I think the head is the party photo head, just darkened.
It seems like the Hawaiian attire haoles and Orientals are from one event, and the squatting guys and black sailors are from another event, and they are all stuffed together incongruously with a stuffed in Stanley and a pretend 0bama Sr.
What I am wondering is who made this collage and when did it first appear? What did it purport to be? If it was put together as it appears to have been, it was done for a specific purpose.
Yes, understanding the purpose would certainly help, but we do not know the source of the image. It has always been identified as a graduation event - suggesting a farewell/departure from Hawaii.
I suppose all it is useful for is to test our powers of observation.