Based on Yelp reviews we came on a Sunday night dinner date as first time customers. The restaurant did not disappoint. Parking is available across the street and we got the last spot. The place looks like a diner from the 1940s and probably hasn't been renovated or updated significantly since it opened in 1937. It's well-worn but the dining room was clean and comfortable. Since they are famous for their pizza, we ordered a cheese pizza with mushrooms which proved to be tasty. We also got the chicken and eggplant parmesan which was good but not particularly special; above average diner food. Service was excellent from 2 staff that probably have worked at the place for decades. Portions are generous and prices competitive. We'll definitely return! read more

This is a great place. It is one of the few places left that have character. It also looks like its the kind of place that is hopping every night of the week, and deservedly so. The interior is from the 1950s. Small, cramped booths, servers that look like they have been there forever, and a great casual family atmosphere, energy. I had a salad with creamy Italian ( delicious), a great big piece of chicken parm (delicious!) that came with a side of spaghetti. Oh yeah. They also serve you with your meal, Scali bread and butter. The food was served hot! I loved it! It seems like most places serve you warm food these days. The food was all delicious, friendly service and a really nice time. I tried to get a few slices to go, but they only serve their famous pizza as whole pies. The pizza is the star of the show here I hear, but I would say everything was the star. Great food, reasonable prices and a great atmosphere! I'll definitely have to go back there for their pizza. Beware if you are a little bit uh, big or Alan Thicke as the booths are very tight, a bit small and a bit cramped for my liking. It may be because I'm a little bit big( 6'2" 240 lbs.). I get it. Places generally weren't made to accommodate people my size. If you have never been here...why not?! Total Class place. read more

Pleasant Cafe's taste and price can't be beat. They don't have delivery, so I do pick up but it's totally worth it. Haven't eaten inside before, but there's a solid number of people inside usually and the servers seem nice when I pick up my pizza. The decor/interior seems pretty retro. I love their pizza and don't think you can beat it anywhere else in Boston! read more

The Pleasant Cafe - Cheese Pizza - Pizza Near Me - Roslindale, Massachusetts

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Old school in the best way. Affordable and consistently delicious food. The Sherry chicken is exceptional and the the pizza is the best in the area and if you dine in, try the specials, they are always very good. read more

Spot on Monday turkey dinner specials. The cheese pizza always consistently good thin crust. Nothing fancy but keeps prices down!!

We got takeout from here for a dinner with friends. Two pizzas, one with mushroom and peppers and the other with peppers and onions. We ordered on the phone and it took about 35 mins for the pizzas to be ready. They were piping hot when we got them, felt fresh out of the oven. The crust was thin and crisp. The ratio of crust to cheese was perfect. There was a good balance of veggies on top. It was delicious! My only tips for the next person to order are- 1. Their phone may appear busy when you call. Don't give up. 2. They only have a medium size pizza (I wish they had more sizes!) 3. They don't have a "veggie supreme" pizza (Pleasant Cafe, if you're reading this... Hint hint) read more

This place is AMAZING! You absolutely need to visit this iconic Boston eatery! Not only is the food fantastic - and affordable- the staff is outstanding and kind. The pizza is the BEST- not just in MA, but in the country. We've had pizza in nearly every state and none is as good as it is here. Both my father and my husbands father grew up coming here in the 50's and 60's. Love that it's still a time capsule. Visiting from NC and just had a wonderful visit on 1/8 with our mothers. Our waitress was top notch and so patient with us. You need to visit! Update: I just realized I already reviewed the pleasant cafe 7 + years ago (also 5 stars) and mentioned my Dad, who was then still earthside. The man I mentioned as my boyfriend back then is now my husband mentioned in this review. Spilling a few tears now as he passed away in 2019. Like the pleasant cafe, my Dad really was the best read more

The Pleasant Cafe - Pizza Near Me - Roslindale, Massachusetts

Being born and raised in Rozzie (and now turning into an old dude) I've been a diehard fan of this milestone for decades. I don't need Dave Portnoy's opinion -- the Pleasant has been my go-to favorite pizza place for, well, a really long time. I rarely eat in the joint anymore, I get my pizza to go, but I love everything about the place... the pizza, obvi; the vintage '40s/'50s dive deco; and the tough as nails waitresses, too. Always recommended to everyone I know, local to the area, and not. Consistently delicious. FIVE STARS. read more

