- Anachronisms: Parts of the American flag are visible in Michael Jr.'s school. From the spacing of the visible stars, the flag clearly has 50 stars, not the 48 it would have had in the 1930s.
- Anachronisms: When Michael and his son first arrive in Chicago, there is a brief shot of bright silver metal cars on the El. They were introduced in the 1980s. In 1931, the cars would have been made of wood and painted dark brown.
- Anachronisms: Michael Jr. reads "The Lone Ranger" in 1931. It was created for radio in 1933; the books were published even later.
- Revealing mistakes: When Sullivan and his son drive off the road after the diner scene, tire tracks are already there from previous takes.
- Continuity: The bullet hole in the rear window of the Sullivan's car disappears and reappears.
- Anachronisms: When Michael and his son first arrive in Chicago, a brief shot shows their car traveling into town. In the Chicago skyline, half of a (skyscraper) construction sky crane can be seen at a distance.
- Anachronisms: In the opening credits, a high-voltage power line tower is in the background. They didn't exist in 1931.
- Anachronisms: The Catholic clergy's vestments have a more modern "poncho" style chasuble. In the 1930s, they would have worn the "fiddle-back" style.
- Anachronisms: In diner scene, the ashtray on Maguire's table is modern pressed metal. In 1931, it would have been glass or ceramic.
- Anachronisms: The music playing in the background during the diner scene is "Queer Notions", which was recorded in 1933.
- Anachronisms: When Mike Sullivan walks through the nightclub to get information from the owner, the club members are wearing "Flappers" and "Sheiks." Both were very popular clothing styles from 1925 to 1928. In 1931, they were considered outdated.
- Errors in geography: In the diner scene, a bottle of HP Sauce is on Sullivan's table. HP Sauce is available almost exclusively in the United Kingdom; it wouldn't have been in an average American roadside diner in 1931.
- Anachronisms: The Englewood Diner is a 1941 Sterling Diner built by J.B. Judkins of Merrimack, Massachusetts. The Judkins company started building diners in 1936.
- Anachronisms: While driving into Chicago, Sullivan passes an athletic field with modern outdoor lighting.
- Continuity: Maguire's coffee cup magically appears between shots.
- Continuity: The heavy rain storm that occurs that fateful night doesn't appear to wash away the snow. The snow outside the Sullivan's house can be seen the next morning to be the same as it was before, even with well-worn tyre tracks in it!
- Continuity: When Sullivan leaves, the garage doors are open at an angle, and he doesn't close them. When he returns, the doors are perfectly straight as he backs in.
- Continuity: The bullet removed from Sullivan's arm has no rifling marks, and appears to be .45 caliber, rather than the .32 that Maguire was using.
- Audio/visual unsynchronized: During the shoot-out in Mr. Rance's hotel suite, Sullivan shoots at Maguire from behind the empty trunk. The reports heard from his .45 pistol are out of sync with the shots he fires.
- Continuity: In the first scene with Connor, the first shot shows his cigarette with a long build-up of ash on the end. In the very next shot, however, the cigarette has regenerated to near-full length, with very little ash.
- Continuity: When Mr. Rooney speaks to the crowd at the wake, he initially stands on a chair. In the next shot, he stands beside the chair, which is sideways to the crowd. In the next shot, the chair is facing the crowd.
- Continuity: When Michael, Sr. is assembling the Thompson submachine gun, in the overhead view, the magazine is on the table to the right of the case. After Michael, Jr. walks in, the magazine is no longer on the table. As he turns, we see that it's not mounted on the gun, either.
- Anachronisms: Walking Liberty half dollars were not produced in 1930, 1931, or 1932. The Walking Liberty half dollar that Harlan McGuire laces between his fingers is much too worn for a coin as little as two years old.
>>> WARNING: Here Be Spoilers <<<
Goofs below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- Boom mic visible: SPOILER: Reflected in the window of Michael's first bank robbery.
- Revealing mistakes: SPOILER: When Michael Sullivan shoots Connor Rooney in the bathtub, he fires his .45 pistol three times, and three shell casings hit the floor. When he fired the shots, the slide of the pistol never retracted, so the chamber never actually opened to eject the spent bullet shells.
- Revealing mistakes: SPOILER: When Michael Sullivan is in the car with Michael Jr. before he robs a bank, he puts the pistol slide forward, then pulls the slide back again. By doing that, he would have sent the first round out of the chamber.
- Revealing mistakes: SPOILER: When Michael is shot in the back at the beach house, the bullets exit his chest, but they don't break the grass window.
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