Restaurant Review: Jerry’s Tavern Is Wise Beyond Its Years

I first met Jerry Benedetto in 2021, when his pandemic sensation Jerry’s Pizza took up residence in a Brooklyn neighborhood bar and won a monthslong wait list. Tavern-style pizza—crunchy, thin, square-cut—is a rarity outside Illinois and Wisconsin, and Jerry’s version was a pitch-perfect transplant, laden with giardiniera, sausage, and mozzarella imported from the Upper Midwest. But the pop-up was a stepping stone. At the time, Benedetto told me about his dream: a true family tavern, the kind of joint he grew up going to outside Chicago, with a generational patina of sports memorabilia on the walls and the psychic air of so many pitchers of lager and good times after Little League tournaments.

Such is the scene inside of Jerry’s Tavern, the bar and restaurant Benedetto opened off a bending corner of NW Nicolai last May. It looks like it opened in 1946 instead of 2024. There’s a Little League–ready orange Gatorade cooler on the counter and stacks of beer lining the floor with “this is just a bar” nonchalance. It’s dim, warm, maximalist. Ancient beer stuff is everywhere: Miller Lite and Old Style chandeliers salvaged from pubs back home, Blatz beer elk heads, old Sports Illustrated covers, including a couple of the ’70s Blazers. Classic rock is on the juke and the smell of fried cheese curds is in the air. “Whatcha up to this weekend?” the bartender asks me. “Do you work around here?”

Still, Benedetto calls it a work-in-progress. “I want us to know you,” he says, “your name, your drink, whether it’s your first time in or your hundredth.” These are lofty goals. But Benedetto is right that, however appropriately decorated, a bar of this sort is nothing without a steady cast of regulars. Thus far, Portland is leaning in.

Benedetto brought the same obsessive devotion that made Jerry’s Pizza famous to his tavern, except, notably, there’s no pizza. “The kitchen here is just too small,” he says, though he is plotting another place, and interviewing pizza chefs back home to perhaps make a move out here when the time comes. Because he’s a guy who got famous making pizza, the fact this place is a hit without it is sort of mind-boggling. But then you taste the fried cheese curds, a Wisconsin bar requirement. Jerry’s are puffy-crispy clouds of squeaky-gooey cheese sourced from his favorite Midwest creamery, hot and served with ranch. The wings are already stuff of legend, adjudicated our region’s finest by the PDX Wing Guys, a collective of drumstick enthusiasts who contributed to PoMo’s wing guide. Eating them is a polyphony of textures: the outer skin of dry-fried crunch, the silky slip of Frank’s RedHot cut with butter, the creamy chill of endlessly re-dunkable blue cheese. Look for a combination of drumsticks and flats, big but not too big, saucy but not sloppy. It’s no-fuss bar food, and yet wings this good demand a deeper intention. They’re simple but they’re not.   

You could draw a wider parallel between the cooking philosophy and the bar itself as a living entity: zero funny business; a textbook, reverent approach to regional classics with a faith that God is in the details. Wings and beers, that’s normal. But the superlative execution of what they do at Jerry’s is transportive. It’s a fantastic, created world, and that’s exactly the point.

Weekend specials like goulash and outdoor-grilled brats hint at a few directions the menu could take in coming months. My favorite so far are the mini burgers, a riff on the bar standard slider, which arrive soft and steamy—shades of Canard, by way of White Castle—with tons of shredded onion, pickles, and melty Muenster. Even the pub snack mix is worth mentioning: pretzels, Chex, magic dust. There’s homemade puppy chow, too, for a sweet tooth, or the kids. (Jerry’s is all-ages until 6pm or so; babies will be fussed over by staff and patrons.)

Oftentimes the bar at Jerry’s is terrifically busy, doubly so during big games. But the staff manages the neat trick of maintaining friendly, genuine hospitality against the side of thirsty punters—no QR codes or Resy reservations here. On a mellow afternoon, it’s another sort of divine: liminal, dreamlike, with Tom Petty and the Heartbreakers on the digital jukebox and $3 lagers from one of the oldest independent breweries in the country, Stevens Point in central Wisconsin, going down clean and smooth. Regulars are regular folks of all stripes, ages, backgrounds, and professional remits drinking a couple two, three drinks, watching games, and eating uncommonly good bar food. Hi-vis vests after work are a common sight.

The 750-square-foot tavern sports a handful of small booths and bar tables, and a mere dozen bar seats. Often, it’s a standing affair spilling onto the sidewalk patio, fit with an outdoor TV so no one misses the day’s game. While Jerry’s is not by definition a “sports bar,” the rhythm of fandom pulses throughout: Da Bears (Jerry’s team), the Packers (his wife Lauren Benedetto’s team), and the University of Wisconsin Badgers in winter; the Cubbies, the Brewers, and even the lowly White Sox in summer and fall. Seahawks fans, I can report, are viewed with friendly skepticism, and a Minnesota Vikings flag hanging indelicately above the men’s room john sends a loud-and-clear message (Editor’s note: the flag has since gone missing).

Impressively, and proudly, Jerry’s sells more Miller High Life than any bar in the region, but that doesn’t mean you should skip the cocktails. Wisconsin native Ranessa Williamson-Callen manages the bar, and serves drinks reminiscent of her days working at the Del-Bar, a central watering hole of the beautifully campy southern Wisconsin tourism hub, “the Dells.” If you’ve never had a proper Tom Collins, the fruit salad that is a Wisconsin old-fashioned, or a Jell-O shot of Malört, she can help. But the can’t-miss star here is Williamson-Callen’s impressive Bloody Mary: a 20-ingredient mix, lager back, and a skewer of summer sausage, Muenster, pickled onions, olives, and a whole pepperoncini. It’s the best Bloody Mary I’ve ever personally consumed in Portland, full stop, and an emblem of the perfected-classics ethos that guides Jerry’s Tavern.

Fans of Tulip Shop Tavern, Bellwether Bar, and other high-low Portland bars nailing the classics will find lots to love about Jerry’s, but its closest local peer is the Helvetia Tavern, a true-blue roadhouse with food worth the drive into Hillsboro’s deepest rural farmlands. I’m an easy mark for this sort of thing. Jerry’s reminds me of the working class taverns I hung around while growing up in Tacoma, and the corner bars I see visiting my older brother in Chicago’s Roscoe Village neighborhood. But Jerry’s is no simulacrum of the Midwest tavern. None of these tchotchkes came from a kit, or a venture capital group, or a branding team. The 1984 Cubs starting lineup poster, the old Marquette University pennant—the bar’s whole glorious crust of memorabilia was peeled from Jerry’s own childhood bedroom in Illinois, diligently saved by his mom.  

The working fella next to you at the bar is real, too. He’ll sigh deeply, slake a draught of his ale, and exclaim, to everyone and no one in particular, “It feels good to be off.”