After the success of Purple Rain made Prince a household name, an Oscar and a Grammy winning artist, he was on top of the world. He was always an artist with big ambitions, but once he proved he could actually substantiate them, it became hard to tell him otherwise. This is precisely why Under The Cherry Moon exists. Prince wanted to make another movie, and nobody could tell him "no."
Unlike Purple Rain, which was made largely with a crew of professional filmmakers, his second theatrical film, Under The Cherry Moon, was a largely solo undertaking. Numerous cast and crew changes left Prince himself directing the film, and the script went through numerous rewrites during production.
When it was released, Under The Cherry Moon was critically panned. It won multiple awards at the infamous Golden Raspberries, including Worst Picture, Worst Actor (Prince), Worst New Star (Kristin Scott Thomas), and more. People, for one reason or another, expected a sequel to Purple Rain. Had anyone been paying attention, they should have known better when the follow-up album, Around The World In A Day, was a drastic departure.
As a result, Under The Cherry Moon has all but faded into the mists of obscurity and become one of Prince's biggest failures, but I say it's an underrated and grossly misunderstood film. As a lifelong Prince fan, I consider it his best film - at least for pure entertainment value - and a fascinating look into a side of Prince people seldom saw - his humorous side.