Looking Back At ‘The Sopranos’ Most Darkly Comedic Moments

It’s no secret that a big part of The Sopranos’ comes from its dark and often strangely placed sense of humor. While characters brood and life-and-death decisions loom, it remains filled with laugh-out-loud moments. From weighing in on current events, waxing philosophical about life, or making small talk while applying their trade, the show (which is available to stream on HBO Now) never shies away from dark humor. Here’s a look at just a few such moments.

“Nothing. We had coffee.”

In the perfect introduction to Tony Soprano, a casual drive to work during the first episode is interrupted when Tony spots Herman Mahaffey, an insurance agent who happens to owe him some money. As Herman drops his coffee and takes off on foot, Tony chases him through an office park before running him over, looking like he’s having the time of his life all along.

Digging up Emile Kolar

When Christopher keeps having the same nightmare of Emile Kolar, a rival associate he killed as a way to show ambition, he’s afraid he did something wrong when burying him, and grows increasingly paranoid. With the help of Bada Bing bartender Georgie, they dig up the body, only to find his facial hair and fingernails continued to grow. As Christopher states that the fingernails on his hands looked “like a woman’s” its just too much for Georgie to handle.

“You got no idea what ‘dead-eyes’ means until you face these people in your bathrobe and f*ckin’ flip-flops.”

Tony’s friend from high school, sporting-goods store owner David Scatino (Robert Patrick), has a weakness for gambling, and talks himself into an executive game. After digging himself deeper and deeper in debt, Tony and company take over the store for a bust out, maxing out the store’s credit on frivolous purchases until David is bankrupt. When confesses all this to his brother-in-law, who has his own interests in the Soprano family, it’s hard not to chuckle at that line.

“It’s gonna be a while before I eat anything from Satriale’s.”

When an argument between Janice and Richie takes a rather unexpected turn, Janice tearfully calls her brother to help, despite having plotted against him most of the season prior to this moment. After Tony arrives, he enlists the help of Christopher and Furio to help clean up the mess, which takes them to the meat carving room of Satriale’s Pork Store.

“Run that by anti-terrorism. Just for laughs.”

In this episode detailing the F.B.I.’s efforts to place a wiretap in the Soprano home, the family gets limited to the background. As the Feds discuss the schedules of everyone who has a key to the home, including their maid, Agent Harris jokingly suggests they run her husband’s name by anti-terrorism “just for laughs,” proving you don’t need to belong to a family to have a dark wit about you.

“He was an interior decorator.”
“His house looked like shit!”

After a routine collection goes bad, and Paulie and Christopher find themselves hopelessly lost in the woods of Pine Barrens after trying to bury someone who ends up escaping. Reaching out for help, Tony informs them that the man they’re looking for was in the Russian Department of Interior, and basically equivalent to a Green Beret. After misunderstanding Tony’s message thanks to a scrambled cell signal, they give us the now-immortalized dialogue about the state of his home.

“Return to Me”

As the show’s third season approached its finale, Jackie Jr. had just robbed a card game and was now missing. Mis mother, Rosalie, was inconsolable, and Patsy threatened Gloria at gunpoint, telling her to stay away from Tony, who himself was at the center of all of this. As the episode drew to a close, the soundtrack began playing Bob Dylan’s cover of “Return to Me,” an ironic use of a relatively lighthearted ballad in the wake of such severe circumstances.

Christopher’s disastrous intervention

When he descends further into drug addiction, which leads to his car being stolen and beating up Adriana, the family decides to hold an intervention for Christopher. It gets off to a solid start when he remembers Dominic, the moderator, as the guy who stole all those pork loins that time. As they go around the room to talk about his drug problem, Christopher grows increasingly irate, talking back and eventually calling his mother a “f*cking whore.” These being guys not used to talking out their problems, it quickly erupts into a massive fight.

“You know the work I just had done?”

The Sopranos didn’t always limit the fun to New Jersey. When a dispute within the New York family escalates the bodies start piling up, including one of a man who gets shot to death in Phil Leotardo’s trunk. While the murder gets treated as an incidental occurrence, Phil is quick to scold his brother Billy for his carelessness with his car, particularly after just having the car seat replaced.

Paulie and Christopher make amends — after killing their waiter

After Christopher leaves Paulie to pay the check one night, he gets his revenge by running up a $1600 bill on lobster, shrimp cocktails, and by sending a bottle of champagne to a nearby table. As the waiter, who was shorted a tip in all this, confronts them in the parking lot, things go from bad to worse before the waiter ends up shot. The next morning, during a phone call, Paulie offers to bury the hatchet, because in his words, “Life is too short.”

“Any gunshot wounds or broken kneecaps?”

When a late-night car wreck calls into question Adriana and Tony’s “friendship,” Christopher goes off the deep end, causing Tony to take him out on a dirt road and tell him “this is as far as we go.” Tony Blundetto, however, sees another way out. When they confront the doctor who treated Tony after the wreck asking for help he initially refuses, until Blundetto inquires into the specifics of the injuries he’d treated that night, making a veiled, not-at-all subtle threat. By the end, the doctor asks Blundetto if he’s a physician, to which he answers “I’m a pre-board certified massage therapist.”

“There’s no chemical solution to a spiritual problem.”

Drawn to professional writer J.T. Dolan when the two meet recovery, Christopher finds out his new friend has a fondness for gambling, and offers to take his action. After finding himself over his head in debt and unable to pay, Christopher shows up with Little Paulie to show him that this wouldn’t be like Pulp Fiction. After Dolan unsuccessfully tries to pawn his Emmy award, he’s forced to sell his car as a way to make payment. Out of nowhere, Christopher starts playing sponsor, completely ignoring the fact that he put him his friend in this situation in the first place.

The Monopoly brawl

Monopoly leads to violence. It’s a simple fact. So when you take two characters who are already prone to violence (it’s a big part of how they earn their living, after all), factor in long-simmering tensions within their dysfunctional family, then add alcohol, it’s bound to end badly — and it does. Tony keeps taking a joke about Janice too far, causing Bobby to explode with anger, punching his boss in the face, and before long the two nearly take out the entire room while fighting.

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