Production Set Stills: Fun With Music Day
Sherry watches the photographer as Cubby gets briefed by a crew member on how to use some paint brushes in lieu of drumsticks. This was from a second season Fun with Music Day skit, probably the one called Scribbletown. I have no idea how the storyline went, though I believe it also featured Jimmie and Roy.
The Full Picture
This scene was filmed September 14, 1956, and, if it was from the skit mentioned above, first broadcast February 18, 1957. The crew member in this picture, Jim MacDonald, was the on-stage sound effects man for the show, and was a drummer for the Firehouse 5 + 2 band. He also occasionally provided the voice for Mickey Mouse after Walt Disney stopped doing so. (Thanks to Lonnie Burr for this information).
Though they were often grouped together for performances during the show's run, Cubby and Karen have always maintained they were never a real "couple". In a recent interview with Shokus Internet Radio, however, Cubby seemed to hint that he and Sherry did see each other socially as teenagers.
Set stills like these were made for the property department, and were not intended for release as publicity photos. Most set stills are devoid of cast and crew; the photographer was only concerned with capturing the appearence of the stage and the presence of people in the frame was a matter of indifference. Hence, when they do show up, as above, they are often out of focus and poorly lit.