10 Sopranos Bittersweet Moments

10 Sentimental, Beautiful, and Bittersweet Moments on The Sopranos

When someone asks me to describe The Sopranos, the best way I know how is to quote A.J.’s principal, Robert Wegler: “Somehow horrifically funny, though tragic.” Along with its fair share of ziti, f**kin’, and f**kin’ ziti, The Sopranos is at times quite heartwarming, tinged with nostalgia and bittersweet moments of reckoning. While they’re not the bloodiest, the most tragic, or quite as nerve-wracking as others, here are 10 bittersweet moments on The Sopranos that give me all the feels.

Meadow Soprano is eating dinner with her father, Tony Soprano, at a nice restaurant on their college tour.
The Sopranos, Season 1, Episode 5, "College"

Season 1, Episode 5 - College

First, I know I’m not alone in stating that College is one of my favorite Sopranos episodes. For the purposes of this post, I turn to Tony and Meadow at dinner. Everything from Tony telling Meadow how proud he was of her academics, to discussing the Potsdam Conference (“Pots-damned if I know now!”) to Meadow confiding in Tony, it was a truly beautiful moment. 

Happy Families - Not the Season 5 Kind

Season 1, Episode 13 - I Dream of Jeannie Cusamano

Tony, Carmela, Meadow, and A.J. are eating at Vesuvio while Adriana, Christopher, Paulie, and Sil are in the same dining room, just at separate tables.
S.1, E.13, "I Dream of Jeannie Cusamano"

Next, we get to the season one finale. Facia Bruta!  In the episode’s final scene, Tony, Carm, Meadow, and A.J. took shelter at Vesuvio after a storm caught them on their way to Aunt Patty’s. I feel like their taking refuge at Vesuvio was symbolic of the family seeking sanctuary from the chaos of the outside world. In addition to the family of four, Paulie and Sil had their own table, while Adriana and Christopher sat together at the bar. Those lovesick pygmies, huh?

"I'd like to propose a toast. To my family. Someday soon, you're gonna have families of your own. And if you're lucky, you'll remember the little moments...like this...that were good."

You Can't Put Your Arms Round a Memory

Season 2, Episode 11 - House Arrest

The boss and capos of the DiMeo crew are standing outside of Satriales while Big Pussy Bonpensiero walks inside.
The Sopranos, Season 2, Episode 11, "House Arrest"

Next up, we’re toward the end of season two, but what’s so special about the guys standing outside of Satriale’s? Well, for the purposes of this post, I’ll mention a few things:

  • The song “You Can’t Put Your Arms Around a Memory” by Johnny Thunders is PEAK sentimental Sopranos for me.
  • Big Pussy Bonpensiero turning around and walking back inside…talk about some wicked foreshadowing, huh? 
  • Agent Harris and Tony shooting the sh*it about local sports and trivial things on the street always amuses and intrigues me. Though we don’t know it yet, Agent Harris remains present throughout the entire series and eventually becomes an ally of sorts.

Season 2, Episode 13 - "Fun House"

tony soprano is lighting a cigar in the middle of his house during meadow's graduation party.
a close up of tony soprano's face as he blows out cigar smoke in his house.

Likewise, when it comes to bittersweet moments on The Sopranos, the season two finale, “Fun House,” takes it to a whole new level. There’s the car ride with “Free Falling,” the struggle to push Big Pussy’s body into the ocean, followed by Meadow’s graduation, where we all felt that obvious absence. In the final seconds, with Thru & Thru accompanied by the majestic ocean waves, the moment is truly indescribable.

The waves crashing against the shore in The Sopranos season two finale.
The Sopranos, Season 2, Episode 13, "Fun House"
"Well, that's the difference between Pussy and the others. Him you loved."

Pie-O-My - Just My Rifle, My Pony, and Me

Tony Soprano is sitting with Pie-O-My at night in the stable as Pie-O-My lies down to rest and recover.
The Sopranos, Season 4, Episode 5, "Pie-O-My"

Season 4, Episode 5 - "Pie-O-My"

Following season two, I turn to the middle of season four and “Pie-O-My.” As you likely know, Pie-O-My turned out to play quite a significant role in DiMeo family affairs. What always gets me, though, is when Tony goes to see Pie-O-My at the stables late at night to make sure she gets the medical care she needs. Not only that, he sat with and comforted Pie-Oh-My after her procedure (her goat friend was there, too). There was something very special about them together in the quiet stable, listening to the rain and, perhaps, exhaling for the first time in awhile. 

A Summer of Cold Cuts

Season 5, Episode 10 "Cold Cuts"

Johnny Cakes - You Gotta Grow Up, A.J.

