Henry Hill grew up in a poor working class family in Williamsburg, Brooklyn, then a largely Italian-Jewish neighborhood. His father, Henry Hill, Sr., was an Irish-American electrician, and his mother, Carmella Hill, was an Italian Sicilian-American. Henry and his seven siblings lived in a small house. From an early age he admired the local mafiosi that socialized across the street from his home, which included Paul Vario, a capo in the Lucchese crime family. In his early teens, he began running errands at Vario's cabstand, shoe shine stand, and pizzeria.
Hill's first experience in gang life began parking cars and doing other odd jobs for the Lucchese crime family. Henry stopped going to school soon after to pursue a life of a gangster. Hill's first arrest came when he attempted to use a stolen credit card to buy tires at a Texaco gas station. Refusing to say anything to the police, he earned the respect of Lucchese Family associate Jimmy Burke, who saw great potential in young Henry. Hill soon dropped out of high school to devote all his time to working for gangsters. Burke, like Hill, was unable to become a made member of the Mafia due to his Irish ancestry, but the Mafia was happy to have associates of any ethnic background as long as they made money and did not cooperate with the authorities.
In 1960, Hill joined the Army and was stationed at Fort Bragg, near Fayetteville, North Carolina, for three years. He was a member of the 82nd Airborne paratrooper unit there, but maintained contact with Vario and his other friends in New York throughout his enlistment. Hill continued to hustle while in the service, selling extra food, loan sharking salary advances to his fellow soldiers, and selling tax-free cigarettes. Before being discharged, Hill spent two months in a military stockade for brawling and stealing a sheriff's car.
In 1963, he returned to New York, beginning the most notorious phase of his criminal career. Hill, along with Burke and Tommy DeSimone, and others in Burke's Robert's Lounge crew, hijacked trucks, sold stolen goods, imported and sold untaxed cigarettes, engaged in loan sharking and bookmaking, and planned airport robberies, carrying out the Air France Robbery in 1967 and the huge Lufthansa heist in 1978, as well as committing numerous mob-related murders.The Lufthansa score was put together after Vario lost several millions in a failed cocaine deal (viz theresa ferrara).
In 1965, Hill met his wife, Karen. The two first eloped to North Carolina where they had a large wedding, to which most of Hill's gangster friends were invited. After the birth of their two children they rented an apartment in a two-family home in Island Park, New York (1968).
 Fallout between Hill, Vario, and Burke
Hill was paroled in 1978 after serving six years of a ten-year prison sentence for extortion. Hill and Burke had severely beaten and pistol-whipped a gambler in Tampa, Florida (Gaspar Ciacco) who owed union official friends of theirs (Luis and Raul Charbonier) a large gambling debt. Burke was also released on parole around the same time as Hill.
While in prison, Hill had made contact with a Pittsburgh drug dealer named Paul Mazzei. Hill had sold drugs while in prison to help support his wife and two children on the outside. After his parole, Vario revealed that he knew about Hill's drug dealing in prison and warned him not to continue with this now that he was out. Vario strongly opposed the trade of drugs in his crew because prison sentences imposed on anyone convicted of drug trafficking were so lengthy that the accused would often become informants in exchange for a lighter sentence. Hill nevertheless started a major interstate drug trafficking operation with Mazzei, the potential to earn large amounts of money being too great to resist.
Hill began wholesaling marijuana, cocaine, heroin, and quaaludes, earning enormous amounts of money. After the murders of several of his friends by Burke, following the Lufthansa Heist, and the disappearance of his close friend Tommy DeSimone, who, Hill believed, had been delivered by Vario into the hands of (and murdered by,) the Gambino crime family for killing two made members without permission, he became increasingly paranoid.
Hill and Mazzei also set up a point shaving scheme, which was put in place when Mazzei convinced Boston College center Rick Kuhn to participate. Kuhn encouraged teammates to join the scheme, which became a scandal. Hill also claimed to have an NBA referee who worked games at Madison Square Garden during the seventies in his pocket because of the debt the referee had accrued gambling on horse races.
In 1980, Hill was arrested on a narcotics trafficking charge, bonded out of jail, and shortly afterwards, was re-arrested as a material witness in the Lufthansa robbery. He became convinced that his former associates planned to have him killed: Vario, for dealing drugs, and Burke, to prevent Hill from implicating him in the Lufthansa robbery. This was confirmed by a surveillance tape played to Hill by federal investigators, in which Burke tells Vario of their need to have Hill "whacked."