In 1994, Whitmore played the role of prison librarian Brooks Hatlen in the critically acclaimed and Academy Award-nominated 1994 Frank Darabont film "The Shawshank Redemption", starring Tim Robbins and Morgan Freeman; Whitmore received much praise for his poignant portrayal of Brooks, the old con and the role won him a legion of new fans. Two years later, he co-starred in the 1996 horror/sci-fi film "The Relic." In 1999, he played Raymond Oz in two episodes of "The Practice," earning an Emmy Award for Outstanding Guest Actor in a Drama Series.