How Christopher Went From Dreamer To Tragedy Case On ‘The Sopranos’

Over the course of The Sopranos run (which can be streamed in full on HBO Now), Christopher Moltisanti went from an irresponsible hijacker with dreams of playing himself in a movie to the Capo of a crew and a legitimate movie producer. The son of Dickie Moltisanti (a man Tony Soprano considered to be his mentor), Christopher was brought up among Tony’s crew, and groomed from the start to eventually be brought into the fold. Here’s a look at how Christopher managed to change over the years, as well as the unfortunate ways in which he seemed to stay the same.

“We have to stick together. Why be in a crew? Why be a gangster?”

When he’s first introduced, he’s an irresponsible kid who hijacks trucks and snorts meth with his buddy Brendan Filone. One of his earliest moments in the show involves him giving Tony’s daughter, Meadow, crystal meth, which she insists is a study aid.

Although his bad decisions run rampant, he looks for some kind of recognition to give his life purpose. Despite the onset of depression, he tries to write a screenplay. Christopher, at least in his own mind, is a struggling artist merely moonlighting as a gangster, and the lure of fame seems readily attainable. He also takes out his frustration by digging up the body of his first murder victim and shooting a pastry clerk in the foot after he’d ignored his order. Because, despite his artistic dalliances, he is a criminal raised by criminals.

Christopher suddenly feels vindicated by the end of the first season after seeing his name in print along with several other suspected associates of the North Jersey mafia. This allows him to reinvest himself in his identity as a wiseguy and a member of Tony’s crew, loving his life once more while believing that his life story is one that is worth telling.

“The next time a car disappears, make it two towns over. And I want a taste.”

At the start of the second season, Christopher has an office job, thanks to a fake stockbroker’s license. This introduces him to Sean Gismonte and Matt “Drinkwater” Bevilaqua, two ambitious wannabe criminals who Christopher takes under his wing, likely seeing a bit of himself in them.

Of course, he still dreams of making movies, and even ends up hanging on a movie set with Jon Favreau (playing himself) by way of his cousin’s girlfriend, who works as his assistant. But while he’s initially overwhelmed with excitement, he winds up feeling used when a rather sensitive story gets folded into a movie script.

Back in the less glamorous world of shady dealings, Tony notices his absence and gives his protege a choice… chase “whatever it is out there” that’s calling him, or be with him and his crew. Insisting he take the 10 minutes to think it over, it’s the first ultimatum given to him by Tony, and it’s the first time Tony shows doubt in Christopher’s commitment to him.

With the movie business out of his system (for now), his other recurring distraction, his drug habit, also comes up in a heated exchange between him and Adriana (his girlfriend, as played by Drea de Matteo).

A misunderstood conversation with Adriana’s uncle, Richie Aprile, prompts Sean and Matt to try and assassinate Christopher. He makes it out alive, but while on life support at the hospital after being clinically dead for 2 minutes, Christopher believes he sees a vision of hell.

Despite this brush with death, Christopher stays loyal to Tony after coming to him, but stays mostly on the sidelines for the rest of the season.

“The life is good enough for me, but not Little Lord F*ckpants?”

His loyalty pays off early in the third season, as Christopher finally gets made, securing a life-long ambition. Unfortunately, it doesn’t take long before things start to unravel and he screws up in the betting parlor, causing Paulie, his Capo, to tell him that “he’s not running a school” there.

In order to get the cash he needs to pay Paulie, he enlists the help of Dino Zerilli and Jackie Aprile, Jr., to commit a robbery. A move that raises Tony’s hackles because he had, years before, promised Jackie Aprile, Sr., that he would look out for his son.

“Oh, but it’s alright for me,” Christopher says with resentment, sparking Tony to explain that it’s because Jackie, Jr., isn’t “like him… like us,” before telling him he loves him.

Of course, Tony isn’t as perceptive as he thinks, and when a card game where Christopher is at gets robbed and he makes Jackie as one of the thieves, he throws Tony’s words back in his face, accusing him of being a hypocrite and then adding “I LOVED you.”

Christopher is told that while he may not love Tony, he will respect him, and as season three draws to its somber conclusion, he attempts to apologize to Tony, who simply shrugs him off.

“First thing I’m gonna do, get wings in my hair.”

Despite the still strained relationship, Christopher is given the identity of the man who he’s told killed his father years earlier, thus further indebting him to Tony.

As a result, Tony begins placing more and more trust in Christopher. He makes him acting Capo of Paulie’s crew, reveals his intention to give orders through him, and makes it clear that he is the future of the Soprano family. Christopher, meanwhile, relapses further into his drug habit.

He hits bottom after beating up Adriana, which prompts her and Carmela to hold a formal intervention, which inevitably erupts in violence. Afterward, in the hospital, Tony confronts him and berates him for being high when he was told he would bring the family into the 21st century. Christopher breaks down and promises to clean up his act.

“Alls I know is, I used to be the number one cousin. Now I’m being eased aside.”

Initially committed to sobriety at the start of season five, Christopher eventually questions his role in the family after the influx of new people (including Tony Blundetto) and falls into a drug and booze-fueled downward spiral when he hears a rumor about Tony and Adriana. The culmination comes on a dirt road with Tony holding a gun to Christopher’s head, imploring him to accept that he is telling him the truth. Ultimately, it’s Blundetto who steps in and provides a solution that convinces Christopher that there was no wrongdoing.

Later, after Adriana confesses that she’s been working as an FBI informant for years, he erupts with violence before collapsing while screaming, “What are we going to do!?”

As Adriana gets the call from Tony telling her of Christopher’s suicide attempt, followed by the long, scenic drive, it soon becomes heartbreakingly clear the decision that Christopher had made.

“Building blocks. Home, family…”

Starting off the first part of the sixth season, Christopher’s life looked to be in order once again. He’d moved on romantically, maintained his sobriety, and even began revisiting his filmmaking aspirations, as he and “Little” Carmine Lupertazzi travel to Los Angeles to try and lure Ben Kingsley into starring in their movie Cleaver. 

Unfortunately, his sobriety is short-lived, this time prompted by Tony after they stumble across a robbery that nets them a trunk full of wine. Before long, he’s shooting up in his car just seconds after preaching the value of an NA meeting.

It’s at a meeting that Christopher meets Julianna Skiff, a realtor who’d nearly had an affair with Tony earlier in the season. Before long, the two relapse together, accelerating a downward spiral Christopher had already set in motion (again). After keeping the relationship secret from Tony, fearing his potential reaction, Christopher comes clean by the midseason finale.

“Watching that scotch drip out of his fat f*cking mouth.”

After years of talking about his love for movies, back when “that candy and carpet smell” at Blockbuster was a relevant reference to make, Christopher finally gets his name on the silver screen, thanks to his low-budget mob/horror movie Cleaver. While it’s arguably Christopher’s high point, it’s his depiction of Tony in the movie-within-the show, that severs whats left of Tony’s attachment to him.

Christopher, however, has pulled away from the world entirely. He feels alienated by his sobriety, rightfully so, given how often he’s ostracized for it, and retreats into meetings with his sponsor. When he relapses again (this is Christopher, after all), his drunken, rambling musings cause him to get laughed out of the Bada Bing.

Ultimately, after a meeting with Phil Leotardo in New York, Christopher rambles on the way back about stopping to smell the roses, his car’s lackluster stereo, and its inability to properly play The Departed soundtrack. His carelessness causes them to wreck. After years of disappointments, tantrums, and last chances, Tony stops his call to 911 just long enough to suffocate the last bit of life out of him, ending one of the saddest stories in the history of The Sopranos.