Michael Madsen impulsively proposed to, and married, DeAnna Madsen during a two-day break in filming. According to Michael Madsen, Al Pacino was disgusted by his impulsiveness. The Madsens remain happily married.
Donnie bets his kids twenty dollars that they can't get through breakfast without saying three words, and his daughter replies "you lose." The scene is based on a famous incident involving writer Dorothy Parker and President Calvin Coolidge, known as "Silent Cal" for his quiet manner and hatred of small talk. Parker, seated next to Coolidge, turned to him and said "Mr. Coolidge, I've made a bet against a fellow who said it was impossible to get more than two words out of you." Coolidge allegedly replied "You lose."
Joseph D. Pistone said in an interview in the special features on the DVD, that he was suppose to be undercover for a few months. It ended up being six years. His family was moved across the country after nine months. He rarely saw them.
Director Mike Newell recalled that the first scene Pacino and Depp had together was a scene in a car where they discuss 'Lefty' possibly getting out of the mob at 'Pistone's' suggestion. During several takes, Depp would fart very loudly, ruining the scene and causing Pacino to become increasingly angry with Depp. Eventually, Depp reached under his seat and pulled out a whoopee cushion that he had been using. Pacino broke up laughing and Newell realised it was Depp's intention to break the ice and tension between the actors and the two stars subsequently had a close relationship and friendship for the rest of the shoot.
During the montage which accompanies the song "Happiness" there is a brief shot of a panel truck exiting a garage bay under the Manhattan Bridge Overpass. The bay is part of Chambers Paper Fibers Corp which was the real-life site of NYPD Detective Rick Cowan's sting operation, which took down the Mafia garbage cartels in New York City (Operation Wasteland.) These exploits are detailed in his book "Takedown." The use of the location had to be intentional, the trials of the heads of the garbage cartels occurred in the same year as the film's release, 1997.
Delayed from a Christmas 1996 release date to February, with hopes that Sony would give the film an Oscar campaign. However, their slate for the awards season was already abundant with films they felt had better chances: Jerry Maguire (1996), The People vs. Larry Flynt (1996), and The Mirror Has Two Faces (1996) all successfully earning a slew of nominations.
The trivia items below may give away important plot points.
The movie ends with the implication that Lefty was killed after being "sent for". In real-life, the FBI intercepted Lefty on the way to being killed, and arrested him. Sonny Black was "sent for" and murdered. His body was found on Staten Island a year later. Joe Massino, who orchestrated his murder, was convicted in 2005. Lefty was convicted of conspiracy to commit murder, extortion, distribution of a controlled dangerous substance, and running an illegal gambling operation. He was sentenced to twenty years in prison, but received early parole in 1992, after it he was diagnosed with terminal lung cancer. He died in 1994.
In one of the final scenes, Lefty is seen taking off his jewellery after he has been sent for, knowing he would be killed. In real-life, Sonny Black was sent for and killed after he took off his jewellery and gave it to his favorite bartender, knowing he would be killed.
Because he was so convincing in his undercover persona, the Bonanno family was seriously considering "making" Joe Pistone (for example, fully initiating him into the mob) before they learned he was an FBI Agent.
Bruno Kirby portrays the character "Nicky", who is killed by Lefty after the three capos murder. In real life Nicholas Santora, the real-life counterpart of Nicky, was not killed and is thought to be the underboss of the Bonanno crime family.