Adding to his acting resume, Macht moved into producing with the indie film "Not for Nothin'" (1999, in which he co-starred) and "The Bookie's Lament" (lensed 1999, in which he had a leading role). As the new millennium dawned, his profile rose higher, first with the regular role of the empathetic medical intern in the supernatural series "The Others" (NBC, 2000) and then as actor William Holden opposite Jennifer Love Hewitt in the ABC biopic "The Audrey Hepburn Story" (also 2000). Macht's big screen breakthrough came when he was cast as the well-read and calm Frank James to Colin Farrell's more volatile Jesse James in the revisionist "American Outlaws" (2001). While many critics dismissed the film's anachronistic screenplay, they could not overlook Macht's charismatic screen presence. The rising star next joined Gene Hackman and Owen Wilson in the war drama "Behind Enemy Lines" (2001) before landing a supporting role in "Bad Company" (2002), featuring Chris Rock and Sir Anthony Hopkins.