The Class of 1999: 'The Sopranos'

The best dramatic television program ever produced debuted 25 years ago today.

1999 was a historically-great year for film and dramatic narrative as a whole. I’m using my 2024 to look back at, reconsider, and honor these stories as they all celebrate their 25th anniversaries. Join me, won’t you?

The Sopranos - created by David Chase - January 10, 1999

In January of 1999, television introduced the world to a rotund sociopath and his family, and that colorful, insane group of men, women, and children changed all of our lives, forever.

I’m talking, about course, about Peter Griffin.

Sorry… did you think I was referring to someone else?

Oh, right. Tony Soprano. I guess my description could also apply to him, sure.

Ugh, fine, let’s talk about his show, then.

It is an unavoidable cliché to say that The Sopranos changed the way we watch television.

It’s not as though premium cable networks had never before produced original content; HBO started making its own programming way back in the early ‘80s, and by the time The Sopranos aired, some of their shows, like Oz and The Larry Sanders Show, had already found acclaimed. It’s hard to know how or why, exactly, The Sopranos broke through into mainstream consciousness on such a massive level, thereby putting “prestige television” on the map. It could just be a case of cream rising to the top, except we know that’s not really how things work - if it was, Freaks and Geeks, which debuted that fall, wouldn’t have been cancelled after a single season. It could have something to do with the next evolution of technology - TiVos and other DVRs were introduced into the market in 1999 and streaming video was just a few years away, both of which made the once-inescapable task of sitting through commercials seem much more irritating… although I’m not sure it’s that, either, because people were still sitting through commercials for shows like Friends and, also later in 1999, The West Wing.

What I think actually happened was that The Sopranos was half of a killer one-two punch from HBO - Sex and the City debuted seven months prior, almost to the day. Both shows quickly entered the mainstream lexicon, and suddenly HBO had two hit programs, which potentially appealed to very different audiences. The network abruptly became central to all water cooler conversations and many think pieces about the “new golden age of television.”

Regardless of why it happened, two things are true.

The first is indisputable: The Sopranos paved the way for every great (premium OR basic) cable (or streaming!) drama since, from Six Feet Under and The Wire to Dexter and Breaking Bad to The Walking Dead and Game of Thrones.

The second is disputable, assuming you’re looking to pick a fight with me: The Sopranos is, from start to finish, an the best dramatic television program ever produced. It’s been off the air for nearly seventeen years - nearly twice as long as it actually ran - and everyone STILL talks about it, like, ALL THE TIME.

And that, I think, is a case of the cream rising to the top. The Sopranos remains an unrivaled masterpiece.

But what makes it so? On paper, large swaths of The Sopranos are boilerplate mob clichés we’ve seen a million times before and since. On a macro level, the story has more or the less the same rise-and-fall trajectory of most stories where the protagonist is a criminal. On a micro level, its episodes all follow the standard structure of serialized television, where there’s an A-story (Tony has a mob conflict) and a B-story (Tony is working something out in therapy) and maybe even a C-story (usually involving Tony’s biological family), which are connected thematically, if not literally.

The Sopranos wasn’t even the most unique mafia story of the year it came out: Analyze This, a comedy with the completely identical premise of a mobster suffering from panic attacks going to see a psychiatrist, opened just a couple of months after The Sopranos debuted. Directed by Harold Ramis and starring Billy Crystal and Robert De Niro, the now-mostly-forgotten Analyze This seemed like the far safer bet at the time, too.

So what makes The Sopranos a cultural touchstone? How did David Chase and his crackerjack team of great writers and directors succeed where so many others have failed?

Part of it almost certainly is the fact that it was a serialized television show and not a single-shot movie. Never mind that a movie wouldn’t allow for getting to know Tony so well - it wouldn’t have allowed for getting to know the members of Tony’s two families so well (and if you don’t believe me, try watching The Many Saints of Newark sometime). The Sopranos may not be an epic in terms of its physical scope, the way movies like Lawrence of Arabia are, but it is certainly a character epic, which is what having 86 hours to tell your story allows you to do.

Which calls attention to the element of The Sopranos that was unique right from its first airing: mob stories had, up until this point, generally been confined to the movies. Oh, sure, there were television shows about the heroes fighting the mob, but there wasn’t really ever a show where a gangster was the protagonist. The closest thing to The Sopranos prior was probably Wise Guy, which ended ten years earlier, and was still, technically, about law enforcement (the protagonist was undercover).

