Michael Gandolfini as Joey Dwyer, Bobby's son. Finn Robbins (year 1), Mikey Moughan (time 2) and Dion Costelloe (year 3) as Adam, Eileen's son who life with her mother. Jim Parrack as Russell, a movie editor who gets Eileen's boyfriend. Michael Stahl-David as Kenneth, a boyfriend of Paul's and small business companion in his new club. Michael Kostroff as Rizzi, a desk sergeant in Alston and Flanagan's precinct.