Charismatic Hypselosomatinae (currently 14 extant and fossil genera; 72 species), the “big-eyed minute litter bugs”, are characterized among Schizopteridae (Dipsocoromorpha) by the large eyes, four-segmented labium, and distinctive wing venation. A recent molecular phylogenetic analysis confirmed the monophyly of Hypselosomatinae that were recovered as the sister taxon to the Ogeriinae + Schizopterinae (Weirauch and Štys 2014). Hypselosomatinae occur in the Old and New Worlds, but described species diversity is biased towards the Oriental and Australian regions: only three monotypic genera are currently known from the New World (Glyptocombus Heidemann, Ommatides Uhler, and Williamsocoris Carpintero & Dellapé). Based on 28 male, female, and juvenile specimens from Cuba and the Dominican Republic and a single male specimen from Brazil we here describe two new monotypic genera of Hypselosomatinae, Hypselosomops
pecki
gen. n. and sp. n., and Hypsohapsis
takiyae
gen. n. and sp. n. We provide habitus images, digital illustrations (light, scanning electron, and/or confocal microscope) of wing and male genitalic structures, line drