Anise (Pimpinella anisum L.) is a spice, an essential oil crop, and a medicinal plant with a long history of use. Anise seed oil is extracted from anise seed through steam distillation. There is no experimentally established optimal time for distillation of anise seed. We hypothesized that the distillation time (DT) can be customized for optimum yield and composition of anise essential oil. In this study, we determined the effect of nine steam DTs (5, 15, 30, 60, 120, 180, 240, 360, and 480 minutes) on essential oil yield and essential oil composition of anise seed. We developed regression models to predict essential oil yield, the concentration of individual constituents, and the yield of these constituents as a function of DT. Highest essential oil yield (2.0 g/100 g seed, 2%) was obtained at 360-minute DT. The concentration of transanethole, the major anise oil constituent, varied from 93.5% to 96.2% (as a percent of the total oil) and generally was high at 15- to 60-minute DT and low at 240- to 480-minute DT. However, the yield of transanethole (calculated from the essential oil yield and the concentration of transanethole in the oil) increased with increasing DT to reach maximum at 360-minute DT. The concentration of the other oil constituents varied significantly depending on the DT, and some of them were higher at the shorter DT than at the longer DT. However, the yields of these constituents were highest at longer DT (either 360 or 480 minutes). DT can be used to obtain anise essential oil with different composition that would benefit the essential oil industry. This study demonstrated the need for providing DT in reports where anise seed essential oil yield and composition are discussed. This article can also be used as a reference point for comparing studies in which different DTs were used to extract essential oil from anise seed.