The characters in The Sopranos talk a lot. After all, there is always a burning issue every minute of the day in the fictional New Jersey and New York underworlds seen in the critically acclaimed HBO show. And after the business has been handled, there tends to be enough room for gossip, jokes, and bickering. Dialogue is, therefore, one of the show’s strongest pillars — stronger than the violence and only second to the plot.
Over the course of the series, both the major and minor characters associated with the DiMeo and Lupertazzi crime families make plenty of memorable remarks, but a few bits of dialogue stand out more because they are either clever or funnier. Others are mere threats or misquotes but the manner in which they are delivered makes them more iconic.
15 “You are only as good as your last envelope.” – Silvio in “Eloise”
In organized crime, a mobster’s earning power is what determines their value. Silvio reminds Paulie of this fact after he starts worrying about his position in Tony Soprano’s criminal outfit. Ordinarily, there is a clear pipeline in the flow of money. Street soldiers are required to submit a percentage of their income to Capos then the Capos give a portion to the boss.
The DiMeo crime family consigliere explains to Paulie that the only reason Tony might be snubbing him is that he is submitting a thinner envelope. He assures him that doesn’t need to suck up to anyone. All he has to do is earn more. Silvio’s theory is accurate and is best demonstrated through Tony and Ralph’s relationship. Despite the latter’s recklessness and cruelty, Tony tolerates him for a long time because he brings in more money than anyone else.
14 “The guy was an interior decorator. He killed 16 Czechoslovakians.” – Paulie in “Pine Barrens”
In just about every episode, Paulie Walnuts does things to remind fans why he is one of the coolest Sopranos characters, but none of his actions can beat him misquoting Tony while he and Christopher are chasing after the Russian mobster, Valery, in the snowy New Jersey Pine Barrens. On the phone, Tony tells Paulie to be careful because Valery once killed 16 Chechen rebels during his days Russian Interior Ministry operative, but he relays a distorted message to Chritopher.
Only a comical character like Paulie is capable of hearing “Interior Decorator” instead of “Interior Ministry” and the remark is intriguing because he doesn’t even pause to figure out whether whatever he is saying makes sense or not. It would be odd for an interior decorator to kill all those Czechoslovakians for no reason. On top of that, Christopher’s reaction makes the quote cooler because he wonders how the hell Valery is an interior decorator, yet his house is so disorganized.
13 “He never had the makings of a varsity athlete.” – Junior in “Where’s Johnny”
There are only a few things Junior enjoys more than stepping on Tony’s toes and during one Sunday dinner, he does so again, telling everyone that his nephew never had what it took to be an athlete. Junior knows that the remark makes Tony uncomfortable because he had dreams of playing football, but he couldn’t pursue the career because of discipline and fitness issues.
Interestingly, this isn’t the first time the senior DiMeo crime family member says the words. In the prequel movie, The Many Saints of Newark, a younger Junior is shown making the same remark, infuriating Tony in the process. And it’s easy to see why Tony gets angry because the words remind him that there is something, he isn’t good at and that he would have had a more honorable career if he wasn’t so unruly and undisciplined.
12 “Let me tell you a couple of three things.” – Phil Leotardo in “The Blue Comet”
Lupertazzi crime family boss, Phil Leotardo’s hatred for the DiMeo crime family is evident from the moment he is introduced, and by the tail end of the series, he becomes so fed up that he issues orders for the entire top brass of the New Jersey outfit to be whacked. There is some opposition to the order, with some of his fellow mobsters feeling it’s not such a good idea. Incensed, Phil offers to list down their enemies’ three major sins.
The way the villain messes with grammar makes the quote more enjoyable. And he doesn’t just say three things. He goes on a long rant, proving just how much, he hates Tony and his crew. Here, actor Frank Vincent channels the kinds of mannerisms he did while playing the Gambino crime family member, Billy Batts, in one of the greatest gangster movies, Goodfellas. Both Billy and Phil are angry and aggressive, but such attributes eventually get them killed.
