25 Best Quotes from The Sopranos

Was Carmine Lupertazzi Jr. secretly a genius? Or was he just not well-spoken? Either way, this infamous quote reignites a dangerous feud between the New Jersey and New York mobs. After the deaths of Billy Leotardo and Anthony Blundetto, as well as the disappearance of Vito Spatafore, Carmine attempts to hold a remedial meeting before anyone does anything drastic. In a morbidly hilarious turn of events, however, Carmine refers to Phil’s brother’s death as “whatever happened there.” Unfortunately, the meeting immediately goes up in flames, much to the curse-laden chagrin of Tony.

What Makes It Great?

Aside from cementing Carmine Lupertazzi Jr. as an ineffective leader, this scene would be instrumental for the final conflict found in the last season. It confirms that Phil will never let go of his brother’s death, justifying his future conflicts with the New Jersey mob and the series of killings that would follow. Some have even speculated that Carmine purposefully tanked the meeting as a way to ensure war between the two families. Whatever Carmine’s intentions were, Ray Abruzzo’s nonchalant delivery makes this unexpected quip all the more memorable.

24Christopher Moltisanti in Season 5, Episode 6, “Sentimental Education”

“Other people’s definitions of you, sometimes they’re more about making themselves feel better. You gotta define yourself.”

Christopher Moltisanti was a genuinely broken character for most of the show, yet he outlasted some of the cast’s most colorful characters. A self-conscious person, Chris was always aware of his failings, especially after delivering this truth bomb in the episode “Sentimental Education.” The episode has a large focus on Tony Blundetto, Tony Soprano’s cousin, as he attempts to readjust to a civilian lifestyle. After a particularly bad day at work, Christopher tries to cheer Blundetto up with his own optimistic advice — even if Blundetto eventually gives in to his criminal ambitions by the end of the episode.

What Makes It Great?

Although mostly rugged around the edges, enslaved to his addictions and dysfunctional life, Christopher was a creative soul who sought to find his path numerous times. Tony Soprano would always support him or dig him out of the holes he caved in for himself until he had enough of his erratic behavior. Seeing Christopher extend the same hand to Tony Blundetto showed a genuinely sympathetic side of his character we only get to see every so often.

23Tony Soprano in Season 1, Episode 13, “I Dream of Jeannie Cusamano”

“What kind of person can I be, where his own mother wants him dead?”

Livia Soprano was her son’s worst nightmare. An early widow, Livia resents both their children for leaving the nest too early to escape her. While Janice was smart enough to go as far away as possible, Tony stuck close to home to watch out for her. Livia had a cunning silver tongue that got Tony into one too many confrontations with the members of his own family, especially with his Uncle Junior. This is made especially apparent in “I Dream of Jeannie Cusamano,” where Tony is nearly killed in a shootout. After sorting out the incident, he finds out his mother manipulated the events that led to his near death, making the boss question his worth as a human being, given how his mother wants him dead.

What Makes It Great?

This key moment in season one would have massive ramifications throughout the rest of the series. Tony’s relationship with Livia would be forever altered for the worse, and though Uncle Junior’s involvement could be chalked up as part of the business, Tony would never really feel the same afterward. Even though Nancy Marchand would, unfortunately, pass away sometime between seasons two and three, her cunning performance as Livia would linger throughout the rest of the series.

22Dr. Jennifer Melfi in Season 1, Episode 4, “Meadowlands”

“Sometimes it’s important to give people the illusion of being in control.”

The talks between Tony and Dr. Melfi makes for some of the best moments in the show, especially since we see Tony explaining the nuances of his business to Melfi without actually telling her what he does for a living. One of the critical aspects of these therapy sessions is Tony’s reluctance to forfeit control of everything in his life, with Melfi attempting to guide him on ways to delegate or compromise. She makes a point of letting him know that in his line of work, sometimes letting people think they are getting what they want can be more crucial to moving forward instead of trying to come out on top of every situation.

