Darabont crafted his most ambitious, adult work to date adapting another Stephen King work, the novella "Rita Hayworth and the Shawshank Redemption". (The feature's title was shortened to "The Shawshank Redemption") Offered a healthy $2.4 million for his adaptation, he held out for the chance to direct--the result was a critically praised prison story about an unusual but powerful friendship between a level-headed banker convicted of murdering his wife and a seasoned lifer with a knack for acquisitions. The film earned seven Oscar nominations including Best Picture, and for his efforts, Darabont earned nominations from the Directors Guild, the Writers Guild and the Academy (for Best Adapted Screenplay).

Despite several projects in development, it took four years before his next film reached theaters. Darabont reportedly assisted on the screenplay for the WWII drama "Saving Private Ryan" (1998) for director Steven Spielberg, but final screen credit went to writer Robert Rodat. He returned to the director's chair to undertake the screen adaptation of another Stephen King opus, "The Green Mile" (1999), starring Tom Hanks and relative newcomer Michael Clark Duncan. Set on death row in a Louisiana prison in the 1930s, the film focused one particular prisoner with seemingly miraculous powers (Duncan) and his relationship with the other inmates as well as the senior guard (Hanks). Darabont once again proved to be the perfect adapter for King's work, crafting a script that was entirely faithful to the original. His direction stressed the relationships in the film and allowed each actor (including David Morse, Doug Hutchison, Michael Jeter and Sam Rockwell) to contribute solid performances.