The character of Charlie Chan was created by author Earl Derr Biggers, who wrote several mystery novels featuring the character. Biggers based Charlie Chan in part on a Honolulu police officer named Chang Apana. Both the character of Charlie Chan and the real-life Chang Apana worked in Honululu and were accomplished, respected police officers of Chinese descent, but the similarities seem to end there. The first screen appearances of Charlie Chan were in silent serials and the character also had a small role in the 1929 early talkie "Behind That Curtain."
In 1931, Fox studios cast Warner Oland as Charlie Chan, who had previous experience playing Asian roles. For the most part, Warner Oland played Chan as a soft-spoken, polite detective, an aspect that was noticeably different from Earl Derr Biggers' original, more assertive Charlie Chan. However, Chan's wise proverbs and powers of deduction remained much the same in the films as they were in the novels. Warner Oland had a very successful run as Charlie Chan from 1931-37, and starred in perhaps the most acclaimed Chan film, "Charlie Chan at the Opera," co-starring Boris Karloff. The character of Chan was unique; he had no trouble coming up with wise proverbs or sayings for any situation. An example of one of his sayings- "Politeness is the golden key that opens many doors." He was often underestimated, even by members of the police force, and always came out ahead, no matter what people thought of him. This was a step forward for people of Chinese descent, because there had previously never been a Chinese character in movies that was not a villain or a negative stereotype. Warner Oland visited Shanghai, and was thought by many to really be Chinese, a testament to his believability in the role of Charlie Chan. One of the elements that made the series so popular was the addition of Charlie Chan's enthusiastic Americanized sons, played mainly by Asian actors Keye Luke, Sen Yung, and Benson Fong. Their amateur detective work and comedic chemistry with their onscreen "dad" was a key addition to the films' success.
Warner Oland died suddenly of pneumonia in 1938, and there was uncertainty whether or not the role of Chan could be re-cast. The Charlie Chan film series was very popular for 20th Century Fox, so they decided to continue with the series and cast Sidney Toler as Chan. Toler played Chan more assertively than Warner Oland had and was a hit with fans of the series, continuing the Fox films successfully until 1942. 20th Century Fox dropped the film series, but Sidney Toler, who gained the screen rights to the character of Charlie Chan from Earl Derr Biggers' widow, was able to continue in the role of Charlie Chan at Monogram studios, starting with "Charlie Chan in the Secret Service" in 1944. Sidney Toler continued in the role until 1947, when he died of colon cancer (then known as intestinal cancer). Monogram studios still had a successful series on their hands, and they were eager to re-cast Chan. Roland Winters quickly got the role (he was cast even before the studio executives saw the film of his screen test). Although a capable actor, many felt that Roland Winters was miscast as Charlie Chan. He did not really look Chinese and was nearly the same age as Keye Luke, who played his son in the last two Chan films. He played Chan until 1949's "The Sky Dragon," the last film in the series.