Olyphant's first paid acting job was in a 1995 WB television pilot based on 77 Sunset Strip#Legacy. Phyllis Huffman cast him in the role but he did not have an opportunity to meet the show's producer, Clint Eastwood, who quit days before filming began. Later that year, he made his professional Off Broadway debut in the Playwrights Horizons' production of The Monogamist and received the Theatre World Award for Outstanding Debut Performance. He starred in the world premiere of The SantaLand Diaries (1996) at the Atlantic Theater Company, a one-man play based on David Sedaris' essay about working as a Macy's department store Christmas elf. Ben Brantley of The New York Times felt the "charming" Olyphant did "a wonderful job" when imitating other characters but had "a harder time finding a convincing style for the running narrative. " Howard Kissell of The New York Daily News remarked that he delivered "all the drollery with a perfect deadpan and a twinkle" while David Patrick Stearns of USA Today described him as "an excellent young actor who successfully projects the world-weariness of a young 20-something who slowly evolves into somebody who just might believe in Christmas. "