- Actor-Inspired Element: It was Sean Connery's idea to film the "blood oath" scene between Ness and Malone in a Catholic church. Originally it was going to take place on the street (in the same scene that follows the church scene). Connery felt that a church would be the only "safe" place in Chicago where the two characters would make such a commitment to fight Al Capone.
- California Doubling: The Canadian Border raid was filmed at Hardin, Montana, which is about as far away from the Canadian border as you can get while still being in Montana.
- Cast the Runner-Up: Andy García was originally considered for Frank Nitti. He insisted on reading for George Stone instead.
- Dawson Casting: Robert De Niro was 43 at the time of filming, playing Al Capone, who was 31–32 at the time of the movie's events.
- Dyeing for Your Art / Method Acting: Robert De Niro gained 30 pounds for his role as Capone, and (allegedly) even insisted on wearing the same clothes Capone did, right down to his silk underwear.
- Enforced Method Acting: For his death scene, Sean Connery did not expect the squibs to be as explosive as they were. After the first take, he was taken to the hospital with dust and fake blood in his eyes.
- Fake Irish: Edinburgh-born Sean Connery as Jimmy Malone.
- Fake Nationality: Havana-born Andy García as an Italian-American (first generation), and the Kansas-born Chiricahua Apache/Romani Billy Drago as an Italian.
- On-Set Injury: Sean Connery was hospitalized after filming his death scene when fake blood from the squibs went in his eyes. Brian De Palma had to beg Connery to do another take.
- Real-Life Relative: The baby in the carriage at the train station is the film's stunt coordinator's son.
- Referenced by...: The Super Mario Bros. Super Show! parodies the film in "The Unzappables", in which Mario, Luigi, Princess Toadstool, and Toad butt heads with King Koopa, who takes on the alias "Al Koopone," in Crime Land, a pastiche of Prohibition-era Chicago.
- Star-Making Role: For Kevin Costner and Andy García.
- Throw It In!: Kevin Costner ad-libbed the line "He's in the car," after throwing Nitti off of the roof.
- What Could Have Been:
- Mel Gibson turned the role of Eliot Ness down in order to star in Lethal Weapon. Other candidates were Alec Baldwin, Tom Berenger, Jeff Bridges, Nicolas Cage, Michael Douglas, Harrison Ford, Gene Hackman, Rutger Hauer, Ed Harris, William Hurt, Don Johnson, Tommy Lee Jones, Michael Keaton, Christopher Lambert, Stephen Lang, John Malkovich, Jack Nicholson, Nick Nolte, Ron Perlman, Mickey Rourke, Kurt Russell, Arnold Schwarzenegger, Sylvester Stallone, John Travolta, James Woods and Bruce Willis.
- Suffolk-born Bob Hoskins was cast as Al Capone, but was paid a bundle of money once Brian De Palma brought Robert De Niro, the director's first choice all along, onboard.
- Bridges and Hackman were offered the role of Malone.
- Mary Elizabeth Mastrantonio was considered for Catherine Ness. Interestingly, she actually would end up playing Costner's love interest in another movie a few years later.
- In the original script, the final gunfight had Eliot Ness and George Stone battling Capone gunmen on a stopped train. Brian De Palma conceived the gunfight on the steps in Chicago's Union Station when Paramount decided that staging the scene and finding a 1930s period train would be too expensive.
- There was originally a different ending for the movie. It was to have been a scene with the camera shooting a close-up of Capone's face as it is being warmed up for a shave. And then the camera would have craned up to show the audience that he has reporters around him, but he is in his jail cell.
- Michael Jackson wrote the song "Al Capone" for the film. Once it was turned down, Jackson, reworked it as "Smooth Criminal" and included it in his album Bad.
- Cinematographer Stephen H. Burum originally wanted to shoot the film in black & white.
- Writing by the Seat of Your Pants: Brian De Palma said that when he was filming the scene in the train station, he made up a series of shots as the scene was being filmed.
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