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Yours is a very good question! I can tell you the reason why Keye Luke was not paired with Sidney Toler when the latter took over the Charlie Chan role with the passing of Warner Oland. Simply put, Twentieth Century-Fox and Keye Luke had a contract dispute. From what I have read, Fox was offering Keye Luke considerably less money than he had been making while working with Mr. Oland. Perhaps this was because the studio was unsure as to how the series would fly with a new actor in the lead role.
Interestingly, "CHARLIE CHAN IN HONOLULU" was originally scripted for Warner Oland and Keye Luke and was to have been Oland's first film following his abrupt departure from the set of "CHARLIE CHAN AT THE RINGSIDE." As you mention, "RINGSIDE" was, by salvaging as much shot footage as possible, retooled into a Mr. Moto movie ("MR. MOTO'S GAMBLE"). This film retained most of the original cast, including Keye Luke who played number one son, Lee.
One more titbit regarding "HONOLULU" can be found, I believe, in the film "MR. MOTO TAKES A CHANCE" (please correct me, anyone if I am wrong!), if one looks VERY quickly and closely! It is a poster advertising "CHARLIE CHAN IN HONOLULU" starring WARNER OLAND.
Now, as for why Keye Luke was not featured in the Charlie Chan series when it was taken over by Monogram Pictures. This probably has something to do with the actor being busy working on other projects. During the years of World War II, there was a demand for Asian actors and actresses to play Japanese in the war movies of the time. Looking at Mr. Luke's film list from those years, it can be seen that he was busy making those types of pictures. Following the war, this genre of film decreased rapidly, and we can see that by the time Keye Luke returned to the Charlie Chan series (for the final two films of "same") that his film work had slowed considerably.
If I may add my humble opinion to the mix. If you seen the Oland films with Keye in them, you will notice a very strong chemistry between the two actors. Almost as if Father and Son in real life! To me, a new actor in the role of Charlie Chan called for a different offspring, thereby different actor (or actress as in a couple of the Monogram films). The way Toler portrayed Chan with a more acid-like tongue, called for a son who got into trouble a little more often. Like "Reno" for example. For Charlie to see his own son in a police line-up! Lee, being the oldest, was a little more on the responsible side...I did say "little more" but you see what I mean.
Roland Winters, on the other hand, seemed a mix of Oland and Toler's Chans with his own to boot which I think worked well to have Lee return. You will notice in "Sky Dragon" our film on the 30th a similar kinship he had with Warner Oland but doesn't seem quite as close. Perhaps if Winters and Luke were allowed to continue, as I've read somewhere they were planning many more films, I believe the bond would have been a good one and even allowed Winters to be appreciated more as Charlie Chan.
It has occured to me that from a career perspective Keye Luke may have been better off not doing the post Oland Chan films.
By playing in a variety of other pictures he got wider exposure than he would have otherwise and probably honed his acting skills even more. As a result he was able to make a comfortable living as a character actor well into his 80s.
Sen Yung, by contrast, never enjoyed that kind of career success post Chan even taking his Bonanza years into account.
You actually can see Sidney Toler & Keye Luke acting
together in "The Adventures Of Smilin Jack" A very
good serial from Universal....I believe made in late
1942 or early 43....It's the only known pairing of the two actors to my knowledge...highly recommened