Ok given Madonna is 50 I've selected her first film, the film along with her fledgling music career at this point (1985) that sealed her forever in our radar.
I've nabbed a brief synopsis to remind you of the plot -'Taken-for-granted housewife Roberta passes the time following the progress of Susan who regularly contacts her boyfriend Jim through the Personals. When she sees the two are meeting in New York Roberta goes along, ending up buying Susan's coat. Finding a locker key in the pocket she in turn advertises for a meeting with Susan. Jim sends his projectionist pal along to see what is going on, and when Roberta knocks herself out he assumes she is Susan. Then things start to get complicated.'It wasn't a great film and it wasn't a dreadful film. The main departure for this film was the central placing of two female characters - they were the pivotal points and this is notable in itself. Thelma and Lousie in 1991 is again remarkable for its two female leads and what is viewed with as a break from tradition.
The costume designer Santo Loquasto designed Madonna's character Susan's leather pyramid jacket. In reality Madonna was chosen for her sense of style - after Madonna's first screen test, the producers asked her to take four weeks of acting lessons and get screen-tested again. Although the second screen test wasn't much of an improvement, the director still wanted her for the role, for her presence and sense of style more than anything else. Susan Seidalman also directed 3 episodes of Sex and the City in 1998. It was the sense of style and New York that defiend Desperately Seeking Susan. It felt like an indie film even though it wasn't.
Rosanna Arquette actually won a BAFTA for best supporting actress - technically if you count footage and dialogue she was the lead! Madonna hey irrepressible then as now!