The Sopranos: 10 Funniest Paulie Moments
7. Meeting Meadow's Boyfriend (Unidentified Black Males. Season 5, Episode 9)
Getting on the right side of the boss is a good thing in any profession, but in the mafia it can sometimes be the difference between life and death. Paulie is aware of this and for the majority of the series he not only one of Tony's biggest earners, but also one of the boss' most loyal soldiers.
In essence, Paulie is an expert in "sucking up to the boss" and with such loyalty, words of disapproval or distaste relating to Tony are typically behind the boss' back.
In season 5, Tony helps Meadow's boyfriend Finn land a temporary job at the mob run construction site. Unaware of Finn's relationship with the boss' daughter, Paulie does not hesitate in ordering and intimidating Finn into cleaning his tires.
The lounging mobsters swiftly inform Paulie of Finn's identity and Paulie's sudden face turn tells you all that you need to know! Paulie quickly looks to atone for his misjudgment by giving Finn some money, before then requesting that the increasingly confused boyfriend tells Meadow about his 'good deed'.