What Makes It Great?

Being the all-controlling force he is, Tony Soprano uses the illusion of control as a means to not only keep himself safe but to put down his potential enemies. Tony convinced Junior Soprano to take over as head of the family, for example, so that Junior would take the fall when the feds finally got the slip on them. Tony would later utilize this very same idea to put Feech La Manna back in prison after entrusting him with a batch of stolen televisions. Though Tony would often make his actions plainly known, he was just as capable of subterfuge as well.

21Carmela Soprano in Season 4, Episode 13, “Whitecaps”

“More is lost by indecision than by wrong decisions.”

20Tony Soprano in Season 6, Episode 1, “Members Only”

“I don’t care how close you are: in the end, your friends are gonna let you down. Family. They’re the only ones you can depend on.”

All mob-related media have one thing in common that rings true to the real-life dealings of the mafia: you never trust outsiders; you can only count on your family. That’s a lesson Tony tries to teach A.J. when he comments on his father’s social habits and general mistrust of people. It’s important to remember that this quote comes from the beginning of season six, arguably the bleakest season of the entire series. Johnny Sack is in jail, Adriana is dead, and by the end of the episode, Uncle Junior nearly kills Tony in a case of mistaken identity. The very “family” that Tony relies on so much is shrinking with every passing year.

What Makes It Great?

While the words spoken by Tony can ring true in many family circles, sometimes we are better off building a family of our own with the friends we make along the way. However, we must remember Tony’s upbringing, as he never knew anything outside the inner circle that surrounded him in his adult years. Consider how this quote affects Eugene as well, the other main focus of the episode. After years of loyalty to Tony, a sudden influx of cash presents an opportunity to peacefully retire to Florida — until Tony immediately shoots that plan down. With Eugene stuck in New Jersey pending his status as an FBI informant, he too finds that one of his biggest “friends” will ultimately let him down, leading to his untimely demise.

19Silvio Dante in Season 4, Episode 12, “Eloise”

“You are only as good as your last envelope.”

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 the 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 he doesn’t need to suck up to anyone. All he has to do is earn more.

What Makes It Great?

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. In fact, Ralph would bring up that very same sentiment during a vicious brawl between the two earlier in the season — prior to being killed by Tony Soprano, of course.

18Paulie Gualtieri in Season 3, Episode 11, “Pine Barrens”

“The guy was an interior decorator. He killed 16 Czechoslovakians.”

In just about every episode, Paulie “Walnuts” does something 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 as a Russian Interior Ministry operative, but poor reception garbles his words. Instead, Paulie misinterprets it as him being an “Interior Decorator” who killed 16 Czechoslovakians. Christopher, confused, remarks that his house “looked like s***.”

What Makes It Great?

“Pine Barrens” is one of the few times The Sopranos would veer into outright comedy. 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. In a way, it shows his complete trust in Tony, despite presumably being told a complete non sequitur. On top of that, Christopher’s befuddled reaction makes the ludicrousness of the quote all the more hilarious, especially when you consider just how messy Valery’s home was.

17Junior Soprano in Season 5, Episode 3, “Where’s Johnny”

“He never had the makings of a varsity athlete.”

There are only a few things Junior enjoys more than stepping on Tony’s toes. During one Sunday dinner, he does so again, telling everyone that his nephew never had what it took to be a varsity 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 has said these words. In the prequel movie, The Many Saints of Newark, a younger Junior is shown making the same remark, infuriating Tony in the process.

What Makes It Great?

It’s easy to see why Tony gets so furious because the words remind him that there is something he isn’t good at. There’s a good chance that he would have had a more honorable career if he wasn’t so unruly and undisciplined. This quote also comes at a point in the series where Junior’s dementia is starting to more visibly show itself, with Tony’s ignorance of his condition gradually building to an unfortunate payoff.

16Bobby Baccalieri Jr. in Season 4, Episode 1, “For All Debts Public and Private”

“You know Quasimodo predicted all this.”

