John Calipari, Bill Conway and the Pope walk into a bar….it sounds like the start to a joke but as we found out at our return to Benny’s a similar situation did in fact occur. We had not been to Benny’s in over two years, on the previous trip the general consensus was that it was good but expensive. Years later would a similar theme emerge?

Crenshaw, Brad and myself decided to get an early start to the evening and met at the bar at 6:30. The bar layout is nice, there is a long bar and a number of tables. The jazz like live music added to the atmosphere, providing a nice background soundscape that never overpowered the room or became too loud. It wasn’t particularly crowded would be the only negative. Mason, Conway, Hans and special guest Roddy joined us and we were off and running.

We had a nice circular table and since there were only 7 of us there was plenty of room. The dining room had a number of tables filled but was far from packed. I placed an order for apps immediately: Maple Glazed Bacon, Shrimp Dejonghe and Calamari. The bacon was fantastic, the maple adding a nice element of sweetness and the bacon itself pork belly like. The shrimp was good but the reigning king of shrimp dejonghe is still Joe’s. The calamari was nothing special and fairly generic as far as being prepared in the standard way but anything fried is good so no real complaints.

I went with the dry aged bone in ribeye which was good, however I tried Brad’s wet aged boneless ribeye and it had better flavor. Sides were mashed potatoes, mac & cheese, creamed spinach and homemade gnocchi with mushrooms. The gnocchi was the highlight, first because it’s a unique option for a side and second because it was just bursting with flavor. For dessert there was s’mores cheesecake, which was unexpected in how it was served but tasty. There was also some type of chocolate cake which I don’t remember because it wasn’t that memorable. I thought the server was solid, he was attentive but not pushy.

As we all know I’m not a wine guy so I passed off my host wine picking duties. Crenshaw, Brad and Mason all diligently looked for a decent priced option and must like hot girls at the Horseshoe Casino there are just none available. Around $200 a bottle really the only option. That is ridiculous and I feel like its kind of shady too, knowing full well no one is going to leave once sitting. I see no reason why you can’t have a couple of reasonably priced options on the wine menu just like every other restaurant in the city. This holding the customer hostage via the wine menu just left a bad taste in my mouth, it’s the principal of the whole thing that doesn’t sit well.

Dinner conversation focused on the recent election for Mayor, March Madness, being in a room with Calipari and the Pope and getting headshots of Scotty Martin plastered on restaurant walls across the greater Chicago area. We also found out that Crenshaw is the Daniel Day Lewis of Steak Night, very quietly getting everyone’s attention like he has a serious announcement only to make fun of Hans for having two pairs of crocs, Oscar worthy performance. Roddy won credit card roulette because his card is made of steel and was too heavy for the waitress to pick up. It was my Birthday.

Benny’s is still good but expensive. It was one of the first steak houses to have steaks in the $60s but that is not uncommon now. However their wine list is their down fall and why they continue to be grossly overpriced. It’s good but not worth the money until they address their wine list.

After dinner drinks were at Snickers. Great evening as always.

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