After graduating in 1990, Olyphant half-heartedly considered a career in commercial art. While in the process of applying for a master's degree in fine arts and working as a swimming coach at Irvine Novaquatics, Olyphant decided to move to New York to explore other options. He initially performed stand-up comedy: "I'd dabbled and then there was a six-month period where I did it with a certain commitment. Then I'd occasionally go back." Ultimately, he decided to become an actor. In his final year of college, he had taken an acting class as an elective at UC Irvine and found it "really enjoyable". He completed a two-year acting program at New York's William Esper Studio and began auditioning for roles.