Jolly Bob’s

We walked in on a weekday and were seated right away. Warm, chewy, tangy bread arrived immediately while we perused the menu. We settled on 2 empanadas, the black jack shrimp, and chicken well curry. The empanadas were excellent, the salads that came with our entrees were very tasty (though I would ask for no red onion) with interesting dressings, and entrée portions huge and extremely yummy. We didn’t sample any drinks but the menu looked great. Would definitely come back!

Pretty awesome bar! Went here for a few pre-​dinner drinks with a few people, it was right across from where we were going to eat so it was the only thing that was close enough to walk to.
The outside doesn’t look like much, but you walk in and it feels, smells, and looks like you’re somewhere warm, and tropical. The outside looks like a place that would be super small, and crowded place. But it’s actually a pretty good sized place.
We all sat down at the bar, with the tropical music playing in the background. Two of us got the everyday $ 3.00 Coronas, the other two got fruity, tropical drinks, very fitting.
The roommates and I talked about coming back to actually eat, and have more of the yummy drinks very, very soon, especially with it getting colder out.

If the Supreme Court ever approves human + appetizer marriage, I will immediately propose to the chips and guac at Jolly Bob’s because I want to spend the rest of my life with them.
Good drinks, good food. Service a little slow, but it was a busy Friday.

Ok I don’t very often post reviews, but its two weeks after eating there and its still on my mind so I figure I should say something. If I could give a negative star I would… raw food when its supposed to be cooked should be an auto negative!
I should have known after reading rave reviews about the drinks, but very little about the food that I should have stayed away. All I can say is this was the worst meal I have ever had in Madison, and I have had some bad ones.
A party of 3, my husband, his mother and myself. We were seated near the fish tank, in the fairly dark back ½ of the room. As soon as we sat down my husband looked up because something was dripping from the ceiling on his head. He endured a few more drips before moving to the other side of the table.
Our server was a peach, very sweet and good at her job. That was the only good part I can really say. They ordered the bisque and it came out lukewarm, but my husband said it wasn’t bad. Then came the salads: Iceburg chunks, with some jicima, crutons, mandarine oranges and some wilted greens. I orderd the strawberry vinagrette, it was chunky pink glops on the salad and tasted off. I figured it may just be me not likeing their «jerk» seasoning mixed with the strawberries, but my husband who had a different dressing also thought his was odd.
It got worse for the entrees, I had the pecan crusted grouper; DH ordered a bone in seasoned pork; MIL Jerk Pork. MIL complained that it was too peppery, but I can’t completly fault the restruant for that since she did order Jerk. But. hubbys pork was a tough as shoe leather, and had no bone. He couldn’t even cut it with a knife, he ate 2 bites and left it. Now my grouper was the straw that broke the camels back… the pecans were burnt, yet the fish was still RAW in the middle. The only way I can figure this is that it was cooked frozen, how else do you burn the outside and keep the inside raw.
At least the server took my fish off the bill, but we were charged for everything else! The only thing I had for dinner was a few pieces of bread and a few chunks of jicima that didn’t have the pink glop dressing on them, hubby had a bowl of soup and about ½ his salad. MiL had half her jerk and most of her salad and soup… and the bill still came to over $ 70… for inedible food.
I cannot recommend this place to anyone, and will NEVER go back. I thought I should write this review so you can create your own opinion based on my experience there. I hope the waiterss we had can find a better place to work, since she was the only good part of the place.

