* Edward G. Robinson: Robinson, known for his portrayals of tough and witty gangsters, frequently used the phrase "wise guy" in his movies. One notable instance is in the classic 1932 gangster film "Little Caesar," where he played the role of Caesar Enrico Bandello, a ruthless gangster who often refers to his subordinates as "wise guys."
* James Cagney: Cagney, another legendary gangster actor, was also known for using the phrase "wise guy" in his films. In the iconic 1938 movie "Angels with Dirty Faces," he played the role of Rocky Sullivan, a gangster who uses the term to describe his associates and rivals.
* George Raft: Raft, renowned for his charismatic performances in gangster movies, also employed the phrase "wise guy" in his dialogues. One notable example is in the 1932 film "Scarface," where he portrayed the character of Guino Rinaldo, a mobster who often uses the phrase in a condescending manner.
While these are just a few examples, the use of the phrase "wise guy" in old gangster movies became a common trope, helping to shape the portrayal of certain types of characters and the overall atmosphere of these classic films.