Some of The Sopranos‘ funniest scenes come completely out of left field. For example, take this infamous quote from fan-favorite Bobby Baccalieri as he sits down to eat with Tony at a greasy diner. The two muse over Bobby’s pending promotion from Junior Soprano. As the conversation steers into mortality, Bobby lets out this infamous phrase to an immediate confused reaction by Tony. Nostradamus is then confused for Notre Dame, to which Bobby gives an indifferent shrug as he conflates football with the end of the world.

What Makes It Great?

As funny as the scene is, this brief exchange also relates to some of the greater themes discussed throughout the rest of the series. Mortality and fate are two common fixtures of the series, and knowing the ultimate fate of Bobby barely two seasons later — in addition to what eventually happens to Tony — there’s a smidgen of eeriness to be found in Bobby’s attempt at philosophy.

15Phil Leotardo in Season 6, Episode 20, “The Blue Comet”

“Let me tell you a couple of three things.”

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 his enemies’ three major sins: the deaths of Coco, Fat Dom, and Billy Leotardo.

What Makes It Great?

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 had 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.

14Meadow Soprano in Season 1, Episode 5, “College”

“Dad, are you in the mafia?”

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. 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.

What Makes It Great?

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. The question of Tony’s mob ties being revealed to his family would come up eventually, and addressing it in such a matter-of-fact way would open the door to more interesting stories with each successive season. For example, the ill-gotten gains that Tony speaks of in this very episode would eventually make their way straight to A.J. and Meadow.

13Tony Soprano in Season 1, Episode 12, “Isabella”

“I’m like King Midas in reverse. Everything I touch turns to s***.”

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 badly. It’s important to note that the quote comes after the onset of his numerous panic attacks, the deaths of Brendan and Mikey, and most importantly, a potential Attention Deficit Disorder diagnosis for A.J. Thankfully, he never suffers a major personal blow.

What Makes It Great?

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. Knowing how he feels for A.J. specifically, that Tony’s “rotten, putrid genes” may have infected him, he feels especially morose. Tony’s self-hatred would, in some ways, present itself in A.J. throughout the series, slowly escalating with each successive season.

12Ralph Cifaretto in Season 3, Episode 13, “Army of One”

“Tomorrow I can be on time, but you’ll be stupid forever.”

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.

What Makes It Great?

Ralph’s tenure on The Sopranos was loaded with button-pushing antics like this. Joe Pantoliano, who played Ralph, has a way of genuinely getting under your skin, combining Ralph’s sadistic tendencies with some of the most cruel jokes in the entire series. That’s not to say that the constant ribbing doesn’t add up, however. As funny a moment as this is, it’ll set the stage for Ralph’s increasingly reckless behaviors that put his ability to earn money at risk. Another joke involving Ralph and the wife of Johnny Sack would even play into a major conflict found throughout season four.

11Christopher Moltisanti in Season 1, Episode 1, “Pilot”

“Louis Brasi sleeps with the fishes.”

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” Salvatore Bonpensiero to correct him. Funnily enough, only one season later, Big Pussy would sleep with the fishes himself.

What Makes It Great?

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. Then again, malapropisms are commonplace throughout The Sopranos. Just take a look at the “sacred and profane” Carmine Lupertazzi Jr.

10Salvatore Bonpensiero in Season 2, Episode 13, “Funhouse”

“Anyway, four dollars a pound.”

Speaking of fish, we’d be remiss if we excluded a meme-worthy quote from one of the best episodes of The Sopranos, “Funhouse.” When Tony is suffering from a bout of food poisoning, his day is in shambles as he drifts in and out of uncomfortable fever dreams. In one of the most memorable sequences of the show, Tony’s dream sees him happily walking down a boardwalk before entering a disjointed discussion with a familiar-sounding fish. Turns out, the fish is actually Salvatore Bonpensiero. The two briefly crack wise with each other before the tone suddenly shifts. A suddenly defeated-sounding Salvatore quickly declares that it’s “four dollars a pound,” before hammering in what Tony feared about his longtime friend for so long.

