Pruneface's first appears (and dies) in 1942, but the character is revived in 1986; the story explains that he had been reanimated 40 years after his death by the villainous Dr. Cyros Freezedrei. The comic then explains that, prior to his first meeting with Tracy, Pruneface led an espionage ring for the Axis powers to acquire a new secret formula for the deadly Xylon Bomb (capable of blowing up 10 city blocks without the threat of radiation, created by Professor Roloc Bard). The ring consisted of himself (hidden from the readers, going by Boche until halfway through the storyline), Shakey Trembly, Flattop Jones and his gang, and Frieda Smith (the professor's love interest). Forty years later, Pruneface kidnaps the professor and forces him to build the bombs. One is still hidden 10 blocks away from the Oval Office (in an elderly Frieda Smith's basement). Right after she is arrested by Tracy and G-Man Jim Trailer, the bomb is defused. Pruneface then calls her to set it off, causing him and Dr. Freezedrei to change their plans and go into hiding.
He also made a brief appearance in the 1990 film adaptation of Dick Tracy, in which he is portrayed by R.G. Armstrong. In this adaptation, he is an American mobster, operating in Tracy's city, who accepts Big Boy Caprice as his superior. He is eventually gunned down by The Blank.
In Kyle Baker's graphic novels that served as prequels to the movie, Pruneface's real name is given as Lorenzo Prunesti.