This was a interesting and quick way to start off my 8th grade class. My students love to look at music throughout history, and this was a memorable one for them. I particularly like these type of activities as well because they're quick, and draw upon students ELA skills.
The historical analysis part of this activity involves students reviewing the lyrics to answer questions regarding conditions during the Great Depression for the average citizen. In class students either watched the below video, or annotated the lyrics the first time they listened, and the second time they answered the five questions.
I had student listen to this link, where it shows images of Hooverviles while Bing Crosby sings. https://www.youtube.com/watch?v=ISniZI_H7mE