First Look: Jerry’s Pizza, the Chicago Tavern-Style Pizza Instagram Sensation Turned Dive Bar Brick-and-Mortar

Jerry Benedetto brings square-cut, thin-crust pizza pies to Portland’s Bear Paw Inn.

By Jordan Michelman April 22, 2021

A Chicago-style square-cut, tavern-style pizza from Jerry Benedetto.

When does a pizza become something more? 

For Jerry Benedetto, the founder, pizzaiolo, and namesake of Jerry’s Pizza—tentatively scheduled to open to the public May 17 inside the Bear Paw Inn—the moment came late one evening in 2020. “This person reached out to me, and shared that their mother was in hospice,” he recalls. “She was from Chicago, and just really wanted to enjoy some Chicago style pizza.” By this time, Jerry’s was already a word-of-mouth sensation, a social media hit with a 1,000-person waitlist and pilgrimage-making fans from across the West Coast. Jerry obliged; one of his achingly, almost confessionally authentic thin-crust toppings-under-mozzarella sweet sauce tavern-style Chicago dive bar pies was delivered ASAP. “She wrote me back the next day—'I haven’t seen my mother eat this much in years! She started telling me all these stories I’d never heard from her childhood!’—and two weeks later she passed away.”

“I was just like, wow, fuck,” Benedetto mutters. “This thing, this food, it’s something bigger.”

He’s not wrong. As the kids say, where’s the lie? Benedetto, 33 years old, is originally from the Chicago area, a fact undeniably evident from his “Da Bears'' accent and vintage Chicago sports fits. He moved to Portland in 2019 alongside his fiancé: she’s a global communications manager at Nike, while he’s worked variously in the fields of beer and cannabis. Locked down at the dawn of the pandemic and deeply homesick, Benedetto set out to create a pizza pie in his home oven in a similar style to that which is served at taverns, corner bars, and Little League pizza pubs across Illinois and Wisconsin. It was a hit, with 8,000 Instagram followers and counting. What began as a social media sensation in 2020 with a fundraising and social justice mission (supporting organizations like My Block, My Hood, My City) is now preparing to transition into a full-fledged pizza operation in the spring.

Benedetto in the kitchen at the Bear Paw Inn.

Tavern style pizza is different from thin crust, and very different from deep dish,” Benedetto explains over a stunning pie he calls “The Works,” a vividly neo-classical expression of modern artisan pizza laden with sausage, pepperoni, onion, green pepper, black olive, and mushroom. “It needs to be thin and crispy, with a square cut, and cornmeal on the bottom.” Inspiration comes from legendary mid-century Chicago pizza joints like Vito & Nick’s, Barnaby’s, and Villa Nova Pizzeria, each of which Benedetto visited on a “tavern tour” to research styles across the city, stopping at 20 different pizza spots in five days.

Jerry’s Pizza bears approximately zero resemblance to the “deep dish” pizza trope that Portlanders might more commonly associate with Chicago. “Deep dish pizza is good,” Benedetto says smiling—or maybe smirking—from behind the ‘stache. “It’s something Chicagoans usually only have when someone comes in from out of town.” (Upon reflection, I’m choosing to interpret this statement as sort of the Chicago version of a Southerner saying, “Bless your heart.”) Deep dish might get the big chain store hype and Food Network TV specials, but tavern style is the pie of the people, and in Benedetto’s hands, the results are extraordinary.

Classic midwestern toppings are the focus: Benedetto makes his own fennel-studded sausage and uses Ezzo brand pepperoni (famous for forming “cups” during the baking process) offset by black olives, mushrooms, raw onion, and green pepper. His house red sauce is slightly sweeter than, say, a Neapolitan or New Haven style pie, but it is a deep, redolent, earned sweetness, framed by the saltiness of the cured meats and cheese. The scratch-made pizza crust is crunchy, a varied textural marvel that eats completely differently depending on where you grab a slice, from the crispy outer edges to the soft, pliant interior cuts, kissed with a thin layer of Wisconsin mozzarella. It is endlessly moreish; you find yourself forever reaching for another slice, no more than a few bites in size, and marveling at the interplay of salt, sweet, and crunch.

