'Under the Cherry Moon' (1986)
Prince's movie after Purple Rain was not, alas, its sequel; that dubious honor belongs to 1990's Graffiti Bridge, which sees The Kid and Morris Day's rivalry continue into the next decade. But the Purple One's directorial debut holds the distinction of having the widest disconnect between the watchability (or unwatchability) of a film and the listenability of its soundtrack — in this case, Prince's psychedelic pop-infused album Parade (featuring "Kiss" and "Mountains"). Blame it on the studio heads at Warner Bros., who should have known the movie was headed for disaster when director Mary Lambert — who proudly put her stamp of approval on the lackluster Stephen King adaptation Pet Sematary — departed the project due to creative differences with the music icon. The result was a soundtrack that sold more than two million copies and a wannabe-Felliniesque musical drama that won five Golden Raspberry Awards, including Worst Actor and Director for Prince, and a tie (with Howard the Duck) for Worst Picture.