Where to Eat Now: Crooners & Cocktails

  • Chefs de cuisine Andrew Rivera-Myers and Jason Daly.

  • A dish of pan-seared monkfish is served over lobster and spinach risotto.

  • Bartender Alanah Meeks works gracefully mixing and pouring drinks from a list of old-school, updated favorites.

  • A Boulevardier, one of the many retro-inspired drinks on a cocktail list that also includes flaming martinis.

Flaming martinis and some truly find food make this updated supper club a hot destination.


The owners and staff at Crooners and Cocktails are so dedicated to this new venture that they all got matching tattoos of the restaurant’s logo. Co-owner and executive chef Christopher Harris rolls up the sleeve of his crisp white dress shirt to show me his. The vertical double C is skewered with two olives on a pick, bringing to mind the kind of classic martini associated with Dean Martin and other crooners of the mid-twentieth century.

It’s this image that is the fully realized theme of Crooners and Cocktails, which opened last May on upper Exchange Street. Harris and co-owner and general manager Rick DaSilva handled all the design work themselves, using inspiration from the supper clubs of that era to create a space that’s seductive and moody.

Harris, DaSilva, and investor Fred Murphy have been friends for more than 15 years, having worked together at restaurants and bars both locally and away. One night last fall, tired of working for others, “we grabbed a bottle of whiskey and wrote up a business plan,” Harris tells me, clearly savoring the memory. “We’re young and hungry. I knew we could find a way to make this work. We’re just local guys who made it happen for ourselves.”

Harris and DaSilva work closely on every aspect of the business, putting in many hours week after week. In the kitchen, you’ll find another duo working together, chefs de cuisine Jason Daly and Andrew Rivera-Myers. Each has his own strengths and specific talents. They are eager for me to know that nearly all of what is served at the restaurant is made in their kitchen, from sausage and pasta right down to the ketchup and mustard. To illustrate the point, they bring out a charcuterie board laden with a variety of their own creations, including house-made ricotta infused with rosemary, creamy chicken liver mousse, citrus fennel sausage, and sweet pickled red onions. Each item complements one of the others and is an impressive start to a meal or an excellent snack to accompany a drink. It’s a more modern—and certainly more delicious—take on the tired relish tray that used to appear on dining tables back in the day.

The menu at Crooners and Cocktails reflects the restaurant’s theme. “It’s not comfort food,” says DaSilva, “but food that you’re comfortable with.” In a move away from the current trend of esoteric ingredients and fussy plating, this is food your parents may have dined on in the 50s, but so much more interesting. There’s filet mignon and lobster Thermidor, both standards of that era, but each one is updated with sides such as decadent confit potatoes or grilled broccoli rabe.

A short but tempting dessert list definitely deserves attention. Like the rest of the menu, these are classics that have stood the test of time, but the chefs have rejuvenated them for contemporary palates. Toasted banana bread pudding is served with crème fraiche ice cream instead of the expected vanilla. Then there is what is essentially a childhood treat: the deconstructed s’more. Sophisticated and sweet, the dish holds toasted bourbon marshmallow cream, rich dark chocolate mousse, and graham cracker crumble. It’s what a s’more wants to be when it grows up.

Crooners and Cocktails serves food until 1 a.m., unusual for a Portland restaurant. At that late hour you’ll often find workers from other Old Port restaurants gathered for a drink and something from the special bistro menu, which includes oysters, deviled eggs, and of course a big burger.

With old standards like Glenn Miller’s “In the Mood” playing on the speakers, delightful food, and a passionate staff, Crooners and Cocktails is a reminder that classics live forever.


Crooners & Cocktails | 90 Exchange St. | 207.536.0469 | croonersandcocktails.com


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