William “Bill the Butcher” Cutting (Daniel Day Lewis), “Gangs of New York”
Using 19th century New York City gang leader William Poole as a launching pad, Scorsese brings to the screen his most magnetic and monstrous villain with Bill “the Butcher” Cutting. Played with ruthless calculation and conniving intensity by Daniel Day Lewis, Cutting is a towering screen presence — you simply can’t take your eyes off him. Based on Herbert Asbury’s 1927 non-fiction book, “Gangs of New York” centers on Leonardo DiCaprio’s Amsterdam Vallon, a young Irish immigrant who loses his father to Cutting’s reign of terror and plots his revenge against him two decades later. Bringing the adult Vallon unknowingly under his wing, Cutting proves dangerous and charismatic all at once. Lewis, inhabiting the role with a blazing fire in his eyes that is impossible to put out, is always seconds from snapping, making Cutting a spontaneous force of destruction. Scorsese has always loved power-hungry madmen (and actors who can give a stirring monologue), and Cutting is one of the director’s best.
Rupert Pupkin (Robert de Niro), “The King of Comedy”
In 1982, the defining films in Martin Scorsese’s body of work were violent, gritty dramas in the vein of “Mean Streets” and “Taxi Driver,” and so many viewers weren’t sure how to handle the dark interior exploration of “The King of Comedy.” As Jerry Langford (Jerry Lewis) tells aspiring late-night host Rupert Pupkin (Robert De Niro), “You’ve got to start at the bottom,” and start at the bottom he does. Rupert hosts a talk show with an audience of none in his mother’s basement with dreams of making it into show business for real some day. He does this in the only way that seems logical: He stalks his TV idol, Jerry Langford. This film is the blackest of comedies, and De Niro is the textbook definition of pathetic as the naive, celebrity-worshipping Pupkin. Decades later, Pupkin’s ruthless obsession with fame and celebrity still hits a raw, topical nerve.
Travis Bickle (Robert De Niro), “Taxi Driver”
The anarchistic and borderline psychotic Travis Bickle in “Taxi Driver” is one of the most iconic creations of both Scorsese and the star who brought him to life, Robert De Niro. As Bickle spends his time cruising through the shadiest, seediest parts of 1970’s New York City as a late night cab driver, he’s exposed to the dark underbelly of urban grit. One of Scorsese’s quintessential anti-heroes, Bickle finds himself both tempted by the dark side and utterly repulsed by it, succumbing to chaos and disorder while trying his best to rid it from his city after he befriends a 12-year-old prostitute (Jodie Foster). While the version of New York it portrays is no more, De Niro’s performance as Travis Bickle is cinematically timeless.
Alice Hyatt (Ellen Burstyn), “Alice Doesn’t Live Here Anymore”
Just a year after Scorsese released “Mean Streets,” he took a startling detour in tone and storytelling for “Alice Doesn’t Live Here Anymore,” a scrappy feminist melodrama built on heartbreak, love and maternity. Mixing comedy and drama with a sensitive pathos, the director puts the emotional weight of the film on Ellen Burstyn’s shoulders, and she deservedly won the Oscar for Best Actress for creating a uniquely individual female screen protagonist. Alice is hot-headed, self-assured and driven to be the best mother she can, yet she still finds herself under love’s spell time and time again. She’s by no means weak, she’s just in touch with a vulnerably feminine side of herself that puts heart over reason, often leaving her in painful relationships she can’t seem to get out of. Scorsese is most famous for his abrasive men, which alone makes the affectionate Alice the rare anomaly in his filmography.
Tommy DeVito (Joe Pesci), “Goodfellas”
Funny how? Funny like a clown? Although Scorsese pulled from real life to inspire his “Goodfellas,” the indelible Tommy DeVito stands apart as a man all his own, divorced from mythos (and, quite often, reality itself), crafted as one of the filmmaker’s most iconic offerings. Although the stuff that makes Tommy tick — a bit of a Napoleon complex, a desire to fit in, an inability to take a joke — is fairly obvious from the get-go, as the mob drama winds on, Tommy continually surprises the audience, the rest of the film’s characters and even himself with some of his off-kilter reactions and majorly wild outbursts. You think he’s funny?
Jake LaMotta (Robert De Niro), “Raging Bull”
“Raging Bull” is a dramatized account of the life and career of World Middleweight Champion boxer Jake LaMotta. LaMotta, also known as “The Bronx Bull,” was remembered as a “bully” in the ring for his sometimes sloppy and always ruthless fighting style, staying close and absorbing his opponent’s punches while delivering a constant beat down of his own. LaMotta’s style in the ring parallels his approach to life, absorbing constant hardships but always lashing out violently against those closest to him. In “Raging Bull,” LaMotta rages against his inner demons as his relationships suffer while his career keeps growing, leading to a heartbreaking final scene depicting an aging and overweight LaMotta trying to make it as a stand-up comic after his boxing career is over. The character makes for a brutal exploration of a fighter’s twisted psyche.
Ginger McKenna (Sharon Stone), “Casino”
Jesus, Ginger. Driven by forces beyond her control, like an insatiable desire for material gains and a tremendous thirst to be with her own child, Ginger is nearly incapable of making the correct decision. Although her love for Sam Rothstein (Robert De Niro, of course) costs her nearly everything — and turns her into one of cinema’s greatest villainesses in the process — there’s still a kernel of understanding bubbling just beneath the surface, hinting at far greater forces at work beyond just a love for big diamonds and bad men.
Fast Eddie Felson (Paul Newman), “The Color Of Money”
Two decades after he introduced cinephiles to Fast Eddie Felson in “The Hustler,” Paul Newman returned to a role that Scorsese would redefine for a new generation, fully taking advantage of the time jump to craft an emotionally reflective tale about legacy. A far cry from the cocky gambler we met in 1961, Felson is now a liquor salesman who is drawn back into a life of bets and pool sharks after he begins to mentor Tom Cruise’s hot-shot prodigy. Just as before, if not more so, the gambler’s spirit is rendered viscerally by Newman, who paints a complex picture of an imperfect and aging masculine ego, flawed by the same instincts that leave him raw and relatable. Scorsese’s mentor figures are often controlling, but here he turns Felson into an empathetic exception. Felson doesn’t just want to be remembered, he wants his name to mean something important to those he leaves behind. At age 61, the soul-searching Newman has never been better.
Frank Costello (Jack Nicholson), “The Departed”
Jack Nicholson gives one of his last great dramatic performances in “The Departed,” where he plays Irish mob boss Frank Costello. Costello keeps no secrets about his criminal empire; he’s become too powerful for even the police to bring down, and his bravado gives him a profound influence over those around him. In the film, Leonardo DiCaprio’s Billy is an NYPD cop who is tasked with going undercover in order to get close to Costello and dig up information the police can use to finally make an arrest. Nicholson flips back and forth between the persona of a cold-hearted mob boss and a twisted paternal figure, keeping Billy at his right hand to be his mentor while holding him under constant scrutiny as the potential “rat” in his operation. The duel sides of this criminal mastermind keep viewers perpetually guessing about what he’s really capable of, and what he will do next.