Every time I am visiting my family in Wi I try and make it to this place! I love it! I have had some of my best memories there celebrating my Grams birthday when we shared the delicious banana cream pie, with my brother and sister recently for my sister's 50th birthday, sadly when my father passed away my love and I went there for a nice quiet dinner at the bar and the music that was playing my mom and dad would play on our stereo. Bittersweet. The decor is so cozy and pretty. Feels like home. The service and food are always absolutely perfect! Can't wait to go back and make more memories and have that delicious food! The bartenders are always fantastic! read more

A little on the pricey side, not a big menu selection. However the food was cooked properly, service was excellent and they don't charge a garbage fee for using credit cards. We went on a Thursday night and still needed to wait 40 minutes for a table. I didn't expect that since this place is a bit off the main corridor. I had been here several times, but my last visit was probably 8-10 years ago. I always forget about it since, like I said, it's off the Hales Corners corridor of Hwy 100, and a little too far east on Janesville Rd from main Muskego corridor. The place hasn't changed a bit on the inside. Still a semi-formal interior with plenty of seating in both the dining room and bar area. It can be a little loud when full, and having a conversation with my husband was quite difficult. That's a pretty typical experience in these older buildings though. Just something to keep in mind if you're looking for a quiet dinner location. I ordered salmon, my husband ordered a steak. We both had soup as a starter along with a relish tray and bread - both of which seem to be unlimited. I thought my salmon was cooked perfectly, though my mashed potatoes were watery tasting. My husband thought the same of his steak and potatoes. Not the worst thing in the world, but mashed potatoes are not hard to do properly so I was a little disappointed in that. Would I come here again? Probably. Our two dinners were more than $80 before tip, so it was an expensive night out. It's not a place we would add to our normal rotation, but it's a decent special occasion spot. read more

First time here , was recommended to us from some friends that live near Diamond Jim's Super neat super club environment and the servers and hosts were just outstanding ! My prime rib was perfect , great flavor and even so big had to take some Jo,e for Sunday dinner ! They also have Collaso Mushrooms for an appetizer ! OMG huge and so good ! They also have great deserts , home made for sure ! We had the banana pie , may I say one of the best I have ever had , I know many skip the desert , but if you go here maybe start out with desert first ! Over all fantastic and a big call out to our server who took great care of us and ensured we had a great first experience ! read more

See all

We had a great birthday dinner for my husband tonight! 6pm reservation and we were seated right away. Our waiter, Santo, was excellent at his job. Kind and approachable, you could tell he was a favorite of several regulars in the crowd. This is a classic supper club. Good quality, good price, relish tray, bread, salad, soup, prime rib, seafood. Our meals were excellent. The bar area was busy/loud and they had the Brewers game on. If you want a quieter experience, ask to sit on the non-bar side. No room for dessert, but we've heard great things about their banana cream pie. We were again the youngest people in attendance, but that's ok with us! Plenty of parking in the attached parking lots. read more

See all

Four of us had an early. 4:00 p m birthday dinner celebration, and it was mostly great, with one exception. None of us drink alcohol, so we were referred to, jokingly, as "big spenders", but in a friendly manner. The table was greeted with warm bread and butter, and a classic Wisconsin supper club relish tray. We each ordered something different, including baby back ribs, grilled Salmon, jumbo breaded shrimp and a surprise fish fry, which they serve every day and not just on Friday's. The shrimp was large, filling, and so juicy it seemed like lobster in butter. The ribs were bountiful, tasty and not overly sauced. The fish fry was very filling, so much so that one of us got to take one piece and a few leftover ribs home for a next day surf and turf. The only letdown, and sadly, it was the birthday girl's meal, was the salmon, which was overcooked, dry and lacking in flavor. Dessert was a strawberry schaum torte, so good one wanted to lick the plate. We thought it was a birthday treat on the house, because the bill was a little light, so I over tipped, only to find out it was a mistake and we had to pony up another ten bucks. No problem. When your whole group has no hard liquor drinkers, the fare is more than reasonable. read more

