Madden made his feature directorial debut with "Ethan Frome" (1993), adapted from the Edith Wharton novel, starring Liam Neeson and Patricia Arquette. Though lauded for its fidelity to the novel and its austere snowbound locations, the film seemed emotionally muted to many. Madden followed up with "Golden Gate" (1994), starring Matt Dillon and Joan Chen, directing a highly touted script from playwright David Henry Hwang, but despite the considerable pedigrees of all involved, the film received lukewarm reviews. He scored a critical hit with his best film to date, "(Her Majesty) Mrs. Brown" (1997), based on the relationship of England's Queen Victoria (played by Judi Dench) and a Scotsman (Billy Connolly). "Shakespeare in Love" (1998) reunited Madden with Dench as Queen Elizabeth I, and co-starred Oscar-winner Geoffrey Rush, Ben Affleck and Gwyneth Paltrow. A terrific comedy-drama whose script drew parallels between a fictionalized romance between the Bard and a noblewoman and his play "Romeo and Juliet", "Shakespeare in Love" delighted audiences and critics and received a near-record 13 Oscar nominations including one for Madden as Best Director.
After his Oscar triumph Madden experienced a sterotypical slump with his next effort, an adaptation of the popular wartime romance novel "Captain Corelli's Mandolin" (2001), a less than convincing effort starring Nicolas Cage and Penelope Cruz as an Italian-American solider and a Greek villager, respectively, who fall in love against the backdrop of of a small Greek island in the waning days of World War II. Madden replaced the film's first helmer, the ailing Roger Michell, which may have accounted for the lack of his usual attention to casting, ambience and detail. Madden reteamed with Paltrow to stage a well-received 2002 stage production of David Auburn's Pultizer Prize-winning play "Proof" at London's Donmar Warehouse, but initially balked when approached to helm a film version, fearing that the enclosed world of the theatrical play would be difficult to translate into a movie. After brainstorming several ways to open up the story, the director reconsidered, however, and recruited Paltrow, Anthony Hopkins, Hope Davis and Jake Gyllenhaal for the impressive and critically admired 2005 film, which cast Paltrow as the troubled young daughter and caretaker of a brilliant but schizophrenic mathematician whose death leaves her disturbed that she's inherited his madness and not his genius.