The best Milwaukee dive bars keep the city’s history alive

Naming “the best” dive bar in Milwaukee is an impossible task. Even listing five of them isn’t easy. In a city with as much history as ours — and the longstanding drinking culture to go with it — there’s bound to be a bar on nearly every corner that someone has called their favorite.

Heck, even defining what a dive bar is is tricky. For me, it’s a spot that’s been open for at least 20 years (in a building whose tavern history goes back decades). It seems a little sketchy on the outside but is friendly once you grab a barstool. Inside, there’s wood paneling, carpeted floors and loads of decor littering the walls. Strands of Christmas lights bring the ambiance, as does the sound of some random movie playing on cable on a mounted TV. To eat? Popcorn. Or maybe a pickled egg from that jar behind the bar. How long has it been there? Don’t ask.

The daily special is a beer and a shot and you’ll be paying for both with cash only. It opens at noon (or, even better, at 6 a.m.) and no matter how many times you come in or what time of day it is, that same guy is always at his corner spot at the bar.

Some owners may shudder that their bar’s called a dive. But to me, with a deluge of new spaces opening that are short on character and long on drink lists, it’s a term of respect, a badge of honor earned after years of long shifts, transformed neighborhoods and changes in taste.

These iconic Milwaukee dive bars fit the bill, and remain beloved for never changing what they are after all these years.

Jamo’s  

1800 N. Arlington Place, (414) 276-7101 

There’s only one TV at Jamo’s bar and guests all gather around. On Sundays for Packers games, sure, but it’s the weekday tradition more than 20 years strong that draws a crowd of voracious viewers: “Jeopardy!” at Jamo’s is a can’t-miss.

Owner Jamison Goll opened Jamo’s in 2002, and its time as a tavern dates back to 1890, but a stint in this bar feels like time-traveling back to the 1950s — right down to the mechanical cash register used to collect patrons’ dollars at this cozy, cash-only joint on Milwaukee’s east side.

The small bar is surrounded by wood paneling, multicolored Christmas lights, kitschy framed art and cushy booths. There’s deer taxidermy festooned with tinsel and paintings of buxom babes you can just make out in the comfortable darkness of the room. What you won’t find is a neon light with some beer logo blinding you as you sip on a glass or bottle. Don’t ask for a canned drink, though — Jamo’s pours everything into glasses. It’s a dive, but it still has class.

The Uptowner  

1032 E. Center St., (414) 702-6798 

This Riverwest neighborhood corner haunt claims it’s the longest continuously operating tavern in the city. It began as a Schlitz tied house in 1884, had a stint as a drugstore (that may or may have not sold booze on the sly) during Prohibition, and became The Uptowner in 1950.

It may be an oldie, but it’s not slowing down anytime soon. Sunday karaoke, live music rocking at the back of the room, and a colorful cast of regulars keep the space lively from noon to 2 a.m. daily.

Aside from its age, The Uptowner has a few distinct traits that make it a dive-bar delight: a vending machine that doles out cigarettes, lighters and Zyn packs alongside bags of Skittles and Doritos; a seemingly random sink hanging just outside the men’s restroom (no space inside to wash those hands); and a giant sign hanging above the bar indicating that the business is cash only.

Wolski’s 

1836 N. Pulaski St., (414) 276-8130 

You may be familiar with this legendary Milwaukee tavern without ever having stepped inside. Its famous “I Closed Wolski’s” sticker has been slapped on bumpers, bathrooms stalls and back bars across the globe and is almost as ubiquitous a sight in local watering holes as a Miller Lite tap handle.

The sticker’s been around for 50-plus years, but the bar has been in business since 1908, when Bernard Wolski first opened its doors. Bernard’s great-grandsons Bernie and Dennis Bondar keep it running today (their brother Michael, who created the “I Closed Wolski’s” sticker, passed away in September), still issuing its white-and-blue calling card to patrons who party there until bar close each night.

As far as dives go — especially considering its age — Wolski’s is pretty spiffy. Its wood paneled, green-trimmed walls gleam — as does the brass rail that stretches the length of the bar. But the dive-y touchstones are there: that rust-stained sink outside of the bathroom, faint sunlight barely brightening the room, a generations-old cash register behind the bar.

It’s entertaining enough just to take in the history of the place or chat with any of the bar-goers aged somewhere between 21 to 92, but if you get antsy, there’s billiards and free metal-tipped darts with Wolski’s-branded chalk scoreboards in the back. Or pass the time identifying the world flags hung from the ceiling.

Even if you don’t close Wolski’s, a trip to Milwaukee isn’t complete until you tip one back in this timeless tavern.

Y-NOT II 

706 E Lyon St., (414) 347-9972  

It’s difficult to know where to fix your eyes first at this beloved east side bar. The massive stock of mini, nip-sized liquor bottles behind the bar? The very same sized liquor bottles dangling from the ceiling like Christmas lights? The blazing neons? The barbershop chair? The dentist’s chair? The velvet John Wayne painting near the back?

They’re all part of what gives Y-NOT II its unique charm in a city with so many dive bars loaded with personality.

Tony DePalma (read his first name backwards to see how his bar got its name) opened the second of his three eponymous taverns in 1971, and it’s the only one still standing today. There, patrons throw back beers by the schooner (a large goblet), liter and half-liter. They mix their own drinks with bottled seltzer and two mini booze bottles of choice. They grab a seat at the long bar or settle into a beat-up booth or lounge chair perched on furniture dollies (so they can roll). They serve themselves baskets of some of the saltiest popcorn to touch your tongue.

What makes the space even more intoxicating is its 6 a.m. opening time. Well, technically, that’s when sister bar Coffeetails, connected to Y-Not with its own entrance around the corner, welcomes its first customers. It’s a haven for third-shifters thirsty for a sip. And if they stick around till 11 a.m., Coffeetails closes and the party moves upstairs to the hodge-podge haven of Y-Not II.

Zad’s 

438 S. Second St., (414) 271-9130

It’s rare to catch the “open” sign go dark at this Walker’s Point joint.

“You can’t drink all day if you don’t start in the morning,” reads a Zad’s T-shirt for sale behind the bar. It’s in reference to the tavern’s daily 6 a.m. opening time, with 20 hours of bar dice, pool-playing, dart throwing and pull-tab-ripping until it all shuts down at 2 a.m.

Those are all signatures of a good Milwaukee dive bar, as is the soundtrack of local radio (commercials and all), plus the slew of regulars on their perches at the long bar at all hours and the friendly bartenders who offer a giant “hello” and “goodbye” as you come in and out — regular or not. There’s something extra charming, too, about a low-key spot that sticks to its roots. On a stretch of Second Street that’s getting more polished by the week (and is home to some of the city’s most well-regarded restaurants), Zad’s is a scruffy-but-sweet mainstay that harkens back to the neighborhood’s industrial heritage.

This article originally appeared on Milwaukee Journal Sentinel: The best Milwaukee dive bars keep the city’s history alive

Reporting by Rachel Bernhard, Milwaukee Journal Sentinel / Milwaukee Journal Sentinel

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