11 “Dad, are you in the mafia?” – Meadow in “College”
As Tony and his daughter Meadow are driving to Maine to check out three colleges that she is interested in joining, she stares at him for a few minutes before popping the most unexpected question. Being the smartest of the two Soprano siblings, she has been skeptical about her father’s claim that he is just a waste management consultant.
Tony might be evil, but he is arguably one of the most likable TV fathers, and in this instance, sees no point in continuing to lie to his daughter. He admits that a chunk of his income comes from illegal activities but assures her that she ought not to worry about anything. Interestingly, Meadow doesn’t judge him. To her, he is a good parent and that’s all that matters.
10 “I’m like King Midas in reverse. Everything I touch turns to s***.” – Tony in “Isabella”
Tony and Dr. Melfi have multiple fruitful therapy sessions throughout the series and in one of them, the mob boss starts pitying himself. He compares himself to the ancient mythical king, Midas, who was known to convert objects to gold whenever he touched them. However, Tony feels he is a reverse version of the character because most of the things he touches turn out bad.
The clever pop culture reference is a testament to the brilliance of the show. Rather than just make a direct comparison, the story is twisted to suit Tony’s narrative. And it’s understandable for Tony to feel the way he does, given how often things go wrong in his organization. Thankfully, he never suffers a major personal blow.
9 “Tomorrow I can be on time, but you’ll be stupid forever.” – Ralph in “Army of One”
Paulie and Ralph once find themselves in a dispute over $100,000 earned from a heist. Paulie believes he deserves $50,000 because he gave the intel, but Ralph insists on only offering a small amount because he did all the heavy lifting. Tony, therefore, summons the two to solve the issue and when Ralph shows up later, Paulie becomes irate.
Upon noticing Paulie’s mood, the ever-provocative Ralph opts for the most unnecessary yet hilarious insult. He declares that being late is a habit that can be fixed whereas the lack of intelligence (which he feels Paulie suffers from) is permanent. So heavy is the shade that even Tony struggles to hold back his laughter.
8 “Louis Brasi sleeps with the fishes.” – Christopher in “Pilot”
The fictional characters of The Sopranos happen to be big fans of The Godfather trilogy. They talk about it numerous times and among all the references, Christopher’s words in the pilot are the most memorable. This is because he messes up the original quote by Clemenza. After murdering someone, he says “Louis Brasi sleeps with the fishes” instead of “Luca Brasi sleeps with the fishes,” forcing Big Pussy to correct him.
The “sleeping with the fishes” phrase means that someone has been killed, and his body has been dumped in the river. In The Godfather, Luca Brasi gets killed after the narcotrafficker, Virgil “The Turk” Solozzo discovers he is a mole for the Corleone crime family. Christopher doesn’t remember all that, which is ironic because he is shown to be very interested in filmmaking throughout the series.
7 “Qu’est-ce que c’est? Answering machine broken?” – Artie in “Everybody Hurts”
Artie isn’t a tough guy, so he finds himself in quite the dilemma when Jean-Phillipe, the brother of one of his Vesuvio hostesses, avoids his calls after borrowing $50,000 to invest in an alcohol business. He seeks Tony’s help in classic Bonasera-Vito Corleone fashion, but instead of promising to handle the issue, Tony suggests Artie should head over to the man’s apartment and beat him up.
Well, the occasionally comical Artie practices a gangster speech in front of the mirror and then wears black before going to Jean-Philippe’s apartment. There, he attempts to intimidate the man by even infusing some French words but the debtor brutalizes him so much that he leaves with a torn ear. It’s a funny yet pitiful scene that shows just how hard it is to live in the fictional world of The Sopranos.
6 “We’ve got guns here.” – Carmela in “Whitecaps”
Fidelity is not a concept Tony identifies with, so he consistently cheats on Carmela during the first few seasons of the show. Unfortunately for him, his luck runs out when one of his former mistresses, Irina, calls the Soprano house. As fate would have it, Carmela is the one who picks up the phone. A heated exchange occurs in which Carmela threatens Irina, informing her that they are armed, so there is a likelihood she might just come over and shoot her.
