Format: Amazon Watch Party
Director: James Foley
I don't know what the opposite is of "catching lightning in a bottle", but Who's That Girl? (1987) is here to make me wonder what that might be, or if we're in need of a new phrase.
Look. If you were a straight dude coming of age in the 1980's, you might not have talked about it, but chances are you spent a lot of time thinking about Madonna. Not as part of the cultural discourse that somehow always placed Madonna in the middle of the po-discourse Venn Diagram and which was mostly nonsense, but for other reasons. There's twenty seconds of video here which will help you understand.
So, yes. Madonna. By 1987 she was a marketing and musical force who decided to dabble in acting. Warner Bros., who was in the Madonna business and made both music and movies, said "sure, whatever". Madonna somehow landed on a script about a girl getting out of prison who has to prove she's innocent, and decided this would be the movie she'd make.
If catching lightning in a bottle is an unique combination of factors that come together and create a very special film, this is a mix of predictable hackery paired with an unprepared celebrity who doesn't know the difference between fame and talent needed to pull off a project.