Wood panelled walls, hoppy signage, and a kitchen slinging some delicious Eastern-European flavors till late. Sounds like heaven, right? That, or Prosperity Social Club, nestled in an unassuming brick building in Tremont.

“We like to say this is the ‘Clevelandest Bar in Cleveland.’ If you wanted to snap a picture and put it clearly in an encyclopedia, you could,” says Jeffrey Siefer, Director of Operations for Buildings & Food.

A Step Back Into Time

The building has lived many lives; there’s no doubt about that. Once a place called Hot Dog Bill, selling hot dogs and coffee from the front window, 1109 Starkweather Avenue has always been home to a hole-in-the-wall joint. Prosperity’s beginnings date back to 1938, when the original owner, Stanley Dembowski, purchased the building and surrounding properties to open Dempey’s Night Club.

The title "Night Club" was adopted to attract a diverse crowd, as women were not generally accepted in what society considered "bars" at the time. However, the atmosphere was lively, with the iconic Leisy beer on tap and a growing cult following around the establishment.

Nearly every member of the Dembowksi family had their hand in running the joint, which later was renamed to Dempsey’s Oasis Tavern to encourage a more casual crowd to hang around. Dempsey’s offered fishbowls of beer and wine (which you could purchase an egg for 5 cents to crack into it for some more “lead in their pencil”, according to Stanley’s son, Richard), and indulgent, classic bar snacks like pretzels and cheese corn.

The Dembowski family's legacy continues at Prosperity Social Club, even though the bar has changed ownership several times since their retirement. Previous owner Bonnie Flynn was committed to preserving as much of the bar's history as possible. Current owner Will Hollingsworth and his staff share this dedication to maintaining the heritage.

Irresistible Atmosphere

“We have our old-school crew that’s been with us for decades. They remember it here as Dempsey’s and love what we are doing with it now. We’re modernizing the selections, but not the space,” says Siefer.

We had the pleasure of visiting Prosperity Social Club on a Wednesday evening, greeted by their weekly Polka sound, played by Stan Mejac. The folks at the bar top were laughing over some inside joke, with more intimate tables of couples and friends nestled in the back of the space. Immediately, you can’t help but be entranced by all of the wall decor, trying to catch a glimpse of what might be your favorite and trying to distinguish precisely how old everything is.

“All of the signage and wood is original, not reproductions. Completely old-school, bought, and scrounged up at flea markets and garage sales. It’s the real deal, the wood is original,” says Siefer. “It’s kind of like a time warp, but the younger generations love it too.”

The bar's versatility makes it perfect for any occasion, whether a quick late-night drink, small bites with friends, or a post-Church lunch with family. And, of course, Prosperity is no stranger to the Friday night fish fry rushes during Lent.

“People sometimes think we only offer fish fry on either a Friday or during Lent, but we have fish fry on the menu every single day. So, if we’re open and the kitchen’s open, we’re serving fish– and a lot of it!”

Brew, Bites, and Beer-Battered Fish

“The Cleveland area and the surrounding suburbs have a big influence from Ukraine, Poland, and Hungary. That’s the way we lean with a lot of our best-selling dishes.”

You can’t be the “Clevelandest Bar in Cleveland” without serving up some fantastic Eastern-European food, but Prosperity Social Club’s got that covered. Some of the menu hits are classics like stuffed cabbage, served in both Hungarian and Polish style, and their pierogies, which can be ordered traditionally or fried.

“We always want to stand out from the crowd and be something that we think the neighborhood needs, and we also think that the neighborhood needs some reasonably priced stuff,” says Siefer. “So, we keep our kitchen open till midnight every day, except Sunday.”

^{You can't skip on the Vegan Fish Fry. It was a hit! (Courtesy of Eat Local Ohio)}

“The menu is a little bit of everything, but definitely leans towards an Eastern European flair.”

For those of us who are more indecisive, a menu with dishes inspired by various cuisines and cultures can be interesting to navigate. If you need somewhere to start, I’ve got you covered:

Starters:

-Potato Pancakes, served with apple-cranberry chutney and sour cream

-Fried Pepper Jack Triangles, served with raspberry aioli

Main:

-Paprikash Chicken Sandwich, breaded chicken breast with paprikash sauce, sweet slaw, pepper jack cheese, onion frizzles, and milk bun

-Prosperity Bowl, black beans, peppers, onions, slaw, pico de gallo, avocado, coconut-lime rice, with the option of chicken, tofu, or shrimp as protein

-Fish Fry, this classic beer-battered fish fry landed on the Travel Channel back in 2016

And the drink selection is just as premium as the food. Pick your poison from one of their extensive lists, whether you lean towards a cocktail or want a premium whiskey. Prosperity even has a beer brewed exclusively for them from Sibling Revelry Brewery, the “Gotta Haddock” Lager.

“We try not to be too full of ourselves, but we aren’t a dive bar, either,” says Siefer. “We’re not just here to sling $3 beer, but we’ve got that covered for you, if you want it. We are very anti-snobbery, but are here to offer the good stuff for the people that want it, as affordable as we can make it.”

Siefer laughs and urges anyone who hasn’t been to Prosperity since 2021 to come back and look behind the bar, as Prosperity’s alcohol offerings have grown tremendously. 

On the Horizon

The Buildings and Food staff always find small ways to elevate Prosperity while preserving much of the history. Prosperity is a fantastic spot to catch Karaoke on the first Monday of every month, live Polka music on Wednesday, and good times every other day.

“We don’t just want to stand on the tradition of the things that have made us popular up until now. We’re always exploring new things and, you know, we listen to the market,” says Siefer. “Vegans are a growing market, so we’ve introduced a vegan fish fry.”

On the horizon, you have to watch out for Dyngus Day offerings. This April 21st, Prosperity will open early and offer all-day live music, fantastic food, and an atmosphere you won’t want to miss

 

 

 

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Visit Prosperity Social Club!

1109 Starkweather Ave, Cleveland

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