By 1932, the Reiss calendars used a design of simple geometric shapes. I believe that Winold Reiss himself designed the background. Note that the letters are each individually drawn to fit in the space available.
Click image to download a 1.6-MB PDF of this calendar. The PDF includes the calendar portion that is omitted from the above image.
This painting of Arrow Top was also in the 1940 portfolio. The Blackfeet geneology tells us that Arrow Top was born in 1862 to parents named Old Man and Blanket Woman. When he was 24, he married an 11-year-old girl named Squirrel. They are listed as having twelve children, at least one of whom died in infancy. Since most of the paintings Louis Hill bought from Reiss were painted in 1927 and 1928, Arrow Top was probably about 65 when this painting was made.