The Sopranos’ Funniest Moments

Alongside the violence and mobster intrigue, HBO crime drama The Sopranos never lost sight of life’s funnier moments…

The Sopranos’ genius was in telling structured stories with well-established themes, while still aping life in all its dirty, disorganised, contradictory, open-ended glory. The show wasn’t a drama, or a comedy, or a tragedy, or a farce. It was all of them. It was none of them. It was life.

Creator David Chase and his crack team of writers never lost sight of the essential truth that no matter how cruel, harrowing or horrid life becomes, it’s always laced through with laughs: oftentimes the laughter and the horror rise in tandem.

Here, then, are some of The Sopranos’ funniest moments, most of them enmeshed with the macabre, the monstrous and the melancholy. 

South of the Border

S1, E9 ‘Boca’

The Sopranos season 1 episode 9

In the machismo-drenched world of the mafia, even going down on your girlfriend is seen as a sign of sexual weakness, and quite possibly – in the non-PC words of Uncle Junior himself – ‘a sign that you’re a fanouk.’

Ad – content continues below

Apparently, ‘they’ think ‘if you’ll suck p***y, you’ll suck anything.’

Whoever ‘they’ are.

News of Uncle Junior’s oral talents reaches Tony from a gossip chain, the final link in which is Carmella. Tony’s reaction, and the way in which he baits Uncle Junior with the intel on the golf course (culminating in Tony singing ‘South of the Border, down Mexico way’) is equal parts childish to hilarious – but funniest of all is how this schoolboy teasing serves as the pre-cursor to a Mafia war.

As Tony later tells Carmella: ‘Cunnilingus and psychiatry brought us to this.’     

Guess Whose Back?

S1, E10 ‘A Hit is a Hit’

The Sopranos season 1 episode 10

Christopher sets Adrianna up in a recording studio to help realise her dream of becoming a music mogul. Things don’t go well. Her new band – the woeful Visiting Day – is ready to walk after a long and soul-sapping session during which they’ve produced nothing of worth. Christopher wastes no time taking up the mantle of manager to convince them that the show must go on. It’s fair to say that being motivational doesn’t come naturally to Christopher. Or, rather, it does, it’s just that his methods of motivation are rather more violent than most. First, Christopher throws the ex-addict lead singer a bag of crystal meth and orders him to take it. When that doesn’t work, he takes the only reasonable course of action left open to him and smashes a guitar over the man’s back.

There’s No Place Like Home

S2,E4 ‘Commendatori’

The Sopranos season 2 episode 4

Paulie is incredibly excited to be visiting the motherland, and arrives full of romantic notions about Italy. All of these are systematically stamped out, mostly by Paulie himself, of whom an Italian gangster remarks at dinner, after Paulie requests tomato ketchup for his spaghetti:  ‘And you thought the Germans were classless pieces of shit.’

Ad – content continues below

Paulie’s beatific little smile as he drinks in the squalor of New Jersey on the ride home from the airport is pitch perfect.

It’s the Jaaaccckkeett!

S2,E8 ‘Full Leather Jacket’

The Sopranos season 2 episode 8

From the moment Richie Aprile is released from prison he’s on a collision course with Tony. In classic Sopranos’ style, though, the torch paper isn’t lit by Richie shacking up with Tony’s sister, or paralysing their mutual friend Beansie, but by the fall-out from a spurned jacket. Not just any jacket, though: ‘the’ jacket; the one Richie took off Rocco di Meo after an adolescent scrap.

‘Cocksucker had the toughest reputation in Essex County, but he never came back after I got through with him,’ Richie tells Tony, as he gifts him the infamous garment.

‘He later died of Alzheimer’s,’ adds Junior.

The look on Tony’s face as he tries to look grateful for ‘the jacket’ is almost as funny as the look Richie later wears in Carmella’s kitchen when he  notices the sainted jacket hanging from the shoulders of the maid’s husband.

I Ain’t Afraid of No Ghost

S2, E9 ‘From Where to Eternity’

The Sopranos season 2 episode 9

When Christopher briefly dies on the operating table after an assassination attempt, he returns from the brink of death with visions and dispatches from the afterlife. Paulie takes these reports to heart, divining in them a supernatural threat. Not only does Christopher tell Paulie that the souls of his many victims still follow him everywhere he goes, he also brings back an oblique warning: ‘Three o’clock’.

Ad – content continues below

This cryptic curse has Paulie slamming bolt upright in his bed each night with a scream on his lips. First he visits Tony, who tries to lead Paulie back to sanity.

‘You eat steak?’ Tony asks.

‘What the fuck you talkin’ about?’

‘If you were in India, you would go to hell for that.’ 

‘I’m not in India,’ says Paulie. ‘What do I give a fuck?’

‘That’s what I’m trying to tell you. None of this shit means a goddamn thing.’

