After testing the waters as a director with a 1989 episode of tales from the Crypt, Helgeland made his feature directorial debut with the 1999 el Gibson crim thriller Payback taking the full reigns for the medieval popcorn flick A Knight's Tale, the remarkably fun flick not only proved that he could shift gears with the best of them, but also that he could successfully follow through on his vision no matter how outlandish it might seem at conception. The film helped to launch thë career of Heath Ledger, and right around the time of A Knight's Tale release, filmmaker Clint Eastwood was busy shooting Helgeland's adaptation of Michael Connelly's novel Blood Work. Released the following year, Blood Work drew fair reviews, and a creative spark between Eastwood and Helgeland would soon catch fire when the former asked to latter adapt Lahan's Mystic River for the screen. A profound meditation on the cycle of violence which results from an unspeakable crime, Mystic River drew rave reviews when released in 2003 and was heralded by critics as one of the best films of the year. Hoping to get back to his roots, Helgeland penned and directed the religious-themed frightener The Order (also 2003); unfortunately, the film was both critically maligned and a box-office bomb. Helgeland's next screen play, the revenge-themed thriller Man On Fire, would go before the cameras under the direction of Tony Scott for a 2004 release.