1) When Richie gives Tony the Rocco DeMeo jacket, Richie brags about his own toughness in getting the jacket. Richie is telling the story to Tony while Junior & Bobby are nearby. Richie described Rocco as the toughest guy in Essex County and never came back after dealing with Richie. I don't think he meant it with mean spiritedness, but Junior responded "He later died of Alzheimers."
2) Aaron, Janice's narcopletic boyfriend, sees Jackie Jr. for a second time and asks "have you heard the good news?" Jackie delivers his best line "We met. Thanksgiving." But it was in a sarcastic tone of "you dumb ass I heard this one already."