Ad – content continues below

Unconvinced, Paulie visits a spiritualist psychic, who ‘confirms’ that Paulie is being stalked by ghosts. ‘That’s satanic black magic!’ rails a terrified Paulie, ‘Sick shit’, before hurling a chair at the ‘ghosts’ and screaming ‘Fuckin’ qu***s!’ at them. Finally, he visits his priest to tell him he’s cutting off his donations to the church on the grounds that he should’ve been protected from hauntings. I defy you not to chuckle at the baleful glare Paulie gives the Virgin Mary on his way out of the church.  

A Very Un-woke Wake

S3, E2 ‘Proshai , Livushka’

The Sopranos season 3 episode 2

Livia Soprano – Tony’s murderously manipulative mother – proved just as divisive in death as she was in life, her demise precipitating a wake that was as awkward and corrosive for the characters experiencing it as it was rich and funny for us schmucks at home.

Tony never wanted any of Janice’s ‘California Bullshit’ at the gathering he and Carmella hosted at their home (or ‘that house, up on that hill’, as Livia would have called it). Janice being Janice, though, vetoes her brother’s ruling. She asks each of the assembled guests to share a thought, a memory of their mother, which – given that Livia was a sharp-tongued, anti-social harridan – doesn’t produce heart-warming results. No wonder the unknown man descending the stairs in the background behind them all decides to about-turn and get the hell out of there.

‘She never minced words,’ says Hesch, trying his hardest to accentuate the positive, ‘Between… brain and mouth… there was no interlocutor.’

Christopher’s rambling, drug-fuelled, ad lib on the nature of existence, rebirth and doppelgangers is a treat, the sort of new-age snash David Brent might have conjured up while fully sober. The silence doesn’t last for long, though, not least because Carmella has spent the duration of the tense memorial knocking back booze like a cooze-hound on Spring Break, and is ready to unleash hell. 

Merry Stressmas

S3, E10 ‘…To Save Us All from Satan’s Power’

The Sopranos season 3 episode 10

In the absence of Big Pussy Bonpensiero – taken on a long boat-ride to oblivion – the amply proportioned Bobby Baccala is the natural choice to become the new Satriales’ Santa. Except he doesn’t want to do it. He’s too shy.

Ad – content continues below

‘The fucking boss of this family told you you’re gonna be Santa Claus,’ Paulie tells Bobby menacingly. ‘You’re Santa Claus. So shut the fuck up about it!’

The surly and reluctant Bobby proves a lacklustre substitute, an observation that’s articulated perfectly by Paulie when he says, ‘Fuckin’ ho hum if you ask me.’

It’s not just Bobby’s mafia colleagues that like to drop the F-bomb at Xmas. Even a little boy, unimpressed by Bobby’s schtick, issues a heart-felt: ‘Fuck you, Santa.’

God bless us. Every one. 

Two Assholes Lost in the Woods

S3, E11 ‘Pine Barrens’

The Sopranos season 3 episode 11

The Pine Barrens was the episode that cleaved most closely to all-out comedy, pitting hot-headed anti-survivalists Christopher and Paulie against a runaway Russian they’d failed to kill. The darkly comic shit-show unfolded in the unforgiving, snow-filled foliage of the eponymous Pine Barrens, where Tony and Bobby were eventually summoned to rescue the hapless pair.

It’s hard to pick a comedy highlight from this episode, as it’s chock-full of them, but highlights include Tony losing it at the sight of Bobby Baccala’s hunting attire (if James Gandolfini’s laughter seems particularly genuine here, try googling some behind-the-scenes facts – you won’t be disappointed); Chris and Paulie noshing down on sauce sachets like they were a gourmet meal, and the following misunderstanding between Paulie, Chris and Tony thanks to poor mobile reception:

Ad – content continues below

Tony: (garbled, on phone) It’s a bad connection, so I’m gonna talk fast. The guy you’re looking for is an ex-commando! He killed sixteen Chechen rebels single-handed.

Paulie: Get the fuck outta here.

Tony: Yeah, nice, huh? He was with the Interior Ministry.  Guy’s some kind of Russian green beret. This guy cannot come back to tell this story. You understand?

[line breaks]

Paulie: (to Christopher) You’re not gonna believe this. He killed sixteen Czechoslovakians. The guy was an interior decorator.

Chris: His house looked like shit.

Ad – content continues below

You Talkin’ To Me?

S4, E6 ‘Everybody Hurts’

The Sopranos season 4 episode 6

Artie Bucco, Tony’s boyhood best pal, is a regular, hard-working chef. Even so, he’s frequently seduced by the luxurious criminal lifestyle he sees lapping around the fringes of his wonder-bread world. When a business deal to promote ‘the new French vodka’ goes awry and Artie finds himself $50k out of pocket to a swindling huckster he decides to channel his inner Mafioso and get his money back the Soprano way. Unfortunately, his inner Mafioso is no more ferocious than that possessed by any average member of the show’s audience – as much as proximity to Tony might convince us otherwise – and he gets the crap kicked out of him. Before that, though, his little Taxi Driver moment in the mirror, complete with mid-life crisis ear-ring and mobster posturing (‘Fucking shoes you’re wearing. What are they? Designer?’) is at once endearing, pathetic and very, very funny.

