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Exterior of an old-school restaurant with blue, pink, and red signage, including neon accents, that reads Pleasant Cafe.
Good food, good drink, good facade
Terrence B. Doyle/Eater

Pleasant Cafe Is a Reminder That a City’s Dining Scene Is More Than the Sum of Its Shiniest New Parts

Eight decades on and still going strong

Boston’s dining and drinking scene is rich with independent restaurants and bars that have been catering to their neighborhoods for decades. Unfortunately, it’s often the new and shiny venues that get the most attention, and as out-of-town chains and wealthy Boston-based restaurant groups drive up rents and cannibalize operations of lesser means, it’s become more difficult for these independent operations to succeed — or even survive. In a sense, then, Pleasant Cafe in Roslindale (4515 Washington St.) has defied the odds.

Opened in 1937 by the four Iantosca brothers, Pleasant Cafe has been owned and operated by the Morgan and Lynch families since they purchased the bar and restaurant from the original owners in 1979.

“My father, Jack Morgan, and his friend, Jack Lynch, bought the restaurant,” said John Morgan, one of the restaurant’s current owners. “The two families have owned it ever since.”

Pleasant Cafe’s menu is massive (try the chicken parm), but it’s perhaps best known for its pizza, which was recently voted the best in Boston in an NBC 10 Boston viewers poll, edging out well-known classics Santarpio’s and Pizzeria Regina. While Santarpio’s and Regina are making pizza much like you’d find in Brooklyn, Pleasant Cafe’s take is closer to New England bar-style pizza. The crust is thin, and the cheese — there’s a lot of cheese — is blistered and slightly burnt (this is a very good thing.)

Overhead view of a thin-crust pizza topped with green peppers on a wooden table. One slice of the pizza has been removed.
A green pepper and onion pie from Pleasant Cafe

The interior has remained largely untouched since the restaurant’s opening more than eight decades ago.

“The only major change is that the current back room used to be the kitchen, and the pizza room was in the cellar,” said Morgan. “When I worked here as a kid, bussing tables, the pizza used to come up to the dining room on hand-pulled dumbwaiter.”

pleasant cafe back room
The back room, or, the old kitchen

A row of gorgeous aluminum lowboys form the backdrop of the bar. Morgan said that they can be a pain to deal with because they’re so old — he’s constantly having to pay HVAC workers to come fix the compressors, and he’s had to replace more handles than he cares to recall — but he’ll never replace them if he doesn’t have to.

“The HVAC guys always say, ‘Maintain these things because they don’t build ‘em like this anymore,’” said Morgan. “They’re probably not the most efficient things in the world, but they’re solid aluminum, so they hold the cold in very well.”

(Indeed, the beer from the lowboys is in fact very cold.)

bar pleasant cafe
The bar at Pleasant Cafe, with the lowboys to the right

Morgan said that George Parelli — who was friends with the Iantosca brothers and who worked at Pleasant Cafe for more than 70 years, many as a bartender — told him that the mahogany bar dates back to the early 1900s and that it used to belong to a bar in downtown Boston.

Wood panels cover the walls inside Pleasant Cafe, washed monthly with Murphy’s Oil Soap — “My mother is a cleaning freak!” Morgan said — and lined with plaques from local Little League teams, like the Parkway Yankees. Pleasant Cafe is a pillar of its neighborhood, and that’s what Morgan likes best.

“Seeing the different generations come in is a real pleasure,” said Morgan. “Grandparents come in and say, ‘We were engaged here. We brought our kids here, and now they bring their kids in here after Little League games.’ The people you get to meet over the years, it’s just incredible.”

pleasant cafe
A very good sign

Pleasant Cafe has its own generational thing going on, too. Morgan’s mother, Joan — who’s in her late 70s — still manages the day-to-day operations like payroll and ordering. Morgan manages the front of the house, and his wife, Joanie, manages the restaurant’s marketing and online presence. Morgan said that he has employees — servers, bartenders, pizza makers, cooks — who’ve been with him for more than 20 years. Everything at Pleasant Cafe is familiar, which is exactly what makes Pleasant Cafe special.

Head to Roslindale, eat some pizza, drink a very cold Bud Light, and support a locally owned, independent restaurant. Shiny and new is fine, but old and broken-in wins every day.

Pleasant Cafe

4515 Washington Street, , MA 02131 (617) 323-2111 Visit Website