Outcault began his career as Thomas Edison's technical illustrator and as humoristic sketcher for the magazines Judge and Life, but soon joined Joseph Pulitzer's New York World. Pulitzer used Outcault's comics in an experimental color supplement, using a single-panel color cartoon on the front page called Hogan's Alley, depicting an event in a fictional slum. A character in the panel, The Yellow Kid, gave rise to the phrase "yellow journalism." Hogan's Alley debuted May 5, 1895. The color yellow was picked because it was difficult to print at the time.
In October 1896, Outcault defected to William Randolph Hearst's New York Journal. The result of a lawsuit awarded the title "Hogan's Alley" to the World and "The Yellow Kid" to the Journal.
In 1902, Outcault introduced Buster Brown, a mischievous boy dressed in Little Lord Fauntleroy style, and his dog Tige. The strip and characters were very popular and Outcault eventually licensed the name for a number of consumer products, most notably Buster Brown shoes.
In the Journal, Outcault began experimenting with using multiple panels and speech balloons. Although he was not the first to use either technique, his use of them created the standard by which comics were measured.