Some time ago, I ran into a reference on pages 67-68 of James L. Neibaur’s The Andy Clyde Columbia Comedies noting Ray in the cast of the 1937 Andy Clyde short, “He Done His Duty”.
Through the generosity of a film collector, I was finally able to view the short and confirmed that, indeed, Ray appears in the film.
Neibaur describes the plot of the film:
This was the third and final Andy Clyde comedy in which he plays the sheriff and Robert McKenzie portrays fire chief Cy Ruggles in the town of Mooneyville. The object of their affection, Ivy Flowers, swindled Ruggles and left town in the previous film Stuck in the Sticks, so in this one there are new conflicts. First, Cy decides to run for sheriff against Andy. Then Kitty, a younger, prettier female swindler, stops in town posing as a federal investigator. Andy and Cy’s rivalry for a woman is again rekindled-and Cy is swindled out of another $1000.
In “He Done His Duty”, Ray appears about half-way through in a wanted poster – it turns out Ivy Flowers is Ray, playing a female impersonator con artist.

In the second half of the short, after Kitty swindles Andy and Cy, she takes off in her car with her co-conspirator, Jack Parker (Ray) and a chase ensues.

I’m going to continue investigating this series of films. Even though Ray isn’t mentioned in the cast of the previous entry and Ivy Flowers could have been played by a different actor or actress, I’d like to verify if he plays Ivy in the prequel to “He Done His Duty”.
I looked it up on IMDB and apparently in the prior film, Stuck in the Sticks (earlier the same year, 1937) Esther Howard, a really good middle-aged character actress who I remember best for “Born to Kill” with Lawrence Tierney, Claire Trevor and Elisha Cook, Jr., played the Ivy Flowers character and not Ray.
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