What Makes It Great?

This scene is crucial for Tony in that it forces him to confront what he already knew was true: that Sal flipped, and that he’s currently feeding everything he knows to federal officials. The sequence itself is equal parts eerie and hilarious, made more effective by the limited use of CGI to animate Sal’s mouth. It’s also thematically appropriate, as in the same episode, Tony finally makes the decision to take Sal out to sea with a few of his friends — only to put him down and leave him sleeping with the fishes. It’s definitely one of the most surreal Sopranos moments, especially when coupled with Tony’s other supernatural dreams.

9Artie Bucco in Season 4, Episode 6 of “Everybody Hurts”

“Qu’est-ce que c’est? Answering machine broken?”

Artie isn’t a tough guy, so he finds himself in quite a 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. Fortunately, the cold-blooded Furio is able to lend a hand later in the episode.

What Makes It Great?

It’s a pitiful, but incredibly funny scene that shows just how hard it is to live in the fictional world of The Sopranos. Despite coming off as weak throughout the whole ordeal, however, it’s moments like this that show the genuine strength of Artie as a person, made all the more believable by John Ventimiglia’s performance. You have to remember that this is far from an isolated incident. Artie points a gun directly at Tony’s head after learning about the fate of his first restaurant, and he later beats down Benny for using Vesuvio in one of his criminal escapades. Considering everything that’s happened to Artie, his ultimate fate in the series is one of the few times you’ll get a happy ending.

8Carmela Soprano in Season 4, Episode 13, “Whitecaps”

“We’ve got guns here.”

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. By this point, Carmela has gotten so fed up with Toy’s lies and infidelity, there is a likelihood she might just come over and shoot her. Carmela finally reached her ultimate breaking point, cementing her status as one of the best women characters in a mafia series.

What Makes It Great?

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 on the show, a full-on screaming match even, before ultimately ending in a separation. It would completely change the dynamic of Tony’s family relationships for the rest of the series.

7Carmine Lupertazzi Sr. in Season 4, Episode 1 “For All Debts Public and Private”

“A don doesn’t wear shorts.”

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 dad 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.

What Makes It Great?

Most viewers would find no fault in Tony’s outfits. In fact, they make him very relatable. The Sopranos was revolutionary in that it not only de-glamorized the mob lifestyle, but it also presented a protagonist who was far removed from the legendary Don Correleone of The Godfather. Tony Soprano is, for all intents and purposes, a don that wears shorts: a criminal overlord whose wealth and sinful vices are contrasted by an open bathrobe and fuzzy slippers. You could even argue that this degree of relatability would open the door for future criminal protagonists like Breaking Bad‘s Walter White or The Shield‘s Vic Mackey.

6Tony Soprano in Season 4, Episode 9, “Whoever Did This”

“She was a beautiful, innocent creature! What did she ever do to you?”

Season four of The Sopranos is loaded with incredible quotes, due in part to the psychotic antics of Ralph Cifaretto. Acting as one of the season’s antagonists, Ralph increasingly gets on Tony’s nerves with his escalating mistakes. After wounding a member of the crew, murdering an innocent woman named Tracee, and (presumably) burning Tony’s prized racehorse alive for the insurance money, Tony screams this quote at Ralph as he beats him to death following a tense argument. Whether Ralph really did kill Tony’s horse is never really answered. Afterward, Tony and a visibly-under-the-influence Christopher dispose of Ralph the best they can.

What Makes It Great?

The ambiguity of the scene, especially the quote itself, is what makes it so great. Some have theorized that instead of Tony’s horse, Tony may actually be referring to Tracee. Otherwise, it’s yet another showcase of Tony’s love of animals, a reoccurring aspect of his character ever since he tended to a family of ducks in the first season. It remains one of Tony Soprano’s best quotes, not only for the context in which it’s said but for the emotionally-charged delivery provided by James Gandolfini. It’s a scene you can’t help but rewatch over and over again.

