Widely regarded as a cinematic masterpiece and one of the greatest gangster films ever made, Martin Scorsese’s Goodfellas (1990) earned critical acclaim upon release, receiving six Academy Award nominations, with Joe Pesci winning Best Supporting Actor. Based on Nicholas Pileggi’s non-fiction book Wiseguy, the film was later selected for preservation in the U.S. National Film Registry for its cultural significance. It immerses viewers in the intoxicating and perilous world of organized crime through the true story of Henry Hill (Ray Liotta), tracing his journey from a wide-eyed teenager in 1950s Brooklyn, captivated by local Lucchese crime family associates, particularly the powerful capo Paulie Cicero (Paul Sorvino), choosing their path over a conventional life.
The narrative follows Henry’s ascent alongside the calculating James “Jimmy the Gent” Conway (Robert De Niro) and the pathologically violent Tommy DeVito (Pesci), vividly portraying the seductive glamour and brutal realities of their criminal enterprise. Goodfellas masterfully explores themes of loyalty, ambition, and the corrosive effects of violence, extending into Henry’s turbulent marriage to Karen (Lorraine Bracco), who becomes entangled in the lifestyle’s dangerous allure. The film charts the escalating stakes, paranoia, and inevitable betrayals inherent in their world, culminating in Henry’s eventual downfall and his fateful decision to break the mafia’s code of silence.
Henry’s Early Mob Career
In 1955, Henry Hill (Ray Liotta) came of age in a Brooklyn neighborhood teeming with Italian-American families. While his peers harbored dreams of becoming doctors or pilots, Henry was captivated by the neighborhood gangsters. These local mobsters frequented a cabstand operated by Tuddy Cicero (Frank DiLeo), the brother of Paulie Cicero, a powerful and reserved mob capo. When Henry landed a job at the cabstand, he was ecstatic. Henry’s parents initially appreciated their son’s apparent industriousness but changed their tune when a letter arrived revealing his prolonged absence from school.
When Henry confided in Tuddy about quitting, it triggered immediate action. The next morning, Tuddy and the mobsters intercepted the mailman, threatening him to redirect all school correspondence to the cabstand instead of Henry’s home. After that, no school letters ever reached the Hill residence. Henry quickly became entrenched in the mob’s operations, mastering various schemes from errands to arson. He chauffeured Tuddy, ran messages, and even torched buildings for insurance scams. Under Paulie’s quiet yet commanding presence, Henry’s role and income expanded, soon affording him luxuries his father never could.
Later, at a bar operated by Paulie, James “Jimmy” Conway (Robert De Niro) made his entrance—an Irish-American gangster already notorious for hijackings, even at just 29. Henry was instantly drawn to him. Unlike reluctant criminals, Jimmy relished the life. Whether it was cigarettes, booze, or razor blades, everyone lined up to help Jimmy because he paid generously and treated his crew well.
Henry quickly bonded with Jimmy and began working alongside the volatile Tommy DeVito. After being caught selling stolen cigarettes, Henry faced his first court appearance but was bailed out by his mob connections. Jimmy rewarded his silence with a wad of cash, reinforcing the lesson: “Never rat on your friends, and always keep your mouth shut”. By the early 1960s, Henry and Tommy expanded their operations to JFK Airport, collaborating with corrupt staff to intercept cargo shipments. Their biggest score involved untraceable cash sent to France, from which Henry claimed to have earned over USD 400,000.
Henry remained relatively grounded, unlike Tommy, who became frequently abusing power and exploiting his mob status. One example was his treatment of Sonny Bunz (Tony Darrow), the Bamboo Lounge owner. Tommy routinely ate and drank without paying, and when Sonny politely asked for payment, Tommy brutally beat him. Out of desperation, Sonny approached Paulie Cicero for help, offering him a partnership in exchange for protection. Though initially hesitant, Paulie agreed, leading to the eventual downfall of the Bamboo Lounge as it was drained financially and ultimately burned down for the insurance.
