U-571 (2000) - 48 mistakes
Directed by Jonathan Mostow, starring Bill Paxton, David Keith, Harvey Keitel, Jake Weber, Jon Bon Jovi, Thomas Kretschmann
Factual error: U-571 was sunk on January 8, 1944, by an Australian Sunderland. She was previously damaged by an Allied destroyer on March 22, 1943, but managed to come back to the base. All supply submarines (Type XIV or Type VIIF) were actually sunk by Allied planes or surface ships. I know that the movie is entertaining rather than historical, but why didn't the movie makers choose boats that disappeared without a trace instead?
Plot hole: The submarine gets buzzed by a single engine German fighter. They are somewhere between the US coast and Greenland. The Germans had no aircraft carriers nor bases in the area. Since it was not a float plane how did the fighter get there? It could not possibly have flown the several thousand miles from continental Europe.
Continuity: When the German destroyer is with U-571, look at the ship. Notice in the first shots there are 2 gun turrets on either side. Yet in the later shots during the final battle there's only one turret. In addition, right before the turrets are shown turning to fire, look at the ship again - they are already aimed at the U-boat. I guess the Germans felt the need to do this two times.
Continuity: Just after shooting the radio room on the German destroyer, U-571 submerges so quickly that the sailors do not manage to plug the gun. After a few moments when the boat goes from 180 to 200 meters there is a short shot from the above when we can clearly see that the gun is perfectly plugged.
Factual error: When the marine commando shows the sailor his "luggage" (the boxes of explosives) to be loaded onto the submarine, some of the boxes have orange Explosive B placards. Those are Dept. of Transportation placards. The D.O.T. didn't exist until 1966 and the placards were not used until later than that.
Factual error: In the film U-751 the torpedoes were shown leaving a trail of bubbles behind them. The type of torpedo which did that was the G7a 'T1' torpedo - which was pre-war issue. At the time of the film the standard torpedo of the Ubootwaffe was the improved G7e 'T2' torpedo which did not leave a trail of bubbles due to a different motor design.
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