This discovery is a major reason “Whitecaps” is considered one of The Sopranos’ best episodes. Before the revelation, Tony and Carmela had even kissed by the sea as they checked out a beach house that he was planning to buy her. After the revelation, the two go on to have one of the tensest arguments in the show, ending in a separation.
5 “A don doesn’t wear shorts.” – Carmine Sr. in “For All Debts Public and Private”
Tony Soprano is very distinguishable from other mob bosses in movies and TV shows because he doesn’t embrace the usual ‘fedora and trench coat’ fashion sense of the Cosa Nostra. He dresses like the average neighborhood and that’s something old-timers like the Lupertazzi crime family boss, Carmine Sr. don’t like.
When he bumps into Tony, Carmine is quick to lecture him. He lets it known that he has heard rumors about the New Jersey mob boss wearing shorts during cookouts and that he finds that unacceptable. This surprises Tony, but he plays it cool to not cause a scene. Well, most viewers would find no fault in Tony’s outfits. In fact, they make him very relatable.
4 “Take it easy! We’re not making a western here.” – Junior Soprano in “Denial, Anger, Acceptance”
Every person in the Cosa Nostra feels compelled to act tough. After all, fellow gangsters are often quick to smell weakness. Mickey Palmice is, therefore, quick to suggest that Junior should whack Christopher after the young mobster offends them. Junior disagrees and even throws shade at Palmice, claiming he is trying to behave like Old West characters in a Spaghetti Western.
Palmice is trying to endear himself to his boss, but Junior can see right through it since he has been in the business for a long time. He and Tony even refer to this behavior as “Cowboy-Itis” during one of their conversations. They find it awkward how everyone tries so hard to look like the toughest person in the room.
3 “Here’s some standard operating procedure… Stay away from Tony Soprano.” – Patsy in “Amour Fou”
Irina isn’t the only one of Tony’s mistresses that ends up getting him in trouble. The car saleswoman, Gloria Trillo, refuses to let go too, and when she starts being psychotic, he sends Patsy to threaten her. The DiMeo crime family accountant pretends to want to test-drive a car and while he is with her, he warns her to back off from the boss.
At first, Gloria is calm. She laughs off Patsy’s threat, informing him that the dealership will send someone to look for her within a few minutes because it’s “standard operating procedure.” Well, Patsy pulls out a gun and issues his own “standard operating procedure,” telling Gloria that from that day onwards, she is never to go near Tony again.
2 “Who do you think you are? Minister of propaganda?” – Hugh in “Proshai, Livushka”
Carmela’s parents, Hugh and Mary, have different personalities. Hugh is generally reserved whereas Mary is talkative and supercilious. It, therefore, comes as a total surprise when Hugh finally responds to something Mary does. It all happens at Livia’s wake where Mary insists on delivering a decent eulogy. Hugh thinks that is nonsense because Livia was very mean. He becomes so annoyed that he describes his wife as the “Minister of Propaganda.”
Hugh is right because anything nice that anyone has to say about Livia counts as total propaganda. According to him, Tony’s late mother never did anything deserving of praise. One can’t help but appreciate how truthful the character is in the scene. His quote is more golden because he deviates from his usual conversations where he keeps reminiscing about his good old days as a soldier stationed in Nova Scotia.
1 “That nose is like a natural canopy.” – Richie in “Full Leather Jacket”
There are several contenders for best insult in The Sopranos, but Richie’s jab at Christopher might just be the very best. During a chat with the up-and-coming hoodlums, Matt and Sean, the Capo jokes that Christopher is the only person capable of smoking a cigarette in the rain with his hands behind his back. And that’s because he has a big nose.
Likening Christopher’s nose to a canopy is indeed men, but Richie is never known for being nice. As the typical tough guy that he is, he cracks the job without smiling or looking at the two junior gangsters. Richie only smiles once during his time on the show. To him, there is nothing to laugh about in life, except his jokes.