Service was good , food was meh . Usual salad w ice burg onion tomato it was fine . Nachos had mozzarella cheese WTF ! Canned chili ,and vegetables,chips were those low quality rounds , also not fresh and crunchy . I ordered baked stuff shrimp , four large cooked well but the stuffing was flavorless bready mush . Wife and daughter had prime rib which was excellent. Baked potatoes were delicious, broccoli was steamed soft with liquid cheese . I think if I had ordered a steak and baked potato I would've been happy. Pizza look great , and the place was really filling up at six on a Saturday read more

I hadn't had Pleasant Cafe pizza in over 20 years until recently. It did not disappoint. It was so delicious.

Grew up on pleasant pizza was always awesome Last 2 times it was like eat a box of salt not going back unless they go back to the original recipe read more

The food was great and the service was very friendly. We did takeout, but if I had the time, I would have eaten there. Seemed like a cozy old-timey diner. One drawback, ask for silverware! We didn't get any. read more

This place has been around forever for a reason it's really relaxing they have a full bar and the service is very welcoming. This is my first time and I only had the Pizza but I shall return and try the prime Rib and some parm chicken or eggplant maybe the stuffed shells with meatballs. As for my pizza I had a custom made pie and it was delicious I like this pizza because the sausage had plenty of fennel and the sauce was on the sweet side and the cheese was really good and didn't turn chewy when it cooled off. Come see them if you haven't already. Btw they have a ginormous parking lot right across from the restaurant. read more

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My hubby and I were at my grandson's football game at Curry College. As it was a night game, it wasn't until 9:30 that we said our good-byes. We wanted dinner somewhere and found a GEM! The Pleasant Cafe with it's wonderful owner John and fantastic crew of waitresses, but especially Leigh, filled the bill so much more than we anticipated. We placed our orders of Prime Rib ($23) and Chicken parm with a side of cheese raviolis. OMG! It was amazing. Staff was so friendly, professional, and KIND but the food....sooooo delicious!!! Thank you John and Leigh for a fantastic culinary experience. We WILL be back :-) P.S. they beat the famous Pepe's of New Haven for BEST New England PIZZA! That will be our next meal :-) read more

The Pleasant Cafe - John and I - Pizza Near Me - Roslindale, Massachusetts

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I am surprised that I've lived down the street for over a decade and have never been here. Have always heard good things. Upon stepping in, I felt like I stepped back in time. Honestly, I liked it. There was a narrow room with booth style seating. There was also another room but I didn't look in it. I came here with my family (5 people) and were seated immediately (weeknight at 520pm). They were understaffed but the waitress was very nice and did her best. Service was good. Food was good. Prices were fine as well. The cheese pizza was delish! Mozzarella sticks were good. Crunchy and the cheese pulled as it should. Buffalo chicken was a tad overfried. I asked for buffalo sauce since there was no spice to them. My dad liked his fisherman's platter. My husband thought his chicken broccoli ziti was just okay. He thought it needed more sauce. The pasta was al dente and chicken was fine. My mom loved her broiled haddock. Overall, not bad especially since the prices are pretty good. I would definitely come back and try some other items. The menu is HUGE. Not many healthy choices other than salad. read more

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best pizza on earth no idea how they always make it so perfect, but they do crust is legitimately A+, and the sauce/cheese combo rocks order it crispy with extra cheese and you will not regret it also order a Greek salad with it and you will be very popular when you arrive home read more

I have been coming here for over 40 years and I love this place! Pizza is so darn good and you can't find anything like it anywhere. So perfectly balanced with flavors and texture! Also this place has great cocktails ! A whole menu of drinks on the back... no newfangled drinks but classic like a pink lady to a white Harvey wallbanger . Come and try The Pleasant, you won't regret it! PS the waitress have been there along time and they are Old School!!! read more

