If you are looking for a spot that leans into the speakeasy vibe without taking itself too seriously, Wiseguy Lounge on Massachusetts Avenue is worth a visit. It is tucked inside Goodfellas Pizzeria, so you get a cocktail lounge and a pizza place under one roof, which is a convenient combination for a night out. The room is set up with dimmed lights, comfortable seating and a lively music backdrop, the kind of place that works as well for a date as it does for a group of friends.
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The drinks are the real draw here. Wiseguy is known for an extensive bourbon selection and handcrafted cocktails made by bartenders who clearly know their way around a bar. A few standouts have earned a reputation: the Espresso Martini is frequently called one of the best in Indianapolis for its balance, the Smoked Old Fashioned is a sophisticated take on the classic, and the PBJ Shot is an inventive, sweet-and-savory twist. There is also a full line of zero-proof options for anyone skipping alcohol, with names like Rosie Red, Agent Orange, Berry the Evidence, Peach Please, Berries & Cream, Me Espresso and Spill the Tea.
Since it is mid-October, the fall cocktail menu is the one to order from. The seasonal list runs through the autumn and includes World on Fire, Adriana I'll Shoyu, Kiwi Be Friends, The Lumberjack, Harvest Moonlight and The Other Side. Between the bourbon, the cocktails, the beers and the zero-proof drinks, the menu is deep enough that you will not run out of things to try.
And because it is inside Goodfellas, you are never far from a pizza. The parent restaurant is styled like a New York-style pizza counter, and its claim to fame is the gigantic, hand-tossed 22-inch pie, made fresh daily. A 12-inch pizza is $14, a 16-inch is $19 and the 22-inch comes in at $25, with breadsticks at $4 and extra sauces running from $0.95 to $1.89. A 16-inch half-and-half pizza is also $19, and calzones, meatball subs and 60-centimeter breadsticks round out the menu. One detail worth knowing: the kitchen serves food until 3:00 a.m., so it is a reliable late-night option when most other places have closed for the evening.
On the food side, the Buffalo Chicken Cheese Bread is a popular appetizer that pairs well with a drink. The combination of gooey cheese and spicy buffalo chicken makes it an easy share to start the table. Between the cocktails and the pizza, the menu covers both ends of the evening, from an early dinner to a late-night round.
For a bit of context on the place, it holds a 4.6 out of 5-star rating across 251 reviews, with several regulars calling out bartenders Richard, Warren and Andrew by name, along with the doorman. A couple of reviews mention the room can get very hot and another pointed to a lack of service, so it is worth keeping in mind, but the overall consensus leans strongly positive. Wiseguy Lounge sits at 545 Massachusetts Ave, Indianapolis, IN 46204, and you can reach them at +1 317-602-3401.
