There are a lot of big personalities on the classic HBO series "The Sopranos," but few captured the minds and hearts of audiences quite like Paulie Gualtieri, aka Paulie Walnuts. With his wingtip hair, bronzed complexion, and pinkie ring, there's no mistaking Paulie, played by real-life former gangster Tony Sirico, for any other mobster. The character provided most of the comic relief on the series, in part because of his many eccentricities. Paulie is a tough, no-nonsense wise guy who also has an obsessive fear of germs, some wild superstitions, and some peculiar habits. Over the course of the series, Paulie went from being a basic enforcer and side character to one of the main characters and mob boss Tony's (James Gandolfini) closest confidante, ultimately surviving long past many others on the series. As such, there are a ton of amazing Paulie moments in "The Sopranos," all made possible by the larger-than-life Sirico and his authentic performance.

The world, unfortunately, lost a legend when Sirico died on July 8, 2022, so to honor his passing and his incredible work on "The Sopranos," I've put together 10 peak Paulie moments. He was a man of many moods and many colorful phrases, and each of these was selected because it shows off what a complex and killer character Paulie was, even when he was being a literal killer.

A Gangster And His Singing Fish

One of the things that makes Paulie such a great character is that he's pretty unpredictable. He's not a wild card like Tony's nephew Christopher (Michael Imperioli), whose weird choices usually end in disaster, but rather is just sort of an oddball. In the season 3 episode "Second Opinion," he tracks Christopher to a run-down motel, where he's cheating on his fiancée Adriana (Drea de Matteo) with a random woman. Paulie followed him to warn him not to be screwing around on Adriana, because "if I can find you, so can your fiancée." Christopher doesn't really appreciate Paulie tailing him or giving him relationship advice, but he mostly brushes it off. Then Paulie reaches into the backseat of the car, and Christopher is suddenly worried, slowly reaching for the pistol tucked into his sock just in case Paulie comes back with a gun of his own. After all, indiscretions and being caught can be deadly for a mobster, and there isn't a ton of trust between Christopher and Paulie.

Instead, Paulie wants to show Christopher his Big Mouth Billy Bass, an animatronic singing fish that was weirdly popular in the early 2000s, when "The Sopranos" was filmed. He's thrilled about the thing, and explains to Christopher that his godson bought it for him and he wants to get one for the club. Christopher is relieved that Paulie just wanted to show him a singing fish and not send him to sleep with the fishes, and it's a great moment of tension release after their brief confrontation.

Throwing Chairs At Ghosts

Paulie is extremely superstitious. He's the kind of superstitious person that won't walk under a ladder and is very nervous around cats, and he makes weird little comments about his various superstitions all the time. His belief in the supernatural comes to a hilarious head early on, however, in the second season episode "From Where to Eternity." After Christopher is shot and his heart stops, he has a vision of hell that he tells Tony and Paulie about upon waking. This understandably freaks Paulie out, and he starts looking for some kind of spiritual answers. His girlfriend suggests that he visit a psychic, and so he does, meeting with a small group of people in the psychic's home to discuss the afterlife. The psychic begins talking to various ghosts around Paulie, naming them as the various people that Paulie has killed over the years. The psychic asks Paulie to leave, and the old gangster finally snaps, throwing a chair at the empty space where the ghosts are supposed to be and yelling a homophobic slur in their general direction.

There's something both extremely funny and sad about a grown man throwing a chair at "ghosts," and it's a great moment that truly shows the weirdness of Paulie's world. He's a tough gangster who isn't ever supposed to show fear, sadness, or any other "soft" emotions, but forcing them inside for his entire life has made him perpetually fearful. He's haunted by guilt, and the idea that his own death could always be lurking around the next corner.

The Tony Napoleon Painting

Paulie had kind of a strange relationship with his boss, Tony Soprano. Paulie doesn't really have a family of his own. His father was non-existent, his real mother turned out to be a nun, the woman who raised him was his aunt and he never quite forgave her for lying, and so he's just a sad, lonely old man. He doesn't have much of a love life and no children (that he knows of,) so the mob has become his family. As such, Tony has become something like a brother to Paulie, and he defers to Soprano with a tremendous amount of respect. There are times when the two don't get along, but Paulie clearly loves Tony, even if he doesn't know how to show it or say it. Tony, for his part, cares about animals more than people, and his greatest love is probably a racehorse named Pie-O-My. Tony even had a painting of himself done with the horse, but when she dies in a stable fire, he never wants to see the painting again.

