Around nine on a Thursday night, the barstools at Cullum’s Attaboy are filling up and Jason Cullum is doing what he does most nights: making drinks, cracking jokes, and remembering what you had last time you came in. That last part matters more than it sounds. This isn’t a bar where you flag someone down. It’s a bar where someone flags you first.
Cullum’s Attaboy sits on St. Mary’s Street in the Beacon Hill area, a stretch of road that has quietly become one of the more interesting corridors for bars and restaurants north of downtown. The building is small — maybe fifteen seats at the bar, a handful of tables — and the whole place feels deliberately proportioned. Not cramped, just considered. The lighting is low without being precious. The shelves behind the bar are stocked with the kind of specific bottles you recognize if you pay attention to spirits.
Jason opened Attaboy in 2018, and if you go on a regular weeknight, there’s a real chance he’s the one handing you your drink. He came up through cocktail bars that took the craft seriously, and it shows without being obnoxious about it. He’ll ask what you’re in the mood for — spirit, flavor direction, how strong — and work from there instead of just pointing you at a menu. The menu exists, and it’s worth reading, but the best thing you can do is describe what you feel like drinking and let him figure out the rest.
The cocktails run in the $12 to $15 range, which is fair for what you’re getting. Everything is made to order, nothing is pre-batched or rushed. If you order a sour, the egg white is actually going to be there. If you order something stirred, it’ll be properly cold. These sound like low bars, but you’ve been to enough bars in this city to know they’re not always cleared.
What keeps people coming back to Attaboy isn’t any single drink — it’s the texture of the place. The regulars talk to each other. Jason introduces people who he suspects will get along. There are nights when the conversation at the bar becomes one long group conversation, and that happens because Cullum runs his room that way. He’s not a performer, not doing a bit. He just runs an honest bar and happens to be good at it.
If you’re going for the first time, a Friday or Saturday will show you the room at full tilt, but a Tuesday or Wednesday shows you something closer to its real character: a few people who clearly live nearby, a few who drove across town, and Jason behind the bar keeping it all loose. Order a whiskey cocktail if you want to see what he does well. Don’t be in a hurry. The bar doesn’t reward that.
Parking on St. Mary’s can be annoying — plan to walk a block or two. The bar is cash-friendly but cards are fine. Hours tend to run from around five in the evening through midnight or so, later on weekends. Check their Instagram for anything unusual, since the place is small enough that a private event can close it off without much notice. Go on a night when you don’t have anywhere to be after.
