By the 1990s, Logan had determined to break into film and had been penning spec scripts. When "Never the Sinner" was revived to acclaim in Chicago—it later was produced off-Broadway in 1997—he utilized the attention as a calling card with movie studios. Asked to come up with ten movie ideas by an agent who liked his plays, Logan offered his idea of King Lear in the NFL. The agent liked the concept and urged the playwright to take a year off from theater work to concentrate on writing it. Turner Pictures purchased his spec script about football, "Any Given Sunday", in 1996 and Oliver Stone signed on as one of the producers. (It eventually ended up at Warner Bros. after the sale of Turner.) "Pure Evel", a biopic of daredevil Evel Knievel also attracted attention and it appeared that Logan would finally achieve his dream. But film development is a decidedly slow process and Logan's first produced script ended up being the teleplay for the 1996 Fox TV-movie "Tornado!", a predictable disaster flick that capitalized on the success of that year's big-screen hit "Twister". It took three more years before another of his efforts hit the screen, though. Logan followed up in 1999 with another less-than-stellar effort, the entertaining, but unoriginal horror film "Bats", which he also executive produced. By the time of that film's release, Oliver Stone had finally decided to make a film set in the world of professional football, combining three scripts owned by Warner Bros., one of which was Logan's. The director worked with Logan (who shared screen credit) and the finished film, starring Al Pacino and Cameron Diaz, earned respectable reviews.
Logan next landed an interview with director-producer Ridley Scott, who was developing a film about the making of "Citizen Kane", a project Logan desperately wanted to be a part of. A long-time history buff, the writer enjoyed researching Orson Welles and his legendary motion picture, and wowed the skeptical Scott with his knowledge of and interest in the subject matter. Scott hired Logan on the spot to write the script for what would become the critically acclaimed, multiple Emmy-nominated HBO drama "RKO 281". When Scott moved on to make an epic set in ancient Rome, he tapped Logan to pen the story for that movie, too, resulting in the second Logan-Scott collaboration, the Oscar-winning "Gladiator". Tapping his love of history, Logan helped craft an appealing and often powerful story—aided by Scott's eye-popping visuals—around the Roman soldier-turned-gladiator Maximus (Russell Crow) and shared and Academy Award nomination for Best Original Screenplay. Demonstrating his love for the fantastic, Logan next adapted H.G. Wells' enduring sci-fi tale "The Time Machine" (2002) for the screen, with less successful results. Hampered by an uneven storyline and a director who was replaced in the 11th hour, the film had some strong individual sequences but failed to gel creatively or commercially.
As a devout fan of every incarnation of "Star Trek," Logan leapt at the chance to pen the screenplay for the tenth feature film, "Star Trek: Nemesis," introduced to the production team by his friend and franchise star Brent Spiner after he and Spiner cooked up a storyline for Spiner's android alter ego Data. The producers eagerly signed on the Academy Award nominee to add fresh blood to Paramount's venerable tent pole property. Logan's screenplay showed heavy influences from "Star Trek II: The Wrath of Khan" and took a darker tone. Despite some missed opportunities, retreaded themes and several deleted scenes, the film was received well by critics and hardcore followers of the franchise but failed to go to warp speed at the box office, grossing slightly more than $40 million (an all-time "Trek" low). Logan rebounded with “The Last Samurai” (2003), an epic adventure about an army captain (Tom Cruise) sent to Japan to train its soldiers, only to be captured by the last remaining Samurais. The captain comes to learn, appreciate then adopt their ways, and eventually leads them into battle against the Japanese soldiers he once trained. The writer then worked with Martin Scorsese on the director’s ambitious biography about maverick tycoon Howard Hughes, “The Aviator” (2004). Broad and sweeping in scope, the film earned many critical kudos and award nominations, including a second Oscar nod for Logan for Best Original Screenplay.