See all

Was able to get an 8:30 dinner reservation on New Year's Eve, but had to wait a bit for our table. We sat at the bar while we waited, and due to the crowd had to wait a bit for our order to be taken. When it was, the bartender seemed almost annoyed. He made little eye contact, did not smile or engage in any conversation. Once seated however, our server Sergio more than made up for that. He was very friendly, attentive and accommodating. Unfortunately, because of our late seating, there were some menu items that were no longer available. I wanted the 1/2 rack of ribs, but instead got the bacon wrapped scallops. They were served wonderfully hot, with the scallops being nice and flaky and the bacon adding a nice smokey flavor. The only down side was the amount of bacon fat they were sitting in. I also had the Lobster Bisque soup, which was creamy and a bit savory, but could have used some more lobster pieces. My husband had the Beer Battered Jumbo Shrimp, which came in massive pieces. There was a little too much breading on it for my liking, but he enjoyed it very much. We also started with the Colossal Mushrooms, one of the specials, which were very good. However, here too, a little too much breading for my taste. Diamond Jim's has a classic supper club feel, but with Italian decor. Quite interesting. A good experience overall. read more

See all

I literally drive 6 hours and think about the prime rib dinner the entire drive! Amazing prime rib, mushrooms, onion rings, baked potato and old fashioned! And DO NOT leave without having the banana cream pie!!!! The prime rib is so tender and flavorful!!! read more

Diamond Jim's Steakhouse - Prime rib, onion rings - Steakhouses Near Me - Hales Corners, Wisconsin

I had the tenderloin and lobster tail. It was amazing! In the past I normally get the prime rib because its so good and now its going to be hard to choose lol! Service was great, restaurant was full but still able to hear each other talk! read more

My party was celebrating a birthday on a Saturday night and it was a long night. We asked the hostess for the specials of the day and she said nonchalantly that she didn't know and asked us to check the board in the other room. Our server took our order after a little while and she kept coming back apologizing because there was an issue in the kitchen and the food was not ready after what felt like 45mins. And she was visibly stressed and mortified. The system was down, being the main problem that night. In spite of it, the food was great. It's an old-school supper club that seems to need some updates starting with their website (the latest post is from 2022). Their customer service needs improvement, as well. Their banana cream pie was the highlight of my Diamond Jim's experience. read more

See all

Recently got a gift card for the restaurant which haven't been in years. It is a smaller and quaint inside. Usually always busy with driving past and was busy when we went. The prices are on the upper range for the petite fillet which ok. You do get a relish tray, bread basket, and a salad or soup that is included. Got the fried chicken dinner, which was a lightly breaded and came out steaming hot. read more

See all

Friends have been telling me for awhile that I have to try this place for the Prime Rib, and I had a gift card so I thought why not tonight. When we got there, around 5, the parking lot seemed full, but we found a back lot which had ample parking. We were a party of 3 and. did not have a reservation, and expected to wait, but we were seated right away. The ambiance was that of a nice supper club, without the fuss. We felt very comfortable wearing jeans. The server came and took the cocktail orders right away, a Tito's and Sour for me and a Ketel One and Seltzer for my friend. My husband just had water, then the server left us alone for a few minutes to study the menu. We pretty much had our minds set on prime rib and didn't even bother to ask about the specials. I had the queen cut, cooked med rare, a twice baked potato and garden salad, and my friend had the same. Husband had the king cut, done med, regular baked potato with butter and. sour cream and a salad. Dinner came with a bread basket and relish tray. To end the night, we all shared one giant piece of banana cream pie. Seriously, don't wait for a special occasion to treat yourself. read more

See all

This is a cute little supper club with a variety of options. It took a while for our waitress to even acknowledge us but was super friendly with the tables that had regulars seated. The incorrect meals came to our table, and then we had to keep re-asking for items we needed. My seafood platter had cod, shrimp, and scallops. The cod was good, but the shrimp and scallops just didn't have great flavor. The ribeye I shared was cold (it was medium rare) but normally is a warmer temp. The group I was with had ribs and those were the crowd pleaser for value perception and flavor. The banana cream pie was the best part about the meal! The crust is delicious, bananas ripe, and put together well. read more

