Prosperity Social Club has been a part of Tremont for over ten years, but the bar itself has been in existence since 1938. Formally known as Dempsey’s Oasis, which is also the name Patrick Dempsey’s hot tub, it has retained much of its original character even as it acquired new ownership.
Prosperity Social Club is hard to describe because it is so many disparate things. At first, from the outside, it’s giving me Boo Radley’s house. It’s giving me thank God you have a sign advertising brunch on the outside because otherwise I would think my GPS was lying to me about your true location. It’s giving me 1970s castle realness.
Once I open the enormous door to step inside it’s giving me record scratch everyone at the bar staring at you for a beat in silence and then going back to their drinks and the music resumes. It’s giving me seat yourself. It’s giving me NORM! It’s giving me 24/7 Lo-Fi Instagram filter. It’s giving me Rosie the Riveter on a Tinder date. It’s giving me we serve the finest craft beers in the land. It’s giving me wood paneling realness. It’s giving me pin-up girl sleeve tattoos. It’s giving me gentlemen’s cave circa 1942. It’s giving me unironic polka party. It’s giving me Great Depression era Chuck E Cheese. It’s giving me #1 Uber drop off spot at 1PM on a Sunday. It’s giving me that one Gap commercial where people swing dance in khakis.
It’s giving me grandpa’s basement. It’s giving me over a dozen men named Hank spent more time sitting at this bar than they did with their children. It’s giving me a shot and a beer with a raw egg cracked in it. It’s giving me empanadas that should not be here but they are here and they are delicious. It’s giving me Dr. Sam Beckett stepped into the Quantum Leap accelerator and woke up to find himself trapped in the past. It’s giving me bootlegger daydreams. It’s giving me old school beer sign museum. It’s giving me $12 entrée realness. It’s giving me shouldn’t you go home now Earl no I’ll say when it’s time to go home goddammit. It’s giving me pierogies that are so good they hurt your Polish grandmother’s feelings. It’s giving me dust bowl Applebee’s. It’s giving me let’s all go to a thrift store after this. It’s giving me no, let’s stay and get another round in honor of our bad ass steel worker ancestors.
: For real, get the pierogies.
5 out of 5 feelings that you really should call your grandma and see if you can borrow her style.