I'll enter too.
I chose a very important man.
Here's to you, Chief Sitting Bull:
I do not know in which year this particular picture was taken, it was certainly in the 19th century since he died in 1890.
According to this
(PDF document - look for image 09i) the original photo was taken in August 1885 by Montreal photographers William Notman & Son. The feathers were later (in 1904?) added or retouched by F.A. Rinehart of Omaha. Some of these details can be made out from writing on the uncropped image