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Place has been there for years. It's true old "Rozzi". I love their pizza, but all their Italian food is excellent. Again it's old Roslindale. Not the most updated place, but it's special to many old Roslindale residents. Most of us moved out except the true die hards, but we always go back to are old stomping ground "The Pleasant ". It's just special. Brings back memories of the way Boston was before the yuppie/woke invasion that drove us out. We love this place and many of us would be devastated without it. You wanna experience Boston go to the Pleasant. Many past Mayors of Boston have ate there. Such as Mayor White, Flynn, Menino. Not sure about Walsh or Wu. Probably afraid to step foot in there. read more

We stopped here Black Friday and had a very pleasant dinner. We each had a tasty cup of chowda served hot with a generous amount of clams. My companion had the 3 fish casserole, which came sizzling hot in a casserole with crispy buttery bread crumbs on top, and enjoyed it very much. I had broiled haddock, which was hot, fresh, and flavorful. We split a Boston Cream Pie for dessert which was very yummy: the cake was fresh and light, the chocolate frosting was very good, and there was ample creme anglaise filling. We enjoyed the cake with an Irish Coffee that was hot and had whipped cream on top drizzled with creme de menthe. I want to try their pizza next time. Our waitress was very efficient and served all our food and coffee hot. She came around and checked on us at just the right times. The ambiance was charming old timey with wood paneling and cozy booths. The wooden bar looked antique. Many patrons were regulars and knew one another and visited each other's tables for a chat. It was a convivial and pleasant atmosphere. read more

The Pleasant Cafe - cars parked in front of the restaurant - Pizza Near Me - Roslindale, Massachusetts

I have been coming here for close to 50 years ~ since teenage years. Now the wait for a pizza is 90 minutes and the service is slow.Disappointed that I won't be back! read more

The pizza is delish and is served after 4pm so get it while it's hot! If you are eating in the establishment it is like stepping through time I love it! The staff are a bunch of familiar faces that have been there for years! Welcoming atmosphere not the fanciest interior but super clean and I love the retro appearance. read more

The service was nice. The spaghetti with meat sauce was But the pizza was great. The bread was fresh and yummy but the butter was very cold. The decor was vintage but lovely, clean and absolutely enjoyable. Overall, this was a nice lunch in an authentic place that I would definitely recommend. read more

The Pleasant Cafe - Spaghetti Or Ziti With Meat Sauce - Pizza Near Me - Roslindale, Massachusetts

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The absolute best! Pizza is the best in the world and the veal parm and ziti dinner is . Simply the greatest pizza establishment of all time! read more

This is one of those times where having a 1/2 star option would be nice. As this is more like a 3.5 star review. First, while the people were friendly, there isn't really an area for pickup noted, so it was a little confusing going in and not really knowing where to go. The pizza was good, I don't think it was worth the hype it gets but definitely deserves some props. To me, it was more NY style than bar style that it gets characterized as. Good sauce and cheese, and that powdery texture to the crust and undercarriage, which is why I lean more towards NY style. One size for pizza, and prices are OK. Parking across the street. Wouldn't be worth the 1 hour trip for me to go again , but those in the area should be going. read more

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Pleasant Cafe has the best pizza in town. All the food there is awesome. It's a great place to go with friends or family!!! Service is always great and fast. read more

The Pleasant Cafe - Pleasant Cafe - Pizza Near Me - Roslindale, Massachusetts

Amazing Service. I got some pizza over the weekend. Great flavor and value. I highly recommend this restaurant. Sometimes It can be a little loud but its worthy. I really enjoyed everything about this place. read more

The Pleasant Cafe - Pizza Near Me - Roslindale, Massachusetts

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We love the Pleasant Cafe and come every time we in this western area of Boston. It is consistently good. The waitresses are so friendly. The price are reasonable and the cheese pizza is delicious. I like the Eggplant Parmesan, my husband likes the scallop. read more

Tried the pizza at The Pleasant Cafe in Roslindale last night. In 2018, NBC 10 Boston crowned them as the best pizza in Boston. Quality cheese and tasty sauce, but they lost me with the crust which was more dense and crunchy than crisp and chewy. The judges must have walked in with the munchies. read more