See all

Our dinner started off poorly when they lost our reservation. I understand it happens, but the hostess asked if we were sure we actually spoke to someone or just left a voicemail. In the latter scenario, wouldn't they have called back anyways? Our server was great and the food was good, but it took an incredibly long time to arrive (45+ minutes). It's also a bit more of a homey atmosphere, so it can be very difficult to have conversation at your table. read more

Nice supper club atmosphere and tasty food to match. It's close enough to Milwaukee to be considered locally convenient. Lively customer base and the waitstaff seems to recognize the local regulars. That's always welcoming. Lamb Chops and Prime Rib were nicely presented and well prepared on a busy Saturday evening. Phoned in during the week to make a reservation for two. Might be a good idea for weekends. Parking was a challenge for our less mobile diner. No ADA entrance was available. Steps to navigate. But kind strangers stepped in to assist. Much appreciated. Will return to enjoy another meal at this steakhouse. read more

Diamond Jim's Steakhouse - Lamb Chops - Steakhouses Near Me - Hales Corners, Wisconsin

See all

We went to Diamond Jim's last night; I'm hovering between a 2 and 3 but I'll go with the 3 as my husband truly enjoyed his medium rare queen cut prime rib dinner. He said it was cooked perfectly, and his baked potato was hot and fluffy. He had French onion soup, and said it was good. His only complaint was that he was never asked if he would like sour cream for his potato, but he was able to request and promptly receive it. I ordered split pea soup; good flavor. My entree choice was sautéed sea scallops in lemon and garlic and a side of green beans amandine (one almond). My scallops, while they looked gorgeous (yet only 4 scallops as opposed to the 6 most restaurants serve) were absolutely dreadful. They tasted as though they had been marinated in salt. My husband, who is usually a bit heavy-handed with the salt shaker, tried a bite and even he said it was incredibly salty. Our server, who was very nice, talked to the chef and reported back that the chef does not salt the scallops. Sorry, I beg to differ! She took my plate back to the kitchen; between us we had eaten 2 scallops. She returned shortly with a small dish with 2 more scallops. They were not salty, but slightly undercooked and not cleaned well of grit. But I was hungry and I ate them. The green beans were ok; the relish dish for both of us had 1 green onion, 1 radish, 2 tough and thick baby carrots, a green olive, 2 black olives, a pickle, and 3 pepperoncini. I know a relish tray is a supper club hallmark, but maybe this offering is past its prime here. The decor for a steakhouse was kind of strange; reminded us of being in an Italian restaurant with murals and Italian looking paintings, all interspersed with autumn decorations. Not criticizing; it was just not what you'd expect to see at a steakhouse/supper club. The service, however, from our primary server and a teen boy who kept water glasses full, bussed the table, and seemed to honestly care how we were doing was tremendous. Can't say enough about that! Because my husband enjoyed his meal so much, we may go back, but no scallops ever again! read more

My sister took me here for my birthday. The first thing that should have warned me was the fact that the menu had no warning that the restaurant wouldn't be responsible for steaks cooked over medium. I crossed my fingers and ordered a ribeye. I had upgraded to the French onion soup. My sister ordered the salmon. The complimentary relish tray arrived. Pretty sad-- dried out vegetables and not many of them. The bread wasn't warm, either. Soup was okay but very salty. Salad standard. But my steak.-- It was tougher than the proverbial shoe leather. When I pointed it out to the waitress, she said she'd get the manager. The manager, a woman, came over. I explained that my steak was not edible and she said that was because my steak wasn't cooked well enough. What? Yes! I said, What? and she started shouting that "Everyone knows that the more you cook meat, the more tender it gets." I was so embarrassed, I wanted to crawl under the table. She didn't even offer me a different steak, or dessert, or anything. All she did was take the cost of the steak off the bill. I'm NEVER going back, and I've told everyone I know to avoid Diamond Jim's! read more

First timers. Very busy Saturday night. Tony bartender was great. Devon our server was fantastic. Salad and French onion soup just okay, but prime rib and steak sandwich made up for that. We'll be back! read more

