All recent work has assigned the genera Cheilocephalus Berkey, 1898 and Oligometopus Resser, 1936 to the family Cheilocephalidae Shaw, 1956, a small group of largely Laurentian trilobites from the Late Cambrian Steptoean Stage. New data from Nevada and Newfoundland indicate that the Cheilocephalidae is polyphyletic and that Cheilocephalus and Oligometopus are allied with different superfamilies. The Cheilocephalidae, which includes Cheilocephalus and Pseudokingstonia Palmer, 1965, is assigned to the Dameselloidea Kobayashi, 1935, and a pygidium from the Cow Head Group of Newfoundland indicates that Cheilocephalus first appears in the late Marjuman. The Dameselloidea disappeared on other continents at an extinction interval at the end of the Marjuman, but Cheilocephalus survived and underwent modest diversification in Laurentia in the succeeding Steptoean Stage. Oligometopus is transferred to the leiostegioidean family Leiostegiidae Bradley, 1925. The genus shows closest affinities with such Gondwanan genera as Idamea Whitehouse, 1939, and its appearance in mid-Steptoean strata records immigration of the Leiostegoidea into shelf-margin environments of Laurentia.