Instead of chucking the painting, Paulie has the artist paint Tony like a general (he looks a lot like Napoleon) and puts it above his fireplace. In the season 5 episode "All Due Respect," Tony visits Paulie at home and discovers the painting. He's initially furious, and demands to know why he both kept it and painted him like a general. Tony had ordered the painting burned, but Paulie explains:

"But I told the guys, the chance to hang a picture of you on my wall? I rescued it from the flames."

When Tony reminds Paulie how much it upsets him to see the horse, Paulie tells Tony that he doesn't come around anymore, so he didn't think it would be a problem. There's real sadness in Paulie's voice, and Sirico plays the part of a kicked puppy surprisingly well. He loves and misses Tony, and even if there are good reasons to avoid one another, like law enforcement tailing them, he wants to remind himself of his mafia "family."

'Remember Pearl Harbor.'

Paulie was not a well-educated man, having dropped out of high school to engage in various nefarious activities. His understanding of the world is rather skewed, and this lack of education tends to reinforce some of his more ignorant beliefs. While the character is certainly lovable for being funny and having a lot of emotional depth in later seasons, he's also a racist, sexist, homophobic dinosaur who runs his mouth and says some awful things. Thankfully, his ignorance is also occasionally hilarious when he tries to sound smart and ends up exposing his stupidity.

One great example of this is in the season 5 episode "Sentimental Education," when recently released felon Tony B. (Steve Buscemi) is talking to the crew about his Korean boss, Mr. Kim. Paulie offers a bit of advice, saying "word to the wise: remember Pearl Harbor." Not only is Paulie completely off-base because Japan attacked Pearl Harbor in 1941, not Korea, but his advice would make zero sense even if it was relevant. It's just an excuse to be racist and write someone off for being different, which unfortunately Paulie proves to be pretty good at. It's honestly even worse because Paulie was in the Army Signal Corps for a few years, so you think he might have learned a bit of military history. Apparently not.

Getting Kicked In The Walnuts

Being a mafia enforcer can be violent business, and Paulie knows that just as well as any of the other wiseguys. He's involved in quite a few murders over the course of the series, but the most poorly executed one happens to be the most entertaining. In the season 6 episode "Mayham," Paulie and one of his crew go to steal from a gang of Colombians under the assumption that the hideout is empty. Unfortunately, there are still quite a few gangsters lurking about, and Paulie gets into a nasty fight with one of them bearing a massive knife. Paulie's doing alright for himself until he gets kneed in the groin and collapses to the ground, clutching his testicles.

Seeing Paulie go from consummate badass to crying baby in a matter of seconds is pretty funny, but his bleating of "my bawls!" makes it even better. He ends up stabbing the guy that gave him a nut-shot after his partner shoots him, and then continues to roll around on the bloody kitchen floor, clinging to his crotch and groaning. I know getting kicked in the nads hurts, but seeing that tough persona crumble is comedy perfection.

Getting A Good Base

Paulie is a very particular man, and he deeply cares about how others view him. His hair is almost always perfectly swooped, his face clean-shaven, his clothes pressed and ironed. He's a stickler for appearances, and that expands to his love of suntanning. Throughout the series, we see Paulie sitting out in front of Satriale's pork store with a reflecting screen, trying to get a deep suntan. Skin cancer isn't really a concern for the gangster, since very few people in his line of work live long enough to worry about something like that, and he wants to make sure he looks good.

One of the first times we see Paulie with his shades on and foil reflector in full glory is in the season 2 episode "House Arrest," where he gets to tanning while Tony smokes a cigar after they witness a car accident across the street. The tanning is just one of Paulie's many little peculiar traits, and it makes him a much more three-dimensional character than the average TV or movie mobster.

Tough Love For Christopher

The crew really comes together for Christopher in the season 4 episode "The Strong, Silent Type," when the whole mob family teams up to give him an intervention for his drug use. Christopher has a serious heroin habit, and after showing up to Tony's mother's wake high, messing up his mob duties, and sitting on Adriana's dog and killing it, everyone has had enough. The therapist they've hired to help with the intervention asks people to read statements that they've written to Christopher, and some of them are incredibly heartfelt. Even Sylvio (Steven Van Zandt) reads from a little scrap of paper, being as earnest as a man in a toxic masculine culture can. Tony, for his part, is most upset about the dog. Then we get to Paulie, and he has a very different kind of pep talk for Christopher:

"I don't write nothin' down, so I'll keep this short and sweet. You're weak. You're outta control. And you've become an embarrassment to yourself and everybody else."