Diamond Jim's Steakhouse - King cut prime rib! - Steakhouses Near Me - Hales Corners, Wisconsin

See all

Walleye fillets VERY fishy. Perch was good. Not great. Fries were subpar and limp. Ambience and service great. They have some work to do in the food. read more

First things first, I ordered fried shrimp as an appetizer and I expected it to look like a hook but it came out as butterfly shrimp. The food was mid. Lot of people too good bread though read more

Diamond Jim's Steakhouse - Steakhouses Near Me - Hales Corners, Wisconsin

Food was average at best. Our waitress, probably a high school student was nice but she had no clue. 3 of the 4 people in our party ordered soup, she brought it after she brought our dinners. She gave me my salad to go after we finished eating. Our water was never refilled and she never asked if we wanted another cocktail or soda. Also, we didn't get a relish tray or bread. No way were these meals worth $190. We won't be back. read more

Love the homey feel walking into Diamond Jim's! We took a chance & just walked in without reservations. We were warmly greeted with a no problem, have a seat at the bar. We quickly found a couple of open chairs, ordered a cocktail. Within an hour, we were seated at a table with a bread basket & relish tray. Our server was attentive & checked on us often. I ordered the filet & bacon wrapped scallops meal & it was delightful! Everything cooked to perfection. Highly recommend this neighborhood supper club! read more

Diamond Jim's Steakhouse - Filet, bacon wrapped scallops, loaded baked potato - Steakhouses Near Me - Hales Corners, Wisconsin

I have been craving prime rib for a long time so I stopped here at 4:45 on a Saturday and it was just about full and 20 minutes later it was bar only to get a table to wait or eat at the bar. By the time I left the bar was packed like sardines. I started with an old fashioned the traditional Wi supper club drink of choice, bourbon sour which was very good and refreshing. The menu doesn't list size for the prime rib, just king or queen so I opted for the $40 king not expecting anything big compared to other are steak house prices which are more. Service was pretty decent for how packed they were and my food was hitting my table pretty quickly. The relish tray and bread were sent back because I could even finish my dinner to start with. The prime rib dinner comes with 2 sides and I chose mashed potatoes and French onion soup. The baked French onion soup looked good with plenty of onions and croutons topped with melty cheese. The baked French onion soup was average and the broth lacked depth compared to the better ones out there but still hit the spot because I'm a sucker for baked French onion soup. The prime rib looked amazing and probably 16 ounces if I had to guess and thick, not super fatty like some places. The prime rib was melt in your mouth amazing but the bark was over seasoned because it was super salty but I like salt. The mash potatoes didn't have gravy but like a clarified butter which was delicious with a thick texture, no watery mashed potatoes. Overall my prime rib dinner was delicious and at the $40 price point and probably the best deal in town for a steakhouse because I was expecting at least $50 with all the fixings. I would definitely recommend the prime rib dinner. read more

See all

True supper club vibe. I've been coming here for many years. Never disappointed! When I'm in a rush, I can call ahead and enjoy a carry-out. Their entire menu is available for carry-out; and their pick up time is always spot on. Shout out to Sue and staff for their commitment to great service and food! read more

Great service and perfectly cooked steaks. Price is worth the service and food. Did not need a reservation and the wait time for table was about 15 minutes. Parking in front and in the rear of the restaurant was a good plus. read more

We went here the other night to celebrate our anniversary dinner. I love supper clubs and I really wanted to like this place but I just don't think I would make the drive to come back. I gave it 4 stars because somethings that made our experience less then desirable were not their fault, such as the group of six that were seated right next to us that appeared to be in extremely intoxicated and yelled everything they said acting as though they were the only table in the restaurant. That made the whole experience just plain suck right off the bat especially because they remained through the whole meal and we were trying to celebrate a relatively quieter kid free evening. I ordered the lobster and filet. The lobster was huge!! The whole dinner could have been shared with someone else. The butter for the lobster was weird almost tangy. I'm not sure it was real butter but that was a bummer because it made the lobster taste weird. We were also disappointed that the drinks were not very good. My husbands old fashioned tasted like cinnamon soda and my bourbon sour wasn't very sour. I did like that dinner was served with a relish tray and bread. You also had a choice of soup, one being baked French onion which came with the dinner, it was not served ala carte like at other steakhouses. They do have a sign on the door like most businesses lately stating they are short staffed. I did not find the service a problem. Briar was our server and he did fine as far as his job but wasn't very personable or crack much of a smile. Maybe that large table that was his was also driving him crazy ‍ read more