The Pleasant Cafe - Pizza Near Me - Roslindale, Massachusetts

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2 stars and that is ONLY for the pizza and friendly staff. The rest of the food was just horrible. Meatballs as flavorless and HARD as concrete. Frozen cheese ravioli. Antipasti salad with tuna and one and a half slices of salami ?? How generous. And flavorless garlic bread that I've already forgotten about. Probably won't return. read more

Their pizzas are very good. The service you get is top notch and the place is very elegant

Saturday night and the gang wanted pizza. Someone mentioned that this place has been around a long time and it must be good to last that long. Look online at the menu, only 1 size of pizzas. We called and were put "on hold" (the phone was put down and we could hear all kinds of conversations going on) after a minute they picked up on the phone and I ordered a pizza half cheese and half meatball. It would be read in 20 minutes. Thankfully I saw that their website said there was plenty of parking across the street. Arrived 20 minutes later at the restaurant, went into the wrong door (2 or 3 doors to the place) walked the dining room, a bar like area and found a little nook where take out orders where handled with a huge crowd waiting around for something. I told the woman working the phone, I wanted to pick up my order, she picked up a boxed pizza on a shelf asked if I was John, Yep it's mine. Paid and left. The pizza was cold, (I get the feeling it was done early) it could have used more sauce but the kids were happy and that was the big thing. I'm game to try this place again, maybe something different on the menu, maybe even inside the restaurant itself. read more

Got a couple of pizzas recently. Omg the very best ever. One size only, a large! Pizza was sublime and so very delicious. Love the old school vibe there. Wished we stayed as the daily specials were amazing!!! read more

Served warmed not hot. Salad served with main meal. Beer not that cold bottle. I saw two drinks returned due to floating particles in them.

Amazing hole in the wall that's been around for like 80 years. Must try the veal parmesan! It's insanely good.

Ordered 3 pizzas tonight for the first time feel The pleasant cafe. All 3 pizzas were delicious and the service and staff were so friendly. Could not recommend enough if your in the roslindale area!! Love the old school vibe in the building, shows why they have been around for so long! We can't wait to go back and try other items on the menu! read more

I have to say that their pizza is the best I have found on the South Shore! A beautiful thin crust with awesome fresh toppings and perfectly cooked, and the price is the best around. Everything I have had has been super, but my favorite is their pizza's! read more

How would you feel if you ordered a pizza and the plate that came with it had a complete slice stuck to the bottom?

Pleasant environment, but Shrimp Scampi was virtually TASTELESS & lacked any seasonings. A complete waste of money.

Nothing better than an "Old School Neighborhood Place" . I used to come here for pizza with my grandmother as a child and it's still the same great place. I have been picking up tons of pizza and pasta here since the quarantine and it is all delicious. The restaurant has a huge parking lot across the street that is free, which is unheard of in Boston. Before I go don't forget to tip out the server's for your take out orders they work just as hard proviing service now enjoy your pizza! read more

The Pleasant Cafe - The Works with garlic no anchovies! - Pizza Near Me - Roslindale, Massachusetts

Pleasant pizza always hits the spot for me. In fact, I don't think I've ever even gotten anything else here- just the pizza. (Keep meaning to try the traditional turkey dinner- one day!) But let's set expectations here: this is an old school no-frills Boston joint, with all that entails- it's not going to blow you away, there's no fancy toppings or interesting flavor combos, and there's no amazing service to rave about. What you get here is eat-in or take-out standard Italian thin pizza with basic topping options (some of which are most certainly pre-packaged/frozen- looking at you, weirdly uniformly diced grilled chicken and frozen soggy broccoli). But the sauce is flavorful, the cheese is right, the crust is thin and unobtrusive, the toppings aren't totally skimped on, the pizza is consistent, and the joint is a long-standing neighborhood establishment who probably haven't changed a thing in decades and rides high on nostalgia and comfort from people who grew up around here. My go-to is the Hawaiian- the ham is thinly sliced and gets a touch scorched on the ends (also a fan of the linguica), and the plain cheese is also a classic. Be warned, they do have a shit POS/ordering system- you have to call to order (no online), and it can get confusing coming in to pick up (a bit chaotic). Can you find better pizza/restaurants around here? Sure, but Pleasant remains a go-to for those of us in the know/in the area, and beloved by many generations of Bostonians. read more