A supporter of modern art during the early years of the twentieth century, Kenneth Hayes Miller believed that the 1913 Armory Show had a tremendous influence on American artists, opening to them myriad expressive possibilities. However, he himself was unaffected by the Cubist and Futurist modes that shocked the viewers in the artistic upheaval of 1913. Miller's own style harks back to the Grand Tradition, to Renaissance order, clarity, volume, and weight. In both his paintings and teaching, Miller strived to bridge the gap between the old masters and the moderns.
Miller also regarded Albert Pinkham Ryder, the single most important influence on his early style (1900-18), as a successor to the Renaissance masters. After seeing Ryder's romantic, visionary canvases during the 1900s, Miller sought out the artist, and a close friendship ensued. He revered Ryder both as a spiritual and an artistic mentor; Ryder, who shunned material possessions to live for his art, embodied the high ethical and moral values that Miller tried to maintain as a religious man. The Portrait of Albert Pinkham Ryder, painted during Ryder's final years, extols the man and his art.
Miller greatly admired Ryder's ability to achieve monumentality in his forms, an effect he captured in this portrait of a dignified and impressive gentleman, portrayed in Ryder's own dark-gray palette and planar modeling technique. The figure is painted with alternating opaque light and transparent dark layers, contrasts that heighten the dramatic tone of the work.
Duncan Phillips began collecting Miller's work in early 1925. Seeing Portrait of Albert Pinkham Ryder in Miller's New York studio in 1926, Phillips appreciated this portrait not only for its intrinsic qualities, but also because it is "a great portrait of a very great man and should be acquired for our Ryder Room." Miller concurred, considering it to be "for external and for implicit reasons probably the most unique piece among all the canvases [I have] done...."