Diamond Jim's Steakhouse - Filet and lobster - Steakhouses Near Me - Hales Corners, Wisconsin

This place is super quaint and sort of a hidden gem in my opinion. Went there for my father-in-laws birthday dinner on a Saturday around 5:00pm. Made a reservation for four, for my husband and I and my in-laws. My husband, FIL, and I ordered one of their steaks, while my MIL opted for their fish. All of the food that came out was really tasty and cooked to almost perfection. I ordered mine medium rare and it was almost too rare, so just be weary that this is a place that will not overcook your order. Service was good. Total bill as about $300 including tip, which is about standard for four people. Will definitely return there again! read more

Great food ',,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, and the best banana cream pie freshly made order a piece before it's all gone!,,,,,,,,,,,,,,,,, read more

Very old school supper club feel. Crowd was older. Food was not as good as I expected. My pasta dish was overpowered by red pepper, the boyfriend's fish fry a bit bland. Old fashioned was yummy and the service was good. read more

Everything has to go right and also be exceptional for a five star from this epicurean. As far as Supper Clubs go there even another me set of standards to go with a dinner spot. They are the real deal. Perfect old fashioneds at the bar with a homemade mix ( usually I prefer the muddled but these were exceptional) included can be the house stuffed blue cheese olives! From there we moved to our table for six and because we all ordered soups and salads we passed on appetizers. The baked French onion was very good and the salads were of the same caliber including the house made peppercorn dressing. There were five stakes ordered that night, one of which was the king cut prime rib and the others were the large fillets. All the beef was exceptional. If there was a spot that could have better it would have been a hotter oven for the crust on the steaks but they were exceptional none-the-less. The other member of our party had a full slab of ribs which she was happy with. We finished with a better than average restaurant coffee and three deserts to pass around. The banana cream pie w/ the graham cracker crust is the house specialty and the other that really stood out was a pumpkin cheese cake. The meal to go along with the exceptional service made for a perfect evening! Cudos to the staff at Diamond Jim's! read more

Supper clubs are so Wisc. Relish tray, peppercorn dressing, French onion soup, prime rib and a good brandy old fashioned. Friendly service and good food. We will be back! read more

See all

Had an excellent meal. Good sized bar. All the classic supper club drinks. Prime rib was perfect. Our server, Jason, was outstanding - times the meal to make sure everything came at a comfortable pace. Nice, old timey feel, with great food. Prices were fair - like that one can spend as much as they want, and could get a very reasonable meal or something more high end. read more

We had a fantastic first time at Diamond Jim's! We were happily surprised by the fantastic friendly service and the amazing food we had. We decided to try them out just this past Friday night December 30. We thought we'd do an early New Year's Eve celebration dinner. The restaurant is very cozy and the atmosphere is comfortable. Our waitress was super friendly and we had a great experience. My boyfriend decided to get the broiled cod dinner and I went for the surf and turf. My steak was cooked perfectly medium rare, and the lobster tail was delicious. My boyfriend enjoyed his broiled cod. The cocktails were delicious. I had a bloody Mary, which was fantastic. I truly was a wonderful experience in the staff was so nice. We will definitely go back! read more

See all

Had the prime rib it was awesome,the atmosphere is comfortable and cozy. My waiter was not on his A game. He took our beverage order came back in less than 5 minutes and couldn't remember what went where ( 2 drinks-2 people). Then our food came out he put my king prime rib in front of my wife and her sauteed shrimp in front of me ( again not right). Two weeks earlier we were at a very nice steak house with 7 people that waiter never made a single mistake. We will definitely go back just a tad bit annoying. Hence the 4 star rating otherwise the food was 5star all the way. read more