Worst experience ever! Rude staff, marginal food, and filthy. Definitely will not patronize this place again.
Let me start by saying that Jolly Bob’s used to be a decent place with a nice atmosphere, but it has taken a definite down turn within the past year. I had not been to Jolly Bob’s for awhile, so I recommended to a couple of friends that we stop there on a Friday night to grab something to eat. These are the highlights of our visit:
1. Paid a cover charge to enter the restaurant to eat (what restaurant charges a fee to get in the door to order food? Jolly Bob’s does!)
2. Placed an order for food and was asked to pay (CASH ONLY) before the order was even sent to the kitchen. (Rude guy literally slammed my change on the bar and never asked if I would like anything to drink (water)). Friends looked at me shocked and asked if I knew that guy. (No, no I did not).
3. Friend «A» asks for a menu and the rude guy replies «Your friend has a menu», and walks away.
4. Friend «B» orders a margarita and is told they are out of the particular liquor required to make it. (Huh? A Caribbean restaurant that can’t make a margarita on a Friday night? Ummm, okay.)
5. I ask for a drink menu to suggest drinks to friend «B». Extremely rude lady pushes a drink menu towards us and says, «but it’s in Spanish» and walks away. (First of all, who is she to assume that I am not literate in Spanish? Second, the menu was in English.)
6. I attempt to help friend «B» order her drink and the rude lady asks if we are ordering two drinks and we clarify that we are ONLY ordering ONE drink (for friend B). We are then served TWO drinks and given a really big attitude when I refused the drink (I was the DD). Rude lady promptly snatches my friend’a drink away (without asking) and pushes the second drink in front of her. (Friends look at me confused and ask if we can move to a booth because they were feeling so uncomfortable around the rude lady.)
7. We move to a booth where we promptly stick to the seats (gross).
8. Go to the bathroom to find water and whatever else all over the floors, an odor of urine, and used toilet paper on the floor. (Nasty. And it wasn’t even late and they weren’t even busy).
9. Food comes. Conch Fritters were way over fried (almost burnt) and extremely salty. Steak skewer was «okay». Chips and guacamole were good.
10. Finally, a redeeming effort! An extremely personable, professional, and friendly African American gentleman (I don’t know his name) came over as we were leaving and apologized to us and offered a refund for the Conch Fritters. His actions were the ONLY positive thing about Jolly Bob’s.
11. We went somewhere else and all decided that we would never patronize Jolly Bob’s ever again. I profusely apologized to my friends for having recommended Jolly Bob’s. Friends were so shocked by the incidents at Jolly Bob’s that they kept mentioning how horrible the experience was to other people/​friends throughout the night.
I will never be back to Jolly Bob’s and I will never recommend Jolly Bob’s to anyone. Such a shame, Jolly Bob’s used to be a really neat place with good food and a welcoming atmosphere.

One cuisine I wish was more common in Denver is Caribbean food. So I was particularly excited to try it when I was recently in Madison visiting friends. Jolly Bob’s was quite excellent. I had some tostones for an appetizer, which was a great surprise as I haven’t had tostones since I had a Puerto Rican housemate in college. These weren’t as good as those and the guacamole could’ve used a bit more spice I thought, but they were still a nice trip to fond food memories.
I had some delicious tropical drink thing that was pretty good, though it took quite awhile for it to be served. Service here generally was a bit slow.
For an entrée, I had the jerk chicken. It was a decent version though I also felt the spices could be upped a notch. It came with a salad that I actually thought was better since it had this wonderful curry mango dressing that should be put on practically anything. It also came with some peas and rice. I asked for some dressing for those and it went very well together.
With their expansive patio painted in pastels, I had a brief thought that I was actually in the islands somewhere instead of Madison, Wisconsin. That means they did their job.

This place is great! Excellent patio. Extensive cocktail menu. Delicious food! Worth checking out for sure.

Worst service I have ever recived in my life. Ordered food for my toddler to come out first and it came out last. Waitress was awefull and tried making excuses why a table that was seated and ordered after us had there food before us.

Soooooo delish! Love the authentic look, love the super friendly staff, love love love,

Feels like management doesn’t care about your customer experience. From poor site maintenance (see picture of bug covered paint chipped entryway) to habitual under staffing behind the bar… it seems as though someone has given up. I appreciate that the delicious cocktails take time, but staff for it. Several times, after waiting 30 minutes to get a drink, I hear, «sorry, we only have one bartender.» STAFF MORE BARTENDERS! I don’t know maybe two would be better than one. Management controls staffing, fix it.

This place is by far one of the must go-​to places in Madison. The food is so unique and delicious. However, I have noticed if you sit in the back patio area, you will be sitting at a slant and covered with bugs and twigs from the surrounding trees. When I sat at my table I was taken to recently, there was dirt, bugs, twigs, etc., all over my table’s plates. Is it still worth going? Absolutely. Just avoid the back patio area.
Also: The napkins ALWAYS smell like mildew; pretty unpleaseant.

Such great food and atmosphere. Jolly Bob’s is one of my favorite Madison restaurants. The drink menu is fun and Caribbean themed. I have tried most things on the menu and each dish is excellent. The outside patio is wonderful in the summer, but indoors is also nice for a mini-​vacation in the winter. Definitely a great place to take out of town visitors.
The front of the house can be a little unorganized, and last I checked, the restaurant does not accept credit cards so make sure you come with cash/​check.