The mirror is no accident. He’s looking at us, looking at him, looking at ourselves.     

Telephone Tough Guy

S4, E9 ‘Whoever Did This’

The Sopranos season 4 episode 9

While Ralph Cifaretto is probably most widely remembered as a sort-of gangster Loki – a mirth-wracked trickster with a penchant for mayhem – most of his misdeeds were so loathsome that even the wider mafia disapproved: cheating on his grieving partner, beating a young pregnant girl to death, burning a horse alive (come on, of course that was him). Still, he did make us laugh, though, didn’t he?

No more so than when he pranked Paulie’s dopey-yet-adorable old mother in her nursing home (‘It’s a retirement community!’), announcing himself as Detective Mike Hunt, Beaver Falls, from the Pennsylvania police department. Not only did Ralph claim that Paulie had been caught pleasuring a cub scout in a public bathroom, but also that a small rodent had been discovered in Paulie’s rectal passage. ‘A gerbil, ma’am’.

Ralph laughed his head off.

Tony later removed it.  

Ad – content continues below

A Truth Injection

S4, E10 ‘The Strong, Silent Type’

The Sopranos season 4 episode 10

Drug interventions are worthy and solemn rituals – they certainly aren’t supposed to be funny – but there’s something delicious about a room full of self-involved sociopaths with no impulse control and an insatiable appetite for pleasure assembling to pass judgement on Christopher essentially for having no impulse control and an insatiable appetite for pleasure. Christopher is at least self-aware enough to lobby this back in the faces of his supposed rescuers, pointing out that Silvio likes to sample his sex-workers; that Paulie’s hot-head almost dragged the Newark family into war with the Russian mob, and that Tony’s epicurean compulsions will probably kill him more quickly than Christopher’s drugs.

From the moment a bewildered Christopher emerges from his bedroom to find both families – blood and work – camped out in his living room, the laughs just keep coming, all the way through to the (inevitable) explosion of violence at the scene’s climax.

Christopher instantly recognises the host of the intervention, Dominic Paladino, as ‘the guy who broke into Stew Leonards that time and stole all those pork loins.’

‘Yes,’ replies a sheepish Dominic. ‘But… that’s not why I’m here today.’  

Especial mirth-based mentions must go to Silvio and Paulie (the latter’s reaction to Christopher’s narcotic-related manhood problems is priceless), and their refusal to play along with the ‘care-frontation’. 

‘When I came to open up one morning, there you were with your head half in the toilet. Your hair was in the toilet water. Disgusting,’ says Silvio, reading awkwardly from what is possibly the most unnecessary aide de memoire ever written.

Ad – content continues below

Leave it to Paulie to lay the smackdown on this particular brand of ‘California bullshit’: ‘I don’t write nothing down,’ he says, ‘so I’ll keep this short and sweet. You’re weak. You’re out of control. And you’re becoming an embarrassment to yourself and everybody else.’

Drugs are bad. Mmmkay?

Dead Good Food

S5, E7 ‘In Camelot’

The Sopranos season 5 episode 7 Uncle Junior

When Junior realises he can get respite from his house arrest through attending family funerals he starts to exaggerate and exploit ever more spurious links to get him out of the house for a few hours. While all around him are wracked with grief, his is the only face with a smile on it, enjoying the change of scenery, enjoying the food, wondering why everyone has to be so maudlin.

In a darkly funny scene he happily extols the virtues of the spread while attending the wake of a teenage boy. ‘Chicken’s nice and spicy, huh?’ he beams at a fellow mourner.

A Grave Error

S5, E9 ‘Unidentified Black Males’

The Sopranos season 5 episode 9

When Tony agrees to pick up the tab for the headstone of a New York soldier who was slain, unbeknownst to him, by his own cousin, his men manage to add insult to injury.

We see the headstone. At the graveside. During the funeral service. And it says:

Ad – content continues below


‘Peeps?’ spits Tony. ‘It’s a fuckin’ nickname! His family name is Pepperelli!’

Silvio hunkers down into full middle-management mode. ‘They’re gonna re-do it. Fuckin’ J.C. He’s dyslexic.’

 ‘What’s that got to do with it?’ asks an incredulous Tony. 

You could fill a book with The Sopranos’ funniest moments – Paulie’s rant about shoelaces, Bobby B botching a publicity shooting, Silvio’s poker-table tantrum, Little Carmine’s malapropisms, to name but a handful – so by necessity we’ve had to leave a lot out. What are some of yours?