From an early age, Hill admired the local mobsters who socialized at a dispatch cabstand across the street from his home, a group that included Paul Vario, a caporegime (captain) in the Lucchese crime family.

[6] In his early teens, Hill began running errands for patrons at the cabstand and Vario's other front businesses.

It was in this capacity that 13-year-old Hill first met notorious hijacker and Lucchese family associate James "Jimmy the Gent" Burke in 1956.

Hill served drinks and sandwiches at a card game and was dazzled by Burke's openhanded tipping: "He was sawbucking me to death.

Hill would be a "no show" and put on a building contractor's construction payroll, guaranteeing him a weekly salary of $190 (equivalent to $2,060 in 2023).

The card also allowed Hill to facilitate the pickup of daily policy bets and loan payments to Vario from local construction sites.

[11] Hill and Lenny, who was of the same age, had attempted to use a stolen credit card to buy snow tires for Tuddy's wife.

The Vario crew, however, were happy to have associates of any ethnicity, so long as they made money and refused to cooperate with authorities.

[12] In June 1960, at age 17, Hill joined the United States Army, serving with the 82nd Airborne Division at Fort Bragg in North Carolina.

Before his discharge, Hill spent two months in the stockade for stealing a local sheriff's car and brawling in a bar with Marines and a civilian.

In 1963 he returned to New York and began the most notorious phase of his criminal career: arson, intimidation,[14] running an organized stolen car ring,[15] and hijacking trucks.

[7] The theft was not discovered until the following Monday, when a Wells Fargo truck arrived to pick up the cash to be delivered to the French American Banking Corporation.

[7] Hill used his share of the robbery proceeds to purchase a restaurant on Queens Boulevard, called The Suite, initially aiming to run it as a legitimate business and provide distance between himself and his mob associates.

[19] According to the book Wiseguy, after William "Billy Batts" Bentvena was released from prison in 1970, a welcome-home party was thrown for him at Robert's Lounge, which was owned by Burke.

They started to hear sounds from the trunk, and when they realized that Bentvena was still alive, DeSimone and Burke stopped the car and beat him to death with the shovel and a tire iron.

[7] In Wiseguy, Hill said the body was eventually crushed in a car crusher at a New Jersey junkyard, which was owned by Clyde Brooks.

However, on the commentary for the film Goodfellas, Hill states that Bentvena's body was buried in the basement of Robert's Lounge, a bar and restaurant owned by Burke, and only later was put into the car crusher.

[20][21] Hill was imprisoned with Vario, who was serving a sentence for tax evasion, and several members of John Gotti's Gambino crew.

He began trafficking in drugs, which Burke eventually became involved with, even though the Lucchese family did not authorize any of its members to engage in such activity.

[24] Hill began wholesaling marijuana, cocaine, heroin and quaaludes based on connections he made in prison, making enormous amounts of money.

However, a young child who acted as a mule of Hill's "ratted" him out to narcotics detectives Daniel Mann and William Broder.

[26] The plot had begun when bookmaker Martin Krugman told Hill that Lufthansa flew in currency to its cargo terminal at the airport; Burke set the plan in motion.

[19] 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 heist.

[19] Edward A. McDonald, the head of the Brooklyn Organized Crime Strike Force, arrested Hill as a material witness in the Lufthansa robbery.

[32][33] Paul Vario received four years for helping Henry Hill obtain a no-show job to get him paroled from prison.

[46][47] Driving to and from the set, Liotta listened to FBI audio cassette tapes of Hill, so he could practice speaking like his real-life counterpart.

[48] The 1990 film My Blue Heaven was based on Hill's life, with the screenplay written by Pileggi's wife Nora Ephron.

In the episode, Hill recounts his life of crime, as well as his close relationship with Jimmy Burke and the illegal activity the two engaged in together.

[55] In 2014, the ESPN-produced 30 for 30 series debuted Playing for the Mob,[56] the story about how Hill and his Pittsburgh associates, and several Boston College basketball players, committed the point-shaving scandal during the 1978–79 season, an episode briefly mentioned in the movie.

[59] Hill died of complications related to heart disease in a Los Angeles hospital, on June 12, 2012, after a long battle with his illness, a day after his 69th birthday.