5. ‘Who’s That Girl’
Coming off the back of 1986 flop ‘Shanghai Surprise’ with her then-husband Sean Penn, Madonna returned to the kind of role that won her critical acclaim in ‘Desperately Seeking Susan’. ‘Who’s That Girl’ is a screwball comedy from James Foley, where Madonna played carefree Nikki Finn who gets caught up in a murder. The film didn’t do well at the box office but I always find it fun, mostly thanks to Madonna’s energetic and charismatic performance. It wasn’t a huge stretch for her, but she had fun with the role.