The relationships among cypress species of the closely related genera Cupressus L., Callitropsis Oerst., and the recently described Hesperocyparis Bartel & R. A. Price were examined using morphological characters. Previous studies did not fully resolve New World and Old World cypresses, the status of Cupressus duclouxiana B. Hickel, Cupressus benthamii Endl., and Cupressus funebris Endl. being in question. Cupressus duclouxiana is sister to Hesperocyparis and Cupressus benthamii is sister to Callitropsis, while Cupressus funebris is considered a basal taxon to all other Cupressus investigated. The intrusion of Hesperocyparis lusitanica (Mill.) Bartel characters into the standard descriptions of Cupressus torulosa D. Don ex Lamb. is examined in order to clarify the differentiation of the respective genera. An emended description of Callitropsis constituting a grade of three species is provided. The new combination, Callitropsis funebris (Endl.) de Laub. & Husby, is provided for Cupressus funebris. Five names at new varietal rank are transferred to Hesperocyparis, as H. arizonica (Greene) Bartel var. nevadensis (Abrams) de Laub. [≡ Cupressus nevadensis Abrams], H. arizonica var. montana (Wiggins) de Laub. [≡ Cupressus montana Wiggins], H. goveniana (Gordon) Bartel var. abramsiana (C. B. Wolf) de Laub. [≡ Cupressus abramsiana C. B. Wolf], H. goveniana var. pygmaea (Lemmon) de Laub. [≡ Cupressus goveniana Gordon var. pygmaea Lemmon], and H. lusitanica var. lindleyi (Klotzsch ex Endl.) de Laub. [≡ Cupressus lindleyi Klotzch ex Endl.].