Pies start at $18, with additional veggies for $2, and meats for $3. Jerry will serve his pies for takeout and dine-in (with limited indoor and expansive outdoor seating) between 4 and 8pm Monday through Thursday to start, with “pizza puffs”—a sort of deep-fried calzone popular in Chicago bars—available to order from the bar at all hours. 

My favorite part of this pizza is the cornmeal. “I’m pretty heavy on the cornmeal,” Benedetto says, sharing that this style is directly influenced by the aforementioned Vito & Nick’s. The pie itself is already thin and crispy, but the cornmeal provides a second layer of crunchy complexity—a polyphonic meta-crunch, symphonized with savory sweetness, best washed down with an RC Cola or light lager by the pitcher. There’s nothing else quite like it in Portland, and by Benedetto’s estimation—informed by ardent online fans—Chicago tavern style pizza is almost entirely unrepresented not just in Oregon, but across the West Coast. “I want to offer Midwesterners a taste of home, yes,” he says, “but at the same time give Pacific Northwesterners something new. That’s the goal.”

Benedetto talks pizza at the Bear Paw Inn.

Benedetto has recreated the Chicago thin pie of his youth, but to complete the package he needed to find the right venue. The “tavern” part of tavern style pizza is no simulacrum; this pizza style is born from the bar, very much in the same American foodway traditions of the Buffalo wing or New Orleans broiled oyster. Communal enjoyment and co-imbibing is implicitly part of the experience, and to achieve this, he’s partnered with an existing dive bar, the Bear Paw Inn, just a block off SE Powell in the Brooklyn neighborhood. It’s a nothing-fancy room with plenty of beer taps, ample indoor and outdoor seating, and decades of accrued tavern vibe, which makes it perfect for Jerry’s Pizza. Inside the bar’s tiny makeshift one-man pizza kitchen, Benedetto plans to make around 20 pies a day to start, with a target capacity of 40 a day.

“I’ve had lots of people say I should do a food cart, or hook up with a restaurant group, but this pizza doesn’t make sense in that context,” he says. “It needs a room like this”—with a wave of his hand Benedetto points at the TV screen showing high school basketball, the pool tables, the brewery merch—“where the game is on, we’re having a light lager, eating some pizza, bellying up to the bar, saying hello to a stranger. It’s communal, like the square cut pizza is meant to share. A napkin, a beer, a slice, put your phone away, bring your family. That’s what this is, and I think people are hungry for it.

The arc is irresistible: the Instagram sensation pizza maker with a miles-long digital waitlist opening an explicitly analog, old school, 20th-century expression of Chicago family tavern pizza culture. The evocative, Proustian power of his pies will be available here exclusively, via direct order—Benedetto says he has no plans to partner with third-party delivery apps. The social consciousness of the pizza place as a hub for community advocacy is something he feels deeply, and shares with like-minded local pizza makers, counting local favorites Apizza Scholls, Scottie’s Pizza, and Pizza Doughnais (temporarily closing at the end of April) as early supporters.

Whether you grew up loving this pizza style or are trying it for the first time, Jerry Benedetto is offering Portland something worthy of that most 2021 of feelings: cautious optimism. The foods we love to eat express a sense of self, of culture, evoke wider resonances, mean something. Benedetto nearly said it himself at the end of our beer and slices, with just a few center cuts, little piles of cornmeal scattered across the pan like sand in a Zen garden.

“I have never considered myself artistic, or like an artist or anything, but making a pizza ... well, it’s really weird, man, I don’t know...”

Allow me to finish the sentence for him: Jerry Benedetto is an artist, and Jerry’s Pizza is art.

Jerry’s Pizza, tentatively opening May 17 at the Bear Paw Inn, 3237 SE Milwaukie Ave; open Monday-Thursday 4-8 p.m.; outdoor dining, indoor dining, and takeout available; on Instagram @jerryspizzapdx

Filed under
Show Comments