Marriage and Escalating Violence
Henry and Tommy’s bond extended beyond work, they often socialized together. One double date led Henry to meet Karen Friedman (Lorraine Bracco). Coming from a respectable Jewish family, Karen initially believed Henry worked in construction. When a neighbor tried to grope her, Henry retaliated with a vicious beating using the butt of a pistol, leaving the weapon in Karen’s hand as he walked away. The violent act startled and excited her. Karen found herself increasingly entangled in the allure and danger of Henry’s world. They eventually married in an elaborate wedding, filled with envelopes of cash from mobsters. Karen later admitted that, though she knew Henry wasn’t just a construction worker, she only fully understood the extent of his criminal lifestyle after they were already married.
Her perspective shifted when she joined the social circle of other gangsters’ wives. These gatherings evolved into therapeutic venting sessions about their complicated lives—some women had husbands serving prison sentences, others were raising children battling addiction, and many endured hardships unique to families entangled with the mafia. Whenever Karen voiced her concerns to Henry, he skillfully placated her, normalizing their extraordinary circumstances. Initially troubled by their situation, Karen gradually became desensitized to the dark underbelly of mafia life.
On June 11, 1970, a pivotal moment unfolded at Henry’s nightclub, The Suite. As the gang engaged in casual conversation, Tommy arrived with a female companion. Billy Batts (Frank Vincent), a member of the Gambino crime family whom Tommy hadn’t encountered in years, greeted him by mockingly referencing his past as a shoeshiner. The now-transformed Tommy perceived this as a grave insult. Billy stubbornly refused to apologize, dismissing his teasing as harmless banter.
Henry attempted to mediate the tension, mindful that Tommy was accompanied by a woman. However, later that evening, Tommy returned with Jimmy’s assistance. They viciously beat Billy, pistol-whipping him until he was unconscious. They hastily loaded the presumed-dead Billy into a car, making a detour to Tommy’s mother’s house for tools before proceeding to bury him in a desolate vacant lot. En route, they discovered Billy was still alive, prompting them to beat him to death with a shovel and tire iron.
For these hardened gangsters, murder had become disturbingly commonplace—triggered by either significant disputes or trivial matters, as in Billy’s case. One unspoken rule permeated their existence: gangster life demanded unwavering readiness to kill or be killed. This particular murder created extraordinary complications because Billy was an official member of the Gambino crime family. Attacking a made man without organizational approval violated their sacred code. Such violations inevitably carried fatal consequences.
When Paulie later questioned Henry about Billy’s whereabouts, Henry maintained his silence. Billy’s mysterious disappearance bewildered their circle, intensifying pressure on Paulie. He explicitly instructed Henry to report immediately any information regarding Billy’s location. Henry never disclosed anything to Paulie. Instead, troubling news emerged that their burial site had been sold for apartment development. They frantically rushed to exhume Billy’s remains. The overwhelming stench of the decomposed corpse caused Henry to vomit repeatedly.
Affairs, Prison, Drug Dealing
A night-dwelling gangster like Henry inevitably sought companionship beyond his marriage. After becoming involved with Janice Rossi (Gina Mastrogiacomo), a club entertainer, he purchased her an apartment for their rendezvous. Henry’s increasing absences raised Karen’s suspicions, leading her to track down Janice’s apartment and confront her. Unable to gain entry, Karen caused a scene, shouting insults and drawing attention from neighbors. Later, Karen confronted Henry at home, waking him by pointing a gun at his face and threatening him. Henry managed to calm her down and took the gun away.
This domestic turmoil prompted Paulie and Jimmy to intervene, as Karen persistently complained about her husband’s infidelity. They insisted that Henry end the affair and return home, emphasizing that a stable marriage was crucial for maintaining order within their operations. In traditional mafia culture, divorce was frowned upon—members were expected to keep their families intact to prevent any potential leaks of information. To distance Henry from the situation, Paulie assigned him and Jimmy to collect a debt in Tampa, Florida.
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In Tampa, Henry and Jimmy sought payment from a gambler who owed money to their associate. They lured the debtor into a trap, assaulting him to intimidate him into paying. Unbeknownst to them, the victim’s sister worked as an FBI typist. Upon their return to New York, authorities arrested Henry and Jimmy, leading to convictions and prison sentences. While Jimmy served time in a federal prison, Henry was incarcerated in a New York facility alongside Paulie and other associates.
