Softley truly broke out with Hossein Amini's adaptation of the Henry James story "The Wings of the Dove" (1997). His strong pop-culture links caused him to initially shy away from the psychologically complex work of James as "user-unfriendly for adaptation," but he became intrigued by analogies between the plot and the conventions of film noir stories, learning with interest that hard-boiled detective writer Dashiell Hammett had named James among his favorite authors. The fact that the film's denouement takes place in Venice, a city he had visited and painted as a student, clinched the deal for him. As he became immersed in it, Softley recognized "The Wings of the Dove" as a rites-of-passage story too, its love triangle similar to the one at the core of "Backbeat," and ended up directing the handsome costume drama with surprising feeling and empathy.
Four years after “The Wings of the Dove,” Softley ventured into science fiction fantasy with “K-PAX” (2001), a well-intentioned, but ultimately saccharine tale about a mental patient (Kevin Spacey) claiming to be an extraterrestrial from the utopian planet of K-PAX. His psychiatrist (Jeff Bridges) tries to cure him of the apparent psychosis, but soon begins doubting his diagnosis and science in general. Though promising deep insight into human nature through its alien protagonist, “K-PAX” left audiences wanting. Another four years passed before Softley released another movie. The versatile director switched gears to helm a supernatural thriller, “The Skeleton Key” (2005), starring Kate Hudson, Gena Rowlands and John Hurt. In the murky bayous of New Orleans, a young hospice worker (Hudson) finds work as the caretaker of the owner of an isolated plantation rumored to be steeped in the mystical forces of voodoo and black magic. But the forces of evil trapped behind an attic door are unleashed, forcing the hospice worker and her patient to flee for their lives.