26. Who's That Girl (1987)
Director: James Foley
Stars: Madonna, Griffin Dunne, Haviland Morris, John McMartin
Lame Love Song: "What the World Needs Now is Love," Burt Bacharach
Love Conquers: Parole
Who's That Girl seemed destined to fail from the beginning. After the abysmal Shanghai Surprise, Warner Bros. wanted assurances that Madonna was "ready" to be a leading lady. Turns out she wasn't. (Nor has she ever cracked actor-musician double threat status.)
Granted, she wasn't helped by the plot, which featured a parolee falling in love with her tax attorney and scenes with a live cougar. But Madonna's indulgence in the worst of vanity vehicle clichĂ©s, like refusing to do more than one take, certainly couldn't have helped.