Henry became involved in drug trafficking, smuggling substances into the prison with assistance from his wife, Karen. This operation not only sustained him financially but also led to his own drug addiction. After serving four years, Henry was released and returned to a modest home, having sold their previous residence to cover legal expenses. He promptly visited Paulie, who had also been released.
Noticing Henry’s deteriorated appearance, Paulie sternly warned him to stay away from drug dealings, emphasizing the severe consequences associated with such activities. He also cautioned Henry about Jimmy’s growing ambition and Tommy’s increasingly reckless behavior. Defying Paulie’s advice, Henry established a cocaine distribution network, utilizing connections he had made in prison. He involved various individuals in his operation, including his babysitter, who transported drugs from Pittsburgh concealed in baby bags.
Henry’s associate, Morrie Kessler (Chuck Low), informed him about a lucrative opportunity: the Lufthansa heist, which was poised to become one of the largest cash robberies in American history. Under Jimmy’s meticulous planning, the crew prepared for the operation. Morrie, who had facilitated aspects of the heist, demanded his share of the proceeds, leading to tension within the group.
Henry Hill wasn’t directly involved in the Lufthansa heist; he first heard about Jimmy Conway’s successful operation through radio news, reporting nearly USD 5 million in cash and USD 875,000 in jewelry stolen from the Lufthansa cargo terminal at JFK Airport. During their celebration at the bar, Jimmy seethed as crew members flagrantly displayed their newfound wealth despite his explicit warnings to maintain low profiles. Johnny Roastbeef (John Williams) purchased a flashy pink Cadillac, and another flaunted an expensive fur coat, while Morrie relentlessly pestered Jimmy for his share of the money.
Lufthansa Heist Loose Ends
Amidst this tension, Tommy, with rankie Carbone’s (Frank Sivero)‘s assistance, visited Stacks Edwards (Samuel L. Jackson), their designated getaway driver. After a brief exchange, Tommy coldly shot Stacks in the back of the head in his apartment. The police had found the abandoned truck used in the heist, with Stacks’ fingerprints on the steering wheel. Stacks had failed to dispose of it as planned, instead getting high and crashing at his girlfriend’s place. Jimmy ordered his killing to prevent a potential link to the crew. Stacks murder deeply disturbed Henry, though Jimmy and Tommy remained chillingly unaffected.
Later, word arrived that Tommy had been invited to become a “made man” in an Italian mafia family—a rare honor granting him virtual untouchability. Jimmy was ecstatic about the news. Soon after, Morrie reappeared, again demanding his cut of the money. Despite Henry’s efforts to calm him, Jimmy’s growing paranoia took over. Fearing Morrie’s big mouth might jeopardize everything, and after confirming his chatty tendencies with Henry, Jimmy decided Morrie had to be eliminated.
That night, after some drinks and card games with Morrie, Jimmy, Henry, and Tommy suggested a ride. During the drive, Tommy murdered Morrie by stabbing him in the back of the neck. In the following days, Jimmy began systematically eliminating those involved in the heist. Johnny and his wife were found shot in their car, and Frankie was discovered frozen in a meat truck, among others whose bodies were disposed of unceremoniously.
Months passed, and the Lufthansa heist faded from the headlines. On the day of Tommy’s anticipated induction into the mafia, Jimmy was visibly excited, as having a close friend officially “made” promised greater power and protection. Jimmy and Henry could never be made due to their Irish roots; only those of full Italian descent, traceable through the paternal line, could be officially inducted into the mafia.
Two senior Mafia members picked up Tommy on that fateful day. They escorted him to what appeared to be an empty house for the ceremony. Upon entering, Tommy realized the room was empty and sensed the betrayal. Before he could react, he was executed with a bullet to the head. Tommy died instantly, understanding too late that he had been lured into a trap. Jimmy anxiously awaited news from Tommy, growing increasingly impatient as the hours passed. When he finally called the Mafia family, their response was brutally direct: “Tommy’s dead”. They had exacted revenge for Billy Batts’ murder, and Jimmy understood this savage code of justice all too well.
