Kloves insisted on directing his next screenplay, which led to delays in getting the project greenlighted but resulted in the intriguingly somber drama "The Fabulous Baker Boys" (1989), starring Beau and Jeff Bridges and Michelle Pfeiffer. A moderate success, it demonstrated that Kloves, while not a showy filmmaker, had a flair for set pieces and could make a well-crafted, entertaining film out of deliberately low-keyed plot material. He followed up with another character study, "Flesh and Bone" (1993), a very moody Texas love story starring Dennis Quaid, Meg Ryan, James Caan and Gwyneth Paltrow. Some critics, such as Andrew Sarris, gave it rave notices, but, in general, both the reviews and the box office were uneven. Still the movie featured more interesting elements--and darker character turns--than the average Hollywood fare, so interest in future Klove projects remained high. But instead Kloves dropped out of the industry for several years, inspired by the death of his producer and best friend Mark Rosenberg in November 1992 during the fliming of "Flesh and Bone," as well as the subsequent birth of Kloves' first child. "It was much more entertaining to watch my daughter grow up," he said, "than it was to wait for a 50-year-old movie executive to grow up."

When he was finally ready to return to films, Kloves chose an extremely appropriate vehicle, adapting Michael Chabon's acclaimed novel "Wonder Boys" (2000) into a screenplay--appropriate because the central character Grady Tate (played by Michael Douglas in the film) was a floundering novelist and college professor who, like Kloves, had not delivered any new material for seven years. The resultant adaptation drew rave reviews, was nominated for an Academy Award, Golden Globe and Writers Guild Award (among other honors) and provided Douglas to shake off his movie star aura and tackle a more serious acting role than he had in a recent memory.

Although Kloves entertained plans to return behind the camera, his post-"Wonder Boys" work has continued to focus on adapting popular novels for the big screen. After meeting with British author J.K. Rowling and successfully convincing her he did not plan to unnecessarily Americanize her beloved, bestselling "Harry Potter" series, Kloves earned her blessing and was able to successfully imbue the youth-oriented material with the same sense of character-driven darkness that embodied his other screen works. To date Kloves has penned the screenplays for the series' first four instalments" "Harry Potter and the Sorcerer's Stone" (2001), "Harry Potter and the Chamber of Secrets" (2002), "Harry Potter and the Prisoner of Azkaban" (2004), "Harry Potter and the Goblet of Fire" (lensed 2004) and is signed to write the announced fifth sequel "Harry Potter and the Order of the Phoenix."