Both Shelley Long and Bette Midler were promised top billing when they signed to do the film. Neither one wanted to give up top billing to the other. So west of the Mississippi River, Long got top billing and Midler got top billing east of the Mississippi.
According to the 80s Movie Rewind, when Bette Midler fell in front of a lorry in the movie, it was not part of the script. Midler had winged it during the shot because she thought it would look good in the film. Shelley Long and the crew were worried about the prat-fall with Long quickly rushing to her aid and pulling Midler to the kerb-side. The scene was kept in the picture.
Reportedly, Bette Midler wanted to do all of her own stunts, which meant falling over and jumping around cliffs during the film's climax, something which was of concern to the production, for both Midler and her baby's health and safety.
The "Outrageous Fortune" title is taken from Act 3, Scene 1, Line 58 of William Shakespeare's play "Hamlet". It's from the start of the famous "To be or not to be" speech which states: "To be, or not to be, that is the question: Whether 'tis nobler in the mind to suffer the slings and arrows of outrageous fortune, or to take arms against a sea of troubles. And by opposing end them". In the movie, Shelley Long's character confesses at the beginning of the movie that she someday hopes to play Hamlet. At the end of the film, Long does, with Bette Midler also in the cast.
The picture is considered to be a female version of a male buddy movie. Halliwells said that the film was "a traditional male buddy film that has substituted women" whilst Movies on TV & Videocassette said that the movie was a "variant on the male buddy-buddy movie". Moreover, Allmovie states that this buddy movie has its "leads essayed by women".
There was a row between who would get top billing on the film. First billing on the film print at both the start and closing credits went to Shelley Long with Bette Midler being second billed. But many of the movie posters and DVD covers have Midler billed first. Midler had previously starred in Touchstone's comedy-smash Ruthless People (1986) whereas Long had similarly starred in the hit-comedy Night Shift (1982). Midler ended up being Golden Globe nominated for Best Performance by an Actress in a Motion Picture Comedy/Musical for her role in Outrageous Fortune (1987), suggesting her performance was the more dominant of the two leads, and thus, getting top billed post-theatrical release on the home-video and DVD covers, with Long having the prime billing still on the film print.
The setting of the cliffhanger finale, at the Four Fingers on the Mesa Azul Cliffs, was both a fictional name and fictional location, the place being apparently just a matte painting. Any real life photography associated with the sequence was done in New Mexico.
Some movie posters for the film featured a long blurb that read: "The CIA is trailing them. The KGB is tracking them. The phone company is tracing them. The police are chasing them. The cowboys are herding them. And the Indians are hunting them. Are they going to fall for all of that?".
The first name of the character of the Russian drama coach, Stanislav Korzenowski, played by Robert Prosky, referenced Konstantin Stanislavski, who was famous for developing the Stanislavski System of Acting.