Dooly’s isn’t one of those dingy, smoky pool halls your mother warned you about. Barrington Street manager Shawn Field is proud of his clean floors and 25 well-lit tables. And you don’t need to master the masse, a 15-ball combination or any other trick shots to have fun at Dooly’s. “We get a lot of boyfriend/girlfriend couples just coming for a good time,” he says. Dooly’s has been racking up wins in this category for years now; maybe that’s why both runner-ups have recently been scratched. 1567 Barrington, 429-2627
1st runner-up: Planet Pool Bar and Diner (no longer open)
2nd runner-up: Breakers (no longer open)