Architect Lewis Pilcher designed the death house--it went into service in the early 1920s. The building is still at Sing Sing Penitentiary. On Google Earth, zoom in on the prison and look at the southwest corner by the river. The building with two wings and a diamond-shaped structure in the middle is the infamous "death house".
The Dead End Kids terrorized the set during shooting. They threw other actors off with their ad-libbing, and once cornered co-star Humphrey Bogart and stole his trousers. They didn't figure on James Cagney's street-bred toughness, however. The first time Leo Gorcey pulled an ad-lib on Cagney, the star stiff-armed the young actor right above the nose. From then on the gang behaved.
For years, viewers have wonder whether or not "Rocky" Sullivan (James Cagney) really turned yellow as he was being strapped into the electric chair. Some have wondered if he was faking it in order to keep his promise to Father Jerry. When asked about the scene years later, Cagney says he chose to play it in such a way so that the audience could make their own decisions as to whether or not he was faking.
Some segments of this movie were remade and modified for the feature film Home Alone (1990) and its sequel. In the two movies, Kevin watches them as "Angels with Filthy Souls" and "Angels with Even Filthier Souls".
To play Rocky, James Cagney drew on his memories of growing up in New York's Yorkville, a tough ethnic neighborhood on the upper east side, just south of Spanish Harlem.. His main inspiration was a drug-addicted pimp who stood on a street corner all day hitching his trousers, twitching his neck, and repeating, "Whadda ya hear! Whadda ya say!" Those mannerisms came back to haunt Cagney. He later wrote in his autobiography, "I did those gestures maybe six times in the picture. That was over 30 years ago--and the impressionists have been doing me doing him ever since."
When James Cagney was offered the film, his agent was convinced that he would never agree to play the role of an "abject coward" being dragged to his execution. Cagney, however, was enthusiastic about the chance to play Rocky. He saw it as an opportunity to prove that he had a broad acting range that extended beyond "tough guy" roles.
James Cagney's opening scene with The 'Dead End' Kids took place in the basement of a deserted building. By this time they had been throwing their weight around quite a bit with other directors and actors on the lot. As the scene was being shot, Leo Gorcey jokingly ad-libbed He's psychic!", throwing the rhythm of the scene right out the window. In the next take, just before he said "Come here, suckers", Cagney stiff-armed Gorcey right above the nose. His head went back and hit the kid behind him, stunning them both momentarily. Huntz Hall witnessed the incident and talked about it for many years afterwards.
While filming Rocky's shootout with the police, one scene called for James Cagney to be right at the opening as machine-gun bullets took out the windows above his head. At this point in his career Cagney had experience with the unpredictability of using live gunfire and he later recalled that "common sense or a hunch" made him wary about the upcoming scene, and he finally decided to tell director Michael Curtiz to shoot the scene in process. As Cagney walked away, the professional machine-gunner--a man named Burke--fired the shots. One of the bullets ricocheted, hitting the steel edge of the window and going right through the wall where Cagney's head had been. This experience convinced Cagney that "flirting this way with real bullets was ridiculous".
The moment in which Rocky forces a trailing hood to take his place inside the phone booth in the pharmacy to get killed was inspired by the death of New York gangster Vincent "Mad Dog" Coll. In the real incident, Coll was locked in a gang war with Dutch Schultz. During the war Coll hid in an apartment above a pharmacy and would only come out to go into the pharmacy and call his girlfriend from the phone booth. Schultz found out about this and when Coll went to make his routine phone call, two of Schultz's gunmen walked in and shot Coll to death.
The story was written by Rowland Brown as a project for James Cagney at Grand National Pictures, the independent studio Cagney had signed with in 1936 after winning a breach-of-contract suit against Warner Bros. The original plan had been for Brown to write the full script and direct the film, but when Warners won back Cagney's contract on appeal they bought Brown's story for Cagney but assigned John Wexley and Warren Duff to do the screenplay and Michael Curtiz to direct.
James Cagney's other inspiration for Rocky was his childhood friend, Peter "Bootah" Hessling, who was convicted of murder and "sent to the electric chair" on July 21, 1927. The night Bootah was executed, Cagney was playing in a Broadway show and wept upon hearing of his friend's death.
Analysts claim that if it weren't for this film and two other films directed by Michael Curtiz that year (The Adventures of Robin Hood (1938) and Four Daughters (1938)), Warner Bros. would have lost a considerable amount of money, resulting in negative turnover for the company's 1938 fiscal year.
Rowland Brown's story was revised a number times by John Wexley and Warren Duff. They provided "powerful treatments", but as with many of the "catch-as-catch-can" pictures of the time, the screenplay was "insubstantial". James Cagney later recalled: "the actors had to patch up [the script] here and there by improvising right on the set".