After many years of dining at Diamond Jim's, we won't be back. My mom called them for a reservation and during the conversation with the hostess, asked if there was a ramp for entry. She recently began using a walker and can no longer use stairs. She recalled from prior visits that there are only stairs for entry. The hostess responded in a dismissive tone, "we have people who can help older people up the steps" (while my mom did not identify herself, the hostess just assumed she was an older person). The hostess continued, "we were grandfathered and don't have to provide a ramp" (presumably referring to the Americans with Disabilities Act ADA). My mom had her cell phone speaker on and I overheard the entire dialog -- it sounded so bad. The hostess essentially told a long-time customer how unimportant she is to Diamond Jim's. To install a ramp next to some stairs isn't like moving a mountain, it takes some wood, some nails and elbow grease and a kind heart. It's not hard. People with different abilities just want to feel like everyone else -- but they won't at this establishment. read more

Had a great family outing to Diamond Jim's to kick off the holiday season! The place was bustling for holiday cheer! From the specialty drinks (Pear Martini, Jingle Bells Slush, Raspberry martini) to the delicious French onion soup to the unforgettable steaks (bone in ribeye, prime rib and filet). This place never disappoints! We wish we had room for dessert but we couldn't fit another bite in! read more

My cousin from the Dell's was looking for a good "old fashioned" Supper Club, and a good Old Fashioned... We found it Saturday night. Great Prime rib and Ribeye - cooked to perfection. Service was outstanding. Will repeat!!! read more

Food was amazing!! It was opening day for deer hunting so not very busy. Would differently go back

Our first visit was exceptional! We had heard great things from friends about Diamond Jim's Steakhouse and they were right. You definitely want to come hungry! The staff was phenomenal! We had excellent service and our server was very attentive. She was quick with refills to our drinks and was very helpful with recommendations. We started with an order of potato skins because we listened to our friends and came hungry. The potato skins were flavorful and loaded with cheese and bacon. The flavored sour cream added an extra dimension to the skins, too! We both chose a salad to go with our entrees. The salad was crisp and green, fresh and cold - a delicious starter! For dinner, we both had the Filet Mignon. The Petite Filet Mignon (8oz) was more than enough food for me, while my husband opted for the full 12 ounces. The steaks were thick, with a perfect char, and cooked perfectly. They were tender and full of flavor, served with au jus! In addition to your choice of potato and mushrooms or onions, our meals were served with vegetables. I loved the seasoned baked potato, served with sour cream. It was hot and delicious. The onion rings were a great addition to the plate and were perfect. The green beans were just as delicious as the rest of our food! We've heard great things about the Banana Cream Pie, but we were too full to try it. Hopefully, next time we can take some to go. Our first visit will not be our last! Everything was excellent - we even enjoyed the music (a mix of everything) playing in the background. We had an exceptional dinner and thoroughly enjoyed the ambiance of the restaurant. We look forward to bringing our friends! read more

See all

They are not handicapped accessible. I'm pretty sure this is considered a violation against the disability law. Don't understand why they are preventing handicapped people to eat there. I wish I could put negative as review because I don't think this is right that they have been getting away with this for years read more

I wanted to go here. Had my heart set on it. Always looking for a friendly Supper Club to visit. But after calling this place, I am clearly reconsidering. I was given a gift card, it was for Stoneridge Inn Supper Club. Apparently a prior owner. I called and was told they couldn't honor it. They told me they didn't even have a way to check its balance. And I completely understand that. But the person I spoke with was more interested in exerting her authority than being understanding. The power to say NO is evidently intoxicating for her. A savvy manager would at least say 'Gosh, I'm sorry we can't use that gift card, but come on in, stop at the bar... we'll buy you an Old Fashioned and you and your family will enjoy our establishment. But instead.... Unable to think or behave like a place that wants your business, they decide to shut me down on the phone. I will take my family to another Supper Club that is interested in wanting a customer. read more

Diamond Jim's Steakhouse - Garbage... - Steakhouses Near Me - Hales Corners, Wisconsin