Description from Wikipedia:
Under the Cherry Moon is a 1986 American musical drama film directed by and starring Prince as a gigolo named Christopher Tracy and Time member Jerome Benton as his partner, Tricky. Together, the pair swindle wealthy Frenchwomen. The situation gets complicated when Christopher falls in love with heiress Mary Sharon (Kristin Scott Thomas) after planning to swindle her when he finds out that she receives a $50 million trust fund on her 21st birthday. Mary’s father Isaac (Steven Berkoff) disapproves of the romance and provides an excellent adversary for Tracy. The film was Prince’s first film as a director.