Sunday, May 11, 1980, 6:55 AM. Henry, now deep in the grip of drug addiction, spotted a helicopter hovering ominously above his home. As he drove off, the helicopter trailed him persistently. A hectic day loomed ahead. First, he needed to deliver guns to Jimmy, then retrieve his brother Michael from the hospital for a home stay. The helicopter shadowed Henry throughout his frantic journey. After hastily preparing dinner with Karen, he collected his merchandise while the helicopter continued tracking his car.
Henry’s paranoia intensified with every passing moment. He met with the Pittsburgh Connection (Paul Herman), who supplied his goods. That night, Lois was scheduled to ship the merchandise to Atlanta. After carefully packaging everything, Henry called Lois from a payphone, instructing her to confirm meeting schedules with customers. He insisted she use a public phone, not her home line. Increasingly anxious, Henry snapped at Lois, who defiantly ignored his warnings. She carelessly revealed departure details on her home phone, which had been tapped.
Arrest, Betrayal, New Life
Henry then continued his rounds. He visited Sandy’s (Debi Mazar) apartment to prepare the merchandise. Afterward, he rejoined his family for dinner. Post-dinner, as Henry readied Lois for her departure, she stubbornly insisted on retrieving her lucky hat from home, refusing to travel without this talisman. Irritated beyond measure, Henry agreed to drive her. However, before he could start the car, police spotlights suddenly surrounded his house. Officers swiftly arrested Henry and Lois in a coordinated sweep.
The narcotics officers had been tracking Henry for an entire month and had tapped all his phones. He now faced a potential 25-year prison sentence, but he feared Jimmy and Paulie’s retribution far more than jail time. He desperately begged Karen to secure his release quickly, knowing that Jimmy and Paulie would inevitably worry he might betray them. Even prison offered little protection, gangsters could easily eliminate targets within those walls. Karen secured Henry’s release by persuading her reluctant mother to mortgage her house for bail money.
Back home, Henry slept clutching a pistol, jumping at every sound. Later, he approached Paulie seeking forgiveness. Paulie erupted in rage, feeling deeply disrespected by Henry’s drug dealing. Eventually, his anger gave way to a mixture of pity and finality. He handed Henry USD 3,200, effectively terminating their long-standing friendship. Realizing the danger he was in, Henry fled home immediately.
Meanwhile, Karen visited Jimmy, who welcomed her with suspicious warmth while subtly probing about Henry’s police interrogation. Jimmy urged her to send Henry to him for a “talk”. After giving Karen some money, he offered her designer Dior dresses supposedly stored in his warehouse. As Karen approached the warehouse entrance, she spotted several suspicious men waiting inside. Her instincts screaming danger, she panicked and bolted straight home.
Days later, Henry reluctantly met Jimmy at a diner as requested. Jimmy casually inquired about Henry’s case and proposed various “solutions”. Then, unexpectedly, Jimmy ordered Henry to assassinate someone in Florida. Throughout their entire relationship, Jimmy had never designated Henry as an executioner—that bloody task had always belonged to Tommy. In that moment, Henry realized with chilling clarity that Jimmy planned to kill him. To survive, Henry made the fateful decision to become an FBI informant and enter witness protection, betraying his former allies.
Henry chose to embrace the mafia’s most fundamental principle: kill or be killed. In court, he methodically exposed Jimmy’s and Paulie’s extensive crimes. The government granted him freedom and relocated him with a new identity. His rock star days in the mob had ended abruptly. Now he lived as an anonymous, ordinary citizen in a modest house with a mortgage and a small yard he could barely maintain.
After eventually leaving witness protection, Henry worked as a chef and later opened his own restaurant called Wiseguys in West Haven, Connecticut, in October 2007. Paulie, whose real name was Paul Vario, died on May 3, 1988, from respiratory failure while incarcerated at Fort Worth Federal Prison in Texas. Jimmy, whose real name was James Burke, died of cancer on April 13, 1996, while serving his sentence at the Roswell Park Cancer Institute in Buffalo, New York.
