Henry Hill, Jr. was born on June 11, 1943 in Manhattan, New York, to Henry Hill, Sr., an Irish immigrant and electrician, and Carmela Costa Hill, a Sicilian. The working-class family consisted of Henry and his eight siblings who grew up in Brownsville, a poorer area of the East New York section of Brooklyn. From an early age, Hill admired the local mobsters who socialized across the street from his home, including Paul Vario, a capo in the Lucchese crime family. In 1955, when Hill was 11 years old, he wandered into the cabstand across the street looking for a part-time after-school job. In his early teens, he began running errands for patrons of Vario's storefront shoeshine, pizzeria, and dispatch cabstand. He first met the notorious hijacker and Lucchese family associate James "Jimmy the Gent" Burke in 1956. The 13-year-old Hill served drinks and sandwiches at a card game and was dazzled by Burke's openhanded tipping. "He was sawbucking me to death. Twenty here. Twenty there. He wasn't like anyone else I had ever met."

In June 1960, Hill joined the Army, serving with the 82nd Airborne Division at Fort Bragg in North Carolina. Hill claimed the timing was deliberate; the FBI investigation into the 1957 Apalachin mob summit meeting had prompted a Senate investigation into organized crime, and its links with businesses and unions. This resulted in the publication of a list of nearly 5,000 names of members and associates of the five major crime families. Hill searched through a partial list but could not find Vario listed among the Lucchese family.

Throughout his three-year enlistment, Hill maintained his mob contacts. He also continued to hustle: in charge of kitchen detail, he sold surplus food, loan sharked pay advances to fellow Soldiers, and sold tax-free cigarettes. Before his discharge, Hill spent two months in the stockade for stealing a local sheriff's car, and brawling in a bar with a civilian and Marines. In 1963, Hill returned to New York and began the most notorious phase of his Criminal career: arson, intimidation, running an organized stolen car ring, and hijacking trucks.

In 1965, Hill met his Future wife, Karen Friedman, through Paul Vario, Jr. Paul insisted that Hill accompany him on a double date at Frank "Frankie the Wop" Manzo's restaurant, Villa Capra. According to Friedman the date was disastrous, and Hill stood her up at the next dinner date. Afterward, the two began going on dates at the Copacabana and other nightclubs, where Friedman was introduced to Hill's outwardly impressive lifestyle. The two later got married in a large North Carolina wedding, attended by most of Hill's gangster friends.

On April 7, 1967 Hill and Tommy DeSimone executed the Air France robbery following a tip-off from Robert "Frenchy" McMahon. The robbery was initially proposed to Hill in January 1967 as an armed heist of several bags containing $60,000 each from the Air France cargo terminal at John F. Kennedy International Airport. The targeted money was stored in a strong-room inside the Air France cargo hold, permanently protected by a security guard. Hill determined that an armed robbery would involve unnecessary risk and would be unlikely to succeed; instead, Hill devised a plan to steal the keys to the strong room from a security guard who carried them at all times. Hill conducted surveillance on the security guard during his leisure time and found the guard had a weakness for women. Hill and McMahon succeeded in getting the guard drunk before driving him to the Jade East Motel where he was introduced to a prostitute. While the guard was distracted, Hill retrieved the guard's set of keys from his discarded trousers and had copies made before returning the original keys, thus leaving the guard and his employers unaware of any breach in security. Hill entered the cargo terminal with Tommy DeSimone on April 7, 1967 following a tip-off from McMahon about a shipment of between $400,000 and $700,000 being made to the strong-room. Using the duplicate key, Hill and DeSimone stole $420,000 (equivalent to over $3.1 million in 2018) in cash from the strong-room, loading the money into a large suitcase. They entered and exited the cargo terminal unchallenged and unnoticed while the security guard was on a meal break. No shots were fired and the money was not reported missing until April 11, 1967. Hill shared the take from the heist with senior Mafia members, giving $120,000 in total to Paul Vario and Sebastian Aloi of the Columbo crime family, in recognition that the cargo terminal fell within the Columbo family's 'turf'.

Hill also claimed to have an NBA Referee in his pocket who worked games at Madison Square Garden during the 1970s. The Referee had incurred gambling debts on horse races.

Henry Hill collaborated with the Novelist Daniel Simone in writing and developing a non-fiction book titled, The Lufthansa Heist, a portrayal of the famous 1978 Lufthansa Airline robbery at Kennedy Airport.