5Junior Soprano in Season 1, Episode 3, “Denial, Anger, Acceptance”

“Take it easy! We’re not making a western here.”

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 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.

What Makes It Great?

It’s especially interesting to see Junior say something like this, given how many Western references can be found in the series. Aside from Tony’s frequently-stated admiration of Gary Cooper, who famously portrayed a number of stoic characters in Westerns, the theme from The Good, the Bad, and the Ugly can be heard in passing during a brief scene in “Fortunate Son,” and references to Western legends like Roy Bean can be found throughout the series.

4Patsy Parisi in Season 3, Episode 12, “Amour Fou”

“Here’s some standard operating procedure… Stay away from Tony Soprano.”

Irina isn’t the only one of Tony’s mistresses that ends up getting him in trouble. The car sales agent, Gloria Trillo, refuses to let go too, and when she starts pushing Tony’s boundaries, 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 onward, she is to never go near Tony again.

What Makes It Great?

Patsy isn’t a character we see very often, making his sudden, violent threat feel all the more uncomfortable. It’s a reminder that Tony is, at the end of the day, a mob boss. He won’t get his hands dirty unless he absolutely has to, since he’ll have plenty of underlings to do it for him. The bluntness of his violent threat ties into one of the series’ biggest strengths as well. The Sopranos initially drew significant controversy for painting Tony as an outright villain, starting all the way back in season one’s “College.” Gloria’s depressing spiral following this scene only compounds just how cruel The Sopranos could truly be.

3Hugh DeAngelis in Season 3, Episode 2, “Proshai, Livushka”

“Who do you think you are? Minister of propaganda?”

Carmela’s parents, Hugh and Mary, have different personalities. Hugh is generally reserved, whereas Mary is talkative and supercilious. Therefore, it 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 of Livia’s manipulative and cunning personality. He becomes so annoyed that he describes his wife as the “Minister of Propaganda” before jumping into a hushed tirade.

What Makes It Great?

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. It’s rare to see him show so much emotion elsewhere.

2Richie Aprile in Season 2, Episode 8, “Full Leather Jacket”

“That nose is like a natural canopy.”

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, Richie 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 Christopher has a big nose. Matt and Sean laugh it up as they try to avoid stepping on Richie’s toes. Unfortunately, their failed attempt at a hit on Christopher later in the season ultimately breaks the trio’s tenuous relationship for good.

What Makes It Great?

Likening Christopher’s nose to a canopy is indeed mean, but Richie was never known for being nice. His repeated beatings of Beansie and morbid wisecracks after the fact are a testament to this. Like the typical tough guy that he is, he cracks the jab without smiling or looking at the two junior gangsters. Richie only smiles once during his time on the show — there is nothing to laugh about in his life, except his jokes. It’s moments like this that make season two one of the best seasons of The Sopranos, period.

1Livia Soprano in Season 1, Episode 2, “46 Long”

“Oh, poor you!”

Arguably the most instrumental character in the early seasons of The Sopranos, Livia Soprano has had her fair share of morbid zingers throughout her brief run in the series. From as early as the second episode in season one, “46 Long,” she establishes herself as a blatantly negative influence on Tony Soprano’s life. Following an argument over whether Green Grove is a nursing home or a “retirement community,” Tony voices his concerns about her increasingly negative disposition towards anyone and anything in her life. Livia had only one thing to say in response: “Oh, poor you!”

What Makes It Great?

In as little as three words, Livia establishes several key ideas that would be present throughout the rest of The Sopranos. It establishes her bleak outlook on life, Tony’s developing depression, and an overall negative relationship that continues to affect Tony even after her departure in season three. It would also be a terrifying quote that Tony himself channels as he spirals into his depression and self-destructive behaviors towards the latter half of the series.