Gould's stories were rarely extensively preplanned as he preferred to improvise his stories as he drew them. While fans praised this style as creating exciting stories, it sometimes created awkward plot developments that were difficult to resolve. A notorious case was when Gould had Tracy in an inescapable deathtrap in a caisson. Gould first depicted Tracy addressing Gould personally and having the cartoonist magically extract him. It was a move that his publisher, Joseph Patterson, personally vetoed and ordered a redraw of the sequence.
Gould visited the workshop of an engineer friend named Al Gross who invented the walkie-talkie, a portable two-way radio and the pager. Gross was working on a wrist-watch version of the two-way radio which he showed to Gould. Gould asked Al Gross if he could use this concept in his Dick Tracy comic strip. Gross said yes and in January 1946, Dick Tracy started wearing the wrist radio. Gould created a cartoon character named Brilliant, an engineer who worked for a company run by cartoon character Diet Smith. Brilliant was modeled after Al Gross. Whenever Gould needed a futuristic invention that his cartoon characters could use, Al Gross would give him ideas such as the video security camera, handheld video camera, and wrist video camera.
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 right-wing 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 grotesque style. Whereas in the 1940s when Gould introduced an odoriferous, chewing tobacco spitting character, B.O. Plenty, with little significant complaint from readers; the later introduction of the crooked lawyer named "Flyface" and his relatives, all of whom were surrounded by swarming flies at all times, 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 story lines and toward those whose stories are largely resolved within one series of panels.
Gould, his characters and improbable plots were satirized in the Fearless Fosdick sequences (supposedly drawn by "Lester Gooch") appearing within Al Capp's comic strip Li'l Abner; a notable villain was Bomb Face, a gangster whose head was a bomb.
Gould retired December 25, 1977 and died May 11, 1985 of congestive heart failure. His life and creations are memorialized in the Chester Gould-Dick Tracy Museum in Woodstock, Illinois.