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As far back as I can remember, I always wanted to be a gangster.
~ Henry's famous quote.
I swear on my f**king mother! If you touch her again, YOU'RE DEAD!
~ Henry beating up a neighbor for sexually harassing and beating up his then future wife Karen.
I'm an average nobody. I get to live the rest of my life like a schnook.
~ Henry being forced out of the gangster life and now has to face living life like a normal citizen and his last quote in the film.
In 1955, high school student Henry Hill becomes enamored of the gangland life in his neighborhood and begins working for mob boss Paul "Paulie" Cicero and his associates: James "Jimmy the Gent" Conway, an infamous truck hijacker; and Tommy DeVito, a fellow juvenile delinquent. Henry begins as a fence for Jimmy, gradually working his way up to more serious crimes, and also becomes close friends with Tommy in the process. Enjoying the perks of their criminal life, the three associates spend most of their nights in the 1960s at the Copacabana nightclub, carousing with women. Henry starts dating Karen Friedman, a Jewish woman from the Five Towns area of Long Island. Initially troubled by Henry's criminal activities, Karen is eventually seduced by his glamorous lifestyle; the pair eventually get married despite her parents' disapproval.
In 1970, Gambino family member Billy Batts repeatedly insults Tommy at a nightclub - owned by Henry - over his past as a shoe-shine boy. Enraged, Tommy and Jimmy kill him while Henry closes the doors to keep people from hearing him. The murder of a made man would warrant retribution from the Gambino mafia; another made man, possibly even Paulie, would be forced to kill the perpetrators. Realizing this, Jimmy authorozes Henry and Tommy to cover up the murder. They transport the body in the trunk of Henry's car and bury it in upstate New York. Six months later, Jimmy learns that the burial site is slated for development - this forces the trio to exhume and relocate the decomposing corpse, which makes Henry vomit from the smell in the process.
Henry later cheats on Karen with Janice. When Karen finds out about their affair, she tries to confront Janice and then threatens Henry at gunpoint. When Henry moves in with Janice afterwards, Paulie gets involved and tells him to go back to Karen after helping Jimmy retrieve a debt from a gambler in Tampa. When the pair return, however, Henry and Jimmy are arrested and both receive a 10-year parole.
During his time in prison, Henry has drugs smuggled in by Karen and sells them to a fellow inmate from Pittsburgh in order to support the family. He is eventually paroled 4 years later. During his welcome home party, Paulie warns Henry to stay away from drugs so that the crew doesn't risk facing further criminal charges; Pauline also warns Henry about his associates, noting that Jimmy has been growing overambitious and that Tommy is getting out of control with the extent of their criminal activities. But Henry doesn't listen to Paulie's orders to prevent drug trafficking and expands the cocaine business, eventually involving Jimmy and Tommy without Paulie's knowledge.
Soon enough, Henry becomes involved with Jimmy's plan to commit the Lufthansa heist at John F. Kennedy International Airport. The heist is successful as the crew manages to steal $6 million. However, when some members of the crew end up buying expensive items such as a car and a fur coat against Jimmy's orders, Jimmy becomes furious and lashes out at them in front of Harry. Thereafter Jimmy begins to have most of the crew killed after their getaway vehicle is found by the police. At one point Henry buys an expensive Christmas tree (the most expensive Christmas tree at the store) for his family for Christmas, but he doesn't get caught for it.
Not long afterwards, Henry learns from Jimmy that Tommy is due to become a made man within a few days time. When the day eventually arrives, however, Tommy ends up getting killed by the people who were supposed to take him to the ceremony; it turns out that the made-man ceremony was actually a ruse in order for Tommy, having been fooled into thinking he would become a made man, to be lured into a trap and eventually killed in retribution for Batts' murder. Jimmy and Henry are devastated to learn about this as they await for the news at a phone box near a cafe.
By May 11, 1980, Henry has become a nervous wreck from cocaine use and insomnia. He tries to organize a drug deal with his associates in Pittsburgh, which the mafia was against as it was a dangerous business. But in the end Henry brings police attention on him and ends up getting arrested by narcotics agents. After being jailed and later bailed out of custody, he discovers the $60,000 worth of cocaine has gone missing and realizes that Karen flushed the cocaine down the toilet so that the police would not find incriminating evidence against Henry. In response, Henry gets angry with Karen as her actions have unwittingly left the family penniless and ends up having a mental breakdown.
When Henry approaches Pauline for help, Paulie - having learned that Henry went against his orders - angrily berates him for his betrayal. A guilt-ridden Henry apologizes and once again pleads Pauline for help. Paulie reluctantly gives him £3,200, but then disowns him and their association upon saying to him "Now I gotta turn my back on you". Later on Henry meets up with Jimmy at the cafe and is given an assignment that would mean whacking someone. This causes Henry to realize that Jimmy actually plans to have him killed. Furthermore, he learns from Karen that Jimmy had ostensibly tried to have her killed when they recently encountered each other.
With the prospects of facing federal charges as well as Jimmy's plans to have him and Karen eliminated, Henry decides to enroll in the Witness Protection Program and become an FBI informant. He gives sufficient testimony to have Paulie and Jimmy arrested on criminal charges; both Paulie and Jimmy are subsequently trialed and ultimately convicted for their criminality.
Soon afterwards, Henry - now out of his gangster life - is forced to live like a normal citizen. He narrates: "I'm an average nobody. I get to live the rest of my life like a schnook".
The ending reveals that Henry is still in the Witness Protection Program. In 1987, he was arrested in Seattle, Washington for narcotics conspiracy and ended up receiving 5 years probation. Since 1987, Henry has been clean. Later on Henry and Karen Hill separated in 1989 after 25 years of marriage.
Henry is the most principled character throughout the movie, in spite of being an amoral gangster. His moral fiber is not that flexible when compared to the rest of his partners. It's established early on, during his teenage years, when he helps to bandage the arm of a man who had been shot and is berated for wasting good aprons. Likewise, he does care for those around him. Henry is genuinely worried about Morrie and does his best to calm him down, because Henry knows that Jimmy is willing to beat the guy senseless if he keeps complaining. When he discovers that their next door neighbor sexually assaulted Karen, Henry breaks the man's nose at gunpoint.