Glackens' friend Everett Shinn contends that "William J. Glackens is the greatest draughtsman this country has produced. I know of no other American artist who has equalled his extraordinary ability as an interpreter of contemporary life."
Born in Philadelphia and educated at Central High School there, Glackens began his career in 1901 as an artist-reporter and illustrator on the staff of the Philadelphia Record before moving to the Press, where he met John Sloan, George Luks, and Everett Shinn, all of whom would join him in the 1908 exhibition that established the group called The Eight or, more derogatively, the Ashcan School. The newspaper job allowed Glackens to finance night classes at the Pennsylvania Academy of the Fine Arts, the only formal training he received. Inspired by Robert Henri, mentor to a generation of painters, Glackens soon focused his interest primarily on painting, and with Henri's encouragement he set forth on a cattle boat to France, where he lived for more than a year, traveling, painting, and studiously avoiding the academies.
Upon his return to America, the young artist took up residence in New York and began to draw magazine illustrations. It was at this time that the group who would become The Eight coalesced, united by a commitment to depict life without sentimentalizing or prettifying it. From the beginning, with the first exhibitions of 1901, Glackens's rare quality of observation and his lively transcription were noted by the critics, and their favorable comments encouraged the modest artist, who, four years later, won honorable mention at the 1905 Carnegie International exhibition with his famous work At Mouquin's, now in The Art Institute of Chicago. Glackens finally renounced illustration altogether and devoted himself to painting, eventually working in an Impressionist style reminiscent of Renoir. Heavily influenced by the French painters, he purchased their work for his friend and fellow baseball enthusiast Albert Barnes, whose foundation in Merion, Pennsylvania, became one of the great repositories of French nineteenth-century art in America.
Given the quality and interest of his drawings, as well as the often positive response to Glackens's newspaper and magazine work, it is, as his son Ira remarked, "hard to believe that [Glackens] hated to do illustrations—which was the sad fact." There is no doubt, though, that his experience in illustration served him well for his painting, since it fostered his lightning scrutiny of an event and developed his skill at instantaneous transcription or the uncannily accurate retention of details that he could reproduce later at the office. Shinn noted that Glackens always "found his subjects in the teeming, sprawling Metropolitan populace" and affirmed that, "If historians of the future wish to know what America of the city streets was like at the turn of the century, they have only to look at these drawings." Glackens's fascination with real life never waned, and he leveled a penetrating eye on the people who passed by the window of his Washington Square studio, making quick sketches that he would then incorporate into finished works.