If I could give this establishment a ‘0’ out of 5 stars I would. This restaurant has the taste of racial profiling sprinkled throughout – from the bouncer all the way to the owner. Since the recent incident that resulted in the dismantling of Reggae nights, they have creatively restricted black people of all socio-​economic classes, from entering their restaurant.
This past Saturday, I arrived before 10pm, at which they start charging a cover to get in – the bouncer insisted that I pay the $ 8 cover charge to come inside. I initially tried to bargain, but then finally stated I just wanted to tell my friends that I would be leaving. After coming back outside – I saw a bouncer give a white female a hug and let her go in without paying.
I wouldn’t go back to this restaurant again if it were the last place in Madison that had food. It is disgusting and further optimizes the epitome of the racists attitude that is evoked throughout this city.

Stopped by Jolly Bob’s for the first time on a whim one night, as other dinner plans fell through and we were wandering Willy Street in search of grub. What a happy accident!
I should mention this night was particularly cold. Jolly Bob’s was a wonderful little «staycation» with tropical drinks, spicy food, and a cozy atmosphere.
I had a Love Lotion, per the bartender’s suggestion, and later a caipirinha (a go-​to drink of mine) with dinner both were strong enough and tasty!
For dinner, I went the snacking/​tapas route, ordering each of the beef empanadas (one curried, the other not), a jerk pork pincho with banana ketchup, and papas bravas (potatoes in a spicy tomato sauce). I looooved the empanadas, though one was a little short on filling. The pork was a little bit dry and not a great temperature. And the papas were pretty good, though the sauce was chunkier than expected, more like pico de gallo and less like the smooth sauce I’ve become accustomed to.
Our waitress was really informative, though sometimes a bit abrupt, cutting people off when speaking.
I’d happily go back for drinks and empanadas any time!

I consider myself a Jamaican food enthusiast and I was truly not impressed with the quality of the food. It’s was simply OK, along with the service and the drinks. The atmosphere is nice though especially for a date night or one on one.

Painkiller. Go. Drink it. It will fix what ails you.
Great cocktail menu. I have yet to eat here, but the drinks are great. Patio outside is neat as well. Perfect place to go to when you want to forget you’re in central Wisconsin for a few hours.

I love Jolly Bob’s!!! They have the most delicious cocktails which I love because I was a bartender for years and love creativity in beverages. Last time I was there I actually ate dinner for the first time and had a blackened shrimp/​rice dish which was incredible! Their best kept secret is the outdoor patio out back. It seems almost tropical in the warmer weather with the amazing array of trees.
Keep in mind it’s cash only!!! :)
Thanks for all the good times!!!

We only came here for drinks and had the mango daiquiri (I could drink that baby ALL night) and the purple meanie. Don’t remember what was in the purple meanie, but my boyfriend enjoyed it. Will try to come back for the food some time but the drinks are enough for us to come back!

Jolly Bob’s has a fantastic cocktail menu from which my wife ordered. It looked delicious! I was in the mood for one of the local favorites on tap, but it came out rather flat. Next visit I think I’ll stick to the cocktails.
All the entrees come with a house salad including an array of four or five dressing to choose from. I chose the mango curry dressing, which I did not regret one bit. The mix of sweet and spicy was an excellent foreshadowing of meal to come. The salad was served as a pyramid of lettuce surrounded by some appetizing mix-​ins.
For the entrée I ordered the beef tenderloin. I didn’t think the cut of meat was great for price but overall I was pleased with the dish. It was served with an amazing salsa, a fried egg, pickled red onion and fresh avocado, all of which complimented the beef well. On the side were some of the best sweet potato fries I’ve ever tasted.
We ate inside — it was a touch dark and cold for an outdoor meal. Inside was nice but there was no danger of an overwhelming sense of being lost in the Caribbean. The giant fish tank in the middle of the restaurant housed only three small fish.

This is hands down the best restaurant in Madison for the unhyped, properly priced, on this side of pretentious ;)
I have had a long love with Jolly Bob’s and I always will. The décor and size make it a place that seems packed all the time, but don’t let that deter you. Drink a purple meanie and chill until your table is ready. I love the curry cream mussels, the black jack and the curry chicken or pork.
This place is a staple in Madison and a place everyone should eat or drink at one time. Oh and the aforementioned Purple Meanie — I’ve been able to drink 4 of them. While I’m proud, I would not suggest it to anyone. Car and driver required :)