Author Existence Failure - Three times. Rick Fletcher, who replaced Chester Gould as artist, died in 1983, and writer Mike Kilian died in 2005. Probably the most tragic instance came in 1986 with the premature death of John Locher, who was in the process of taking over the strip's art duties from his father.
Creator Breakdown - Gould actually thought turning a strip about an urban cop into a science fiction series on the moon was a good idea. Then again, given the sheer volume of contempt Gould had towards various 1960s Supreme Court rulings regarding due process rights all criminals have, Gould probably thought turning the book into a sci-fi strip would be better for his mental health.
Judging by the decline of the strip's artwork quality from 2006 to 2011, some fans consider Dick Locher to have suffered one of these, most likely because he experienced both the death of both his son (John Locher, who was co-artist in the mid-80s) and one of his closest friends (Mike Kilian, who was the writer between 1992 and 2006) while working on the strip.
Executive Veto: Dick Tracy had such a moment when the creator, Chester Gould, put Dick in a truly inescapable Death Trap. Gould was so stumped for a solution that he decided to have Tracy Break The Fourth Wall and address Gould himself who literally extends his hand to lift the Detective out. His publisher, Joseph Patterson, rightly concluded that this was an dumb idea and ordered Gould to redraw the section into something, anything, else.
Keep Circulating the Tapes: Sadly, collections of the various Dick Tracy comic strips are few in number and those few that DO exist, largely focus on the early 1930s era. In particular, Max Collins' critically acclaimed run on the strip has only had three printed volumes, though some of his strips appeared in other collections.
This is becoming a subverted trope, as since 2006, IDW has been publishing the "Complete Chester Gould's Dick Tracy". Fifteen volumes (covering the start of the strip in 1931 to Late-October 1954) have been released. The intent is to produce the series until the entire Gould Run (up to December 1977) has been covered.
Sadly, though, these strip volumes keep going out of print and the prices on Amazon and other such sites go up drastically. However, they bring back these strip volumes eventually. Sorry for anyone who wants to read the Flattop and Brow sagas!
Also, you can probably pick up some of those little issues of the Dick Tracy comic books, which are actually the Dick Tracy comic strips in a compressed, Comic Book styled format.
Trailers Always Spoil: Overlaps with The Merch. In 1990, Playmates Toys released an action figure line to coincide with the movie. "The Blank" was a Canada-exclusive figure and if you pulled off the blank-mask, you revealed Madonna's face underneath.
Development Hell: The film switched studios, writers, and directors multiple times, especially since Beatty refused to make the film realistic and gritty, and eventually helmed the film himself. Beatty hoped to make a sequel, but Disney had no interest after the film didn't pull the kind of numbers Batman did despite an all-out marketing blitz. The film rights to the property have been in legal battle for the last twenty years as Beatty and The Tribune Co. have continued to try to stake their claim to it, with Beatty finally winning in March 2011. He hopes to finally make a follow-up to the film, but has not indicated when he would begin pre-production or a script.
Tim Burton was offered to direct it at one point but had to turn it down to focus on Edward Scissorhands.
Brooke Shields almost secured the role of Breathless, but was changed nearly last-minute because producers thought she was too young for the role.
Danny Elfman originally proposed a darker, more Gershwin-inspired score that was very different from the one heard in the movie proper. He later released it on Volume 1 of his compilation album, Music for a Darkened Theater.