Hill, his wife Karen, and their two children (Gregg and Gina) entered the U.S. Marshals' Witness Protection Program in 1980, changed their names, and moved to undisclosed locations in Omaha, Nebraska; Independence, Kentucky; Redmond, Washington; and Seattle, Washington. In Seattle, Hill hosted backyard cookouts for his neighbors, and on one occasion, while under the influence of a combination of liquor and drugs, he revealed his true identity to his guests. To the ire of the federal Marshals, they were forced to relocate him one final time to Sarasota, Florida. There, a few months had passed, and Hill repeated the same breach of security, causing the government to finally expel him from the Federal Witness Protection Program.

Paul Vario received four years for helping Henry Hill obtain a no-show job to get him paroled from prison. Vario was also later sentenced to ten years in prison for the extortion of air freight companies at JFK Airport. He died of respiratory failure on November 22, 1988, at age 73 while incarcerated in the FCI Federal Prison in Fort Worth.

Goodfellas, the 1990 Martin Scorsese-directed crime film adaptation of the 1986 non-fiction book Wiseguy by Nicholas Pileggi, follows the 1955 to 1980 rise and fall of Hill and his Lucchese crime family associates. Scorsese initially named the film Wise Guy but subsequently, with Pileggi's agreement, changed the name to Goodfellas to avoid confusion with the unrelated television crime drama Wiseguy. To prepare for their roles in the film, the actors often spoke with Pileggi, who shared research material he gathered while writing the book. The Director made transcripts of these sessions, took the lines he liked best, and put them into a revised script the cast worked from during principal photography.

Jimmy Burke was given 20 years in prison for the 1978–79 Boston College point shaving scandal, involving fixing Boston College basketball games. Burke was also later sentenced to life in prison for the murder of scam Artist Richard Eaton. Burke died of lung cancer while serving his life sentence, on April 13, 1996, at the age of 64.

Hill was arrested in 2001 on narcotics-related charges in Seattle, where he was living in the Wedgwood neighborhood under the name of Alex Canclini. In 1990, his wife Karen had filed for divorce after 23 years of marriage. The divorce was finalized in 2002. Due to his numerous crimes while in witness protection, Hill (along with his wife) were expelled from the program in the early 1990s.

In October 2002, Hill published The Wiseguy Cookbook: My Favorite Recipes From My Life As a Goodfella To Cooking On the Run. In it, Hill shared some stories throughout his childhood, life in the mob, and running from the law. He also presents recipes he learned from his family, during his years in the mob, and some that he came up with himself. For Example, Hill claimed his last meal the day he was busted for drugs consisted of rolled veal cutlets, sauce with pork butt, veal shanks, ziti, and green beans with olive oil and garlic.

In 2006, Hill and Ray Liotta appeared in a photo shoot for Entertainment Weekly. At Liotta's urging, Hill entered alcohol rehabilitation two days after the shoot.

Hill worked for a time as a chef at an Italian restaurant in Nebraska, and his spaghetti sauce, Sunday Gravy, was marketed over the internet. Hill opened another restaurant, Wiseguys, in West Haven, Connecticut, in October 2007.

In 2008, Hill was featured in episode 3 of the crime documentary series The Irish Mob. 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. A large portion of the segment focuses on Burke's and Hill's involvements in the famous Lufthansa Heist. The entire series is currently available on Netfilx.

After his 2001 arrest, Hill claimed to be clean until he was arrested again in North Platte, Nebraska, in March 2002. Hill had left his luggage at Lee Bird Field Airport in North Platte, Nebraska, containing drug paraphernalia, glass tubes with cocaine and methamphetamine residue. In September 2005, he was sentenced to 180 days imprisonment for attempted methamphetamine possession. Hill was sentenced to four years' probation on March 26. On December 14, 2009, he was arrested in Fairview Heights, Illinois, for disorderly conduct and resisting arrest, which Hill attributed to his drinking problems.

In 2004, Hill was interviewed by Charlie Rose for 60 Minutes. In 2010, Hill was inducted in the Museum of the American Gangster in New York City. On June 8, 2011, a show about Hill's life aired on the National Geographic Channel's Locked up Abroad.

Hill died of complications related to heart disease in a Los Angeles hospital, on June 12, 2012, after a long battle with his illness, only a day after his 69th birthday. His girlfriend for the last 14 years of his life, Lisa Caserta, said, "He had been sick for a long time....his heart gave out". CBS News reported Caserta's saying: "he went out pretty peacefully, for a goodfella". She said Hill had recently suffered a heart attack before his death and died of complications after a long history of heart problems associated with smoking. Hill's family was present when he died. Hill was cremated the day after his death.

On October 7, 2014, Hill was featured on ESPN Films' 30 for 30: "Playing for the Mob". In the documentary episode, based on the fixing of the Boston College basketball games in 1978 and 1979, Hill reveals the details behind the point shaving scandal along with the testimony from the players and federal investigators involved. Ray Liotta also guest starred, as the narrator.