This Boston icon is a portal to an older time — with pizza as great as ever

It seems like with each passing year, more and more of Boston’s old-school restaurants and bars say goodbye.

There are a number of reasons for this. In some cases, it’s simply because the owners decide to retire; in other cases it’s due to redevelopment, rent increases or dwindling business. Whatever the reason, the bottom line is that the comfortable old neighborhood dining and drinking spots seem to be endangered.

That’s why it’s so refreshing to see a place like Roslindale’s Pleasant Cafe not just still open, but also seemingly thriving, especially on the back end (knock wood) of the pandemic which wreaked havoc on the local restaurant scene over the past three years.

There are very few places within Boston city limits that deserve the “iconic” label (J.J. Foley's in the South End, Santarpio’s in East Boston and Caffe Vittoria and Pizzeria Regina in the North End are a few others) and this longtime local spot certainly does warrant that badge of honor.

While much of the dining scene in Roslindale centers around Roslindale Village (or as some call it, Rozzie Square), a few other restaurants and bars reside on the outskirts of the neighborhood, including the Pleasant Cafe, which sits high above the village — with downtown Boston in the distance — near the West Roxbury line. The area feels a bit more suburban than much of the rest of Boston, especially as you continue through West Roxbury toward Dedham.

Because this section of the city is a bit less densely populated, it isn’t uncommon for businesses here to have their own parking lot, and the Pleasant Cafe’s rather large lot is just across the street. Crossing the street to the restaurant is a classic old Boston experience unto itself, with the restaurant’s vintage neon sign and frosted glass welcoming diners like it has been doing since the 1930s.

The interior of the Pleasant Cafe is every bit as charming as its exterior, with a setup that used to be much more common many years ago. The place actually consists of two separate spaces — each with its own entrance — with a long and narrow wood-paneled dining room to the left that includes two rows of booths and a similarly long and narrow bar area to the right that includes the type of wooden bar top that seems right out of a black and white movie. The bar section has a partition that subdivides it into two spaces, one with more seating.

The dining room and the bar area are connected by a couple of doorways, and the dining section is arguably the busier space (depending on what time you go) where you’ll typically see parents and their children, groups of friends and couples.

And the service at the Pleasant Cafe is an experience in itself. The people who work here are typically friendly, funny and sassy, which brings to mind such places as Newbridge Cafe in Chelsea and Greg’s in Watertown, two other can’t-miss neighborhood joints in the area.

The Pleasant Cafe, like so many neighborhood spots around Boston, has a menu that focuses at least in part on Italian-American fare. Here you’ll find such hearty options as stuffed mushrooms, toasted ravioli, lasagna and meatballs, prime rib (which is typically a traditional Saturday night dish at places like these), baked stuffed shrimp, chicken parmigiana, ziti with Italian sausage, a hamburg steak dinner, roast loin of pork and pizza.

Pleasant Cafe: Great pizza in a classic Boston restaurant

The pizza here, by the way, is often included on “best of” lists in Boston, but beyond that, the pies, which lean a bit toward foldable thin-crust New York-style with just a hint of South Shore bar pizza mixed in, easily go up against some of the best pizza in all of New England, coming close to the heights of New Haven pizza — which is saying a lot.

Some may look down on the drinks list at the Pleasant Cafe because, well, it includes simple cocktails that go back many years, not the type that you might see on “retro” cocktail lists at some of the newer and trendier places. When, for instance, is the last time you saw a Tootsie Roll offered? A Galliano Stinger? A Brave Bull? A California Root Beer?

You will find these and approximately 75 other cocktails from the wayback machine on the menu, and you may find yourself frantically Googling some of the drinks on the list to find out exactly what they are before the server arrives. The Pleasant Cafe also offers a handful of beers and wines along with soft drinks, but the cocktail list on the back of the menu is, for many, one of the highlights of any meal here.

The Pleasant Cafe is a little like an old, comfortable shoe — it feels instantly familiar and no matter how hard others may try, they’ll never truly be able to match it. When Doyle’s Cafe down the street in Jamaica Plain closed in 2019, the city of Boston was hit with an immeasurable loss, but this landmark Rozzie spot took up the slack for many with its similar (though lower key) vibe, and while Doyle’s may eventually return, no one really knows if it’ll have the same feel as it did before.

In the meantime, The Pleasant Cafe continues puttering along, welcoming both regulars and newcomers to its warm and homey digs.

Pleasant Cafe, 4515 Washington Street, Roslindale, MA, 02131. pleasantcafe.com