Harold Kerr Eby was born in Tokyo, Japan where his father was serving as a missionary for the Canadian Methodist Church. At the age of 18, Eby moved to New York to attend the Pratt Institute. He later studied with George Bellows at the Art Students League. A frequent visitor to the Cos Cob artist colony in Connecticut, Eby became friends with the older Childe Hassam. Hassam had previously tried his hand at etching but his plates remained unfinished until he received lessons in etching from Eby.

In 1917, Eby enlisted in the United States Army where he served in a medical unit. He translated his own war experiences into drawings and prints depicting the horrors of war. He was a member of the Century Club and the National Academy of Design. Upon his death, Eby's prints were acquired by the Metropolitan Museum of Art.