In 1931, Gould was hired as a cartoonist with the Chicago Tribune and introduced Dick Tracy in the newspaper The Detroit Mirror on Sunday, October 4, 1931. He drew the comic strip for the next 46 years from his home in Woodstock, Illinois. Gould's stories were rarely pre-planned, since he preferred to improvise stories as he drew them. While fans praised this approach as producing exciting stories, it sometimes created awkward plot developments that were difficult to resolve. In one notorious case, Gould had Tracy in an inescapable deathtrap with a caisson. When Gould depicted Tracy addressing Gould personally and having the cartoonist magically extract him, publisher Joseph Patterson vetoed the sequence and ordered it redrawn.
Late in the period of Gould's control of it, the Tracy strip was widely criticized as too right-wing in character, and as excessively supportive of the police. This commentary argued that Gould was using the strip to push his own political agenda such as attacking the rights of the accused at the expense of storytelling. Additionally, the late 1950s saw a changing newspaper readership that was perhaps less tolerant of Gould's style.
For instance, Gould introduced an odoriferous, chewing tobacco spitting character, B.O. Plenty, with little significant complaint from readers in the 1940s. However, the 1960s introduction of the crooked lawyer Flyface and his relatives, surrounded by swarming flies, created a negative reader reaction strong enough for papers to drop the strip in large numbers. There was then a dramatic change in the strip's paradigm to feature science fiction plot elements with regular visits to the moon. This led to an increasingly fantastic procession of enemies and stories that largely abandoned the strip's format of urban crime drama. The Apollo 11 moon landing prompted Gould to abandon this phase. Finally, Dick Tracy was beset by the overall trend in newspaper comics away from strips with continuing storylines and toward those whose stories are largely resolved within one series of panels.
Gould, his characters and improbable plots were satirized in Al Capp's comic strip Li'l Abner with the Fearless Fosdick sequences (supposedly drawn by "Lester Gooch"); a notable villain was Bomb Face, a gangster whose head was a bomb.
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