Tony Soprano touching A.J.'s face while A.J's crying outside.
Season 6, Episode 8, "Johnny Cakes"

Season 6, Episode 8 - "Johnny Cakes"

After Pie-O-My, I take a big leap to season six, episode eight, “Johnny Cakes.” There’s a lot to say about the actual Johnny Cakes, but I’ll get to that in a separate post. For now, I turn to the moment Tony tells A.J. it’s time to grow up. I’m far from A.J.’s biggest fan, but this scene always gets me choked up.

While softly stroking A.J.’s cheek and wiping his tears, Tony tells him it’s time to grow up. This interaction followed A.J.’s impulsive trip to find Uncle Jun and get revenge for Uncle Jun shooting Tony earlier that season. Sure enough, the only thing A.J. did was freak out and drop the knife, but it was very symbolic of A.J’s lack of identity and feeling of being lost on this journey of life. I think many of us can relate to that in one way or another.

The Ride - Tony twirls around with Nica

janice soprano and bobby bacala's baby, Nica, is walking towards a ride at the Feast of St. Elzéar.
The Sopranos, Season 6, Episode 9, "The Ride"

Season 6, Episode 9 - "The Ride"

While you may not like the idea of Janice and Bobby together, it’s hard to deny they made one cute kid. Domenica (“Nica”) was quite the adorable baby, but what made this part truly unforgettable for me was when Tony picked Nica up and twirled her around in the air. Everything about that moment depicted such innocence and joy that you almost forgot about the piano (got that one from Carmela) hanging over Tony’s head. 

The Ride - You Want Some Cookies? Paulie & Nucci

Paulie Walnuts is sitting on the sofa and Nucci Gualtieri, Paulie's mother, is about to sit down with him to watch television.
The Sopranos, Season 6, Episode 9, "The Ride"

Season 6, Episode 9 - "The Ride"

In addition to Nica and Tony, Paulie Walnuts and his Ma, Nucci Gualtieri, have a particularly bittersweet moment in The Ride. For those of you about to shout “That’s his aunt!” never you mind. For all intents and purposes, Nucci is Paulie’s ma. Paulie was devastated earlier that season in The Fleshy Part of the Thigh when he found out that his aunt Dottie was actually his mother, and that Nucci was his aunt that raised him as her son. Paulie took this news pretty horribly, but he at least made (partial) amends by sitting with Nucci here and watching television. 

This Magic (and Bittersweet) 6(B) Moment

Bobby Baccalieri holding his daughter Nica in Soprano Home Movies
Season 6, Episode 13, "Soprano Home Movies"

Season 6, Episode 13 - "Soprano Home Movies"

Not long after The Ride, we arrive at season 6(b). That final scene in “Soprano Home Movies” showing Bobby and Nica standing by the lake was such a bittersweet moment on The Sopranos, as we’d soon meet the darkness that was just around the corner. This scene reminds me in some ways of Tony and Nica twirling around in the Ride, though we’re more acutely aware here of the piano over everyone’s head.

Stage 5 - Little Carmine Tells Tony What It's All About

Little Carmine is talking to Tony Soprano over lunch at a golf club and telling him that what's important is to be happy.
The Sopranos, S.6, E.14, "Stage 5"

Season 6, Episode 14 - "Stage 5"

Surprisingly, it was the very character so many underestimated who in the end played the long game well. I think part of playing the long game was knowing not to play the long game, if that makes sense. As Little Carmine explained to Tony, “It wasn’t about being boss. It was about being happy.” At the end of the day, what’s so good about being the “mother-f**kin-f**kin-one that calls the shots” if you’re all alone making calls.

Remember When - Country Road, Take Me Home...

the patients at junior's nursing home are singing a song together.
The Sopranos, S.6, E.15, "Remember When"

Despite having never lived in a rural area or having any connection to West Virginia, “Take Me Home Country Roads” causes these deep feelings of sentimentality. Though oddly enough, the song’s authors were inspired to write it while driving through Montgomery County, Maryland. Sure enough, Montgomery County, Maryland is the county in which I was born. You guessed it: Quasimodo really did predict all this

Wrapping It Up

Big Pussy Bonpensiero is talking to Jackie Aprile Sr and Tony Soprano down on the boardwalk.
"I always wanted a house by the ocean. Maybe in another life."

In sum, much of what makes The Sopranos so powerful is its ability to resonate with people from all walks of life. The moments on the show that we find the most bittersweet could be a result of our particular experiences and the lens through which we view the world. This list was merely my own. What about you? What were some of the most bittersweet moments on The Sopranos for you? To take it to the present day, are you looking forward to seeing The Many Saints of Newark? Sign up below to subscribe to Sopranos Blueprint and follow me on social media. 

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