And part of it is the fact that The Sopranos was deeply funny in a way that mafia stories didn’t tend to be. Mob comedies were generally very broad (like Mickey Blue Eyes, which also came out in 1999 and featured Vincet Pastore), and the humor in mob dramas usually derived from characters who were either colorful (Joe Pesci in Goodfellas) or stupid (Luca Brasi in The Godfather). The Sopranos had colorful and stupid characters, to be sure, but it also had a slightly-detached wit that those other titles lacked (the closest equivalent might be Jonathan Demme’s Married to the Mob, although that’s still comparatively zany). In other words, everyone in Goodfellas knows Joe Pesci is funny, and part of the humor from Luca Brasi in The Godfather comes from Vito Corleone’s obvious discomfort over talking to such an idiot, but there are constant laughs in The Sopranos which aren’t cartoonish AND which would not actually be funny to any of the characters onscreen: Tony misquoting Melfi (“Captain Antibes”), a mostly-naked stripper reacting to a gangster’s death by sincerely vowing “I’ll never forget where I was this day,” the way Tony’s mother, Livia (Nancy Marchand), won’t admit that she wants a box of a macaroons, etc. What The Sopranos lacked in originality of plot it made up for with uniqueness of tone.

But I still think that’s only part of the picture.

I think the biggest part of what makes The Sopranos stand apart from the crowd may be because the story works on multiple levels.

One way to read The Sopranos is as a story about change - or, rather, failure to change. At the end of Analyze This, the psychiatrist convinces the mob boss to quit the mafia; at the end of The Sopranos, the psychiatrist, Dr. Jennifer Melfi (Lorraine Bracco), throws the mob boss, Tony Soprano (the magnificent James Gandolfini), out of therapy because he never changes (“We’re making progress! It’s been seven years!!” Tony protests without a hint of irony). Viewers who complain that the series’ divisive finale failed to provide resolution miss this aspect of the show’s thematics. By the conclusion of the story, all of Tony’s closest friends, save for one, have been killed or imprisoned. It doesn’t matter if Tony is whacked today or arrested tomorrow or flipped next month; because he either will not or cannot change, it is all but inevitable that he will meet one of these tragic ends.

The entire Soprano family, in fact, is doomed to be forever trapped in the endless destructive cycle of criminal life: Carmella (Edie Falco, stupendous) will never be able to to leave Tony, Meadow (Jamie-Lynn Sigler) is engaged to the son of Tony’s gangster associate, and A.J. (Robert Iler) is working a “legitimate” job for yet another mobster in a job Tony got him (and which immediately gifted him a BMW). We have seen, over the course of 86 episodes, that the odds of these people going on to have happy and healthy lives is not high.

The Soprano family’s fear of change is prevalent right from the pilot episode. Tony bellyaches about “the good old days” frequently, and his panic attacks are precipitated by “feelings of loss” (Dr. Melfi’s words), as embodied by seeing the baby ducklings he loves so much fly away from his pool, never to return. Tony’s mother, Livia (Nancy Marchand, A+++++), won’t get over the death of Tony’s father, won’t abandon the faux-genteel standards of her past (e.g., not answering the phone after dark), won’t accept that she’s getting older and needs help, and won’t allow Tony to upgrade her music collection to the latest format (which was CDs at the time - today it would probably be Spotify). Carmella won’t accept that Meadow is growing up, and Meadow punishes Carmella by refusing to engage in their tradition of taking tea at the Plaza.

The theme of desperately holding onto things as they are continues throughout the first season (and the show), which also gradually reveals why these characters cling to that which is killing them. When trying to comfort his dying friend, Tony calls the man by his full Italian name, Giacomo, not “Jackie,” as he usually does; every Italian-American character is obsessed with their ancestors’ contributions to history and culture, as if it was their very own achievement; “We gotta stick together,” Christophuh (Michael Imperioli) insists at one point. “Otherwise why be in a crew? Why be a gangster?” (so much for sticking together: Tony eventually murders Christopher). There are reassurances in “the way things are” (or, perhaps more appropriately, “the devil you know”) - never mind that those reassurances will likely be the death of you.

Not-quite-paradoxically, it is with the promise of change that Tony Soprano seduces the viewer (and, in a way, Dr. Melfi). Sure, Tony is a charismatic, funny (assuming you appreciate sarcasm), and smart (if uneducated) - but he’s also a homicidal, sociopathic, philandering thief. And yet we often quite like him. That all grows out of his sessions with Dr. Melfi.

On a practical level, those meetings allow - nay, necessitate - a deep-dive into his psyche, which often makes him more vulnerable and self-aware than these kinds of characters tend to be.

On a less literal level, being “in treatment” signals that someone is trying to better themselves. We feel empathy for Tony not just because we know his pain, but because we feel, on some level, that he is working desperately not to be the kind of guy who cheats, steals, and murders.

But we, not unlike Tony and Dr. Melfi, are lying to ourselves. The Soprano family will never change. What is the very last thing we hear - the absolute final words uttered - in the series finale?

“Don’t stop.”