This gets things a bit heated, and Paulie is reminded that this is supposed to be a "non-judgmental" intervention, but Paulie isn't having it. He says that Christopher needs to "take his medicine," and it's brutal. The scene is difficult because it's easy to understand everyone's feelings and frustrations; Paulie is being this hard on Chrissy because he loves him. If he didn't, he would have just figured out a way to get rid of him a long time ago, Tony's nephew or not. It's not the right thing to do, but it's the Paulie thing to do, and it's a great demonstration of how sometimes characters in this series show love by being hurtful.

Annoying Tony To Death – Literally

Sometimes Paulie's need for attention, validation, and love can be so intense, it can drive a man into tachycardia. In the season 6 episode "Mayham," Paulie goes to visit Tony in the hospital (after his testicles have recovered, of course.) Tony is in a coma after being shot by Uncle Junior (Dominic Chianese), and the whole crew turns out to visit him in shifts. While Paulie visits, he begins complaining to the unconscious Tony about his own health problems, including the fact that his doctor wants him to start wearing a jock strap. He explains that when he was in the Army, he won the "chin-ups" three times in a row, and he used to be fit as a fiddle. As he gets more riled up, Tony's heartbeat starts to rise, eventually going into a full-blown heart attack. Whether that was a result of Paulie's antagonistic ramblings, the chaos going on in Tony's coma dream, or it's all just a coincidence, we'll never know.

What I do know is that it sure looks like Paulie Walnuts almost annoyed the boss to death, because even the hell Christopher envisioned was better than listening to Paulie continue to rant.

The Entirety Of Pine Barrens

It's almost impossible to pick a favorite moment from the season 3 episode "Pine Barrens." The episode is one of the best in the series, following Paulie and Christopher after they think they've killed a Russian man they were supposed to collect money from. The two practiced killers immediately wrap him in a rug and head out to the woods to get rid of the body; the problem is that the Russian is still very much alive. He ends up escaping and Paulie and Christopher try to catch him but end up getting lost in the woods themselves. The episode is an excellent mix of the series' dark humor and harrowing moments and highlights the complicated relationship between Paulie and Christopher. The two are constantly at odds, and being forced to try and survive together is a perfectly particular divine punishment. It's hell for the guys, but it's a whole lot of fun to watch.

If there's one moment in "Pine Barrens" that somehow stands above all of the others, it's when the duo manage to find their way back to the car and discover some ketchup packets. Starving after being out in the snow searching for the Russian, they start slurping at the ketchup like it's manna from heaven. It's not dignified, but hey, a man's gotta eat.

That Darn Cat

Many of the made men on "The Sopranos" never made it to the end of the series, but somehow Paulie outlasted them. Despite a prostate cancer scare and plenty of close calls, Paulie managed to survive until the very end. The specter of death was always there, however, and one of his superstitions made him even more paranoid. After Christopher's death, an orange cat starts hanging around Satriale's and staring at Chrissy's photo. The cat really creeps out Paulie, who believes they're cursed creatures, and he begs Tony to get rid of it. Tony, being a softie on animals, refuses.

Paulie's final scene on "The Sopranos" is also one of his best. In the series finale, "Made in America," Paulie and Tony have a chat about the future and Paulie reassures his boss that he will always be there for him. Tony leaves and Paulie sets up his foil to get a little sun, completely oblivious that the cat is approaching. It ends up laying down right in front of the doors to Sal's, sunbathing just as surely as Paulie is. The cat represents everything negative in Paulie's life, encasing all of his guilt, paranoia, and fear into one furry feline. The fact that it appears in his final scene is just a reminder that Paulie will never know peace. He will always be haunted by the past and nervous about an uncertain future. His ignoring the cat means that either he's learning to live with it, or, more likely, he's completely unaware of his own demons.

Tony Sirico made Paulie one of the greatest characters in television history, imbuing him with humor and authenticity that will live on as long as people have access to "The Sopranos." Rest in peace to a real one, and God bless Paulie Walnuts.

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