This is a still image file of Bob Ross that I found via an internet search. I took it into a separate photo editing software, like Photoshop or Pixlr X, and erased the area where the painting was.
Saving a file as a .png retains its transparency.
This is a video clip of my son, filmed on his webcam. I used the clip editing options in WeVideo to move the frame over and make it slightly smaller to fit in the window of the "painting."
You can see that the Bob Ross image fills the frame. The video of my son will only show through the "window" where I erased the Bob Ross image.