Another way one could read The Sopranos, however, is as a mafia story about mafia stories… or, more specifically, a mafia story about our cultural relationship to mafia stories.

Dr. Melfi and her inner circle aside, the characters on The Sopranos may not the most well-educated bunch - but they’re certainly media-literate. The characters reference The Godfather and other famous mob movies incessantly, to such a degree that in conversation, one need only say “Part I” or “Part II” and another will completely understand what they mean, as if Coppola’s films are the Gospels from The Bible. In an early episode, Tony and the boys all get DVD players for the first time, and immediately start asking questions about its alleged superiority to laser disc. Carmella and Father Phil love watching and discussing classic films. Maybe most humorously, Christopher is OBSESSED with breaking into the movie business (he eventually writes a movie described as “Saw meets The Godfather Part II”). In the second season, there’s an entire episode, “D-Girl,” in which Jon Favreau plays himself; in the first season, there’s a quick cameo by Martin Scorsese cutting the line at a nightclub - Christopher shouts at him “Kundun! I liked it!” Which is hilarious, because it both calls out critics who undervalued Scorsese’s Dalai Lama biopic and shows how desperately Christopher wants to be perceived as hip (he doesn’t name-drop a super-popular Scorsese movie like Raging Bull). It’s an amazing joke.

It’s also a reality-bending joke which highlights The Sopranos’ postmodernist sensibilities - for if in the world of The Sopranos Michael Imperioli is Christopher Moltisanti, and he does not know Martin Scorsese, than who the heck played Spider in Goodfellas?

The cast of The Sopranos is, in fact, overflowing with recognizable faces from popular Scorsese mob movies: Bracco (also Goodfellas), Pastore (also also Goodfellas), Tony Sirico (still Goodfellas), Frank Vincent (Goodfellas AND Casino), and David Proval (Mean Streets), to name just a few (and that’s to say nothing of the fact that Dominic Chianese was in The Godfather Part II).

These actors - like the basic plot developments - were largely pre-tested successes in the world of mafia movies (like, have you ever seen Tony Sirico or Frank Vincent play anything BUT a gangster?). Chase knew that with the exception of Bracco, if viewers recognized these actors, it would be from playing exactly the same kinds of characters they were playing here. Even Gandolfini’s most well-known roles at that point, in movies like Get Shorty and True Romance, were mobsters.

Chase calls draws attention to these connections because he wants the audience to think about them as they watch The Sopranos unfold. And he does that to link up the reality that Tony Soprano won’t change with the reality that WE AS A SOCIETY won’t change - we keep romanticizing these goddamned maniacs.

Or, maybe more accurately, we keep misunderstanding the meaning of narratives about these goddamn maniacs. As Devin Faraci so beautifully put it in his review of Killers of the Flower Moon last year:

“Over the decades Scorsese has given us many stories of venal, vile men, violent avatars of the true nature of American capitalism. Again and again he has told stories about these men and their rises and their falls, and again and again audiences have simply not gotten it. See, he’s too good, and what that means is that he imbues these stories with a rollicking, rousing sensibility that can confuse people who think that Goodfellas is a guide to life or that The Wolf of Wall Street is a celebration.

“Of course this is why we love him - he doesn’t just show us sin, he shows us the appeal of it, the joy of it. He lets us partake in it, to feel the rush of knuckles on a cheek bone or a night out with a mentally unbalanced but incredibly hot mistress. In these movies about bad men he makes us complicit in it and then he pulls the rug out, letting everything fall and revealing these creeps with whom we have identified for an hour and a half as the shallow pieces of shit they are. It’s brilliant, but for some reason a not small segment of the audience just can’t get past the rousing part. It’s too good, they get stuck there.”

Faraci’s larger point was about the way that Scorsese has recently shifted his approach, in films like Flower Moon and The Irishman, to ostensibly drain the movies of fun so that less-astute viewers stop getting confused as to the point he’s trying to make. But Chase’s more cynical point, made two decades prior to The Irishman, is that a large segment of the audience will never properly interpret these stories. We, like Tony Soprano, have seen endless examples of this schtick - often with the same exact players! - and yet we keep coming back for more. We are fascinated by Vito Corleone and Tony Montana and, of course, Tony Soprano. We slap their faces on t-shirts and dorm room posters and empower them to be cultural icons and write puff pieces about how cool they are.

And there’s no real solution, because the very elements that make them fascinating characters are the same elements that make them decidedly not cool AND the same elements that make them seem cool. It’s a power fantasy - to take away Tony’s proclivity for violence and betrayal would be like taking away Superman’s ability to fly and stop bullets. It’s part and parcel.

“Don’t stop” isn’t just Tony’s mantra - it’s ours. The Sopranos don’t want to stop - and we don’t want the Sopranos to stop - because we don’t want The Sopranos to stop. As a wise man once said: