep doing that by joining the Broke-Ass Stuart Patreon. We really need the support to stay afloat.”
If the day at City Hall and the book release underline anything, it’s that Schuffman’s relationship with San Francisco—like the best love affairs—is complicated, messy, and enduring. No matter how much the city has changed, he has no plans to leave it in the foreseeable future.
“There are definitely several meditations on that topic in the book,” he says. “But the most succinct answer I can give you for these purposes is: Where else am I gonna go? Despite all the fuckery, I love this town.”
And for at least one day in October, the city is seconding the emotion.
THE WORST OF BROKE-ASS STUART: 20 YEARS OF LOVE, DEATH & DIVE BARS Fri/17, 7pm. Kilowatt, SF. Tickets and more info here.
Order The Worst of Broke-Ass Stuart 20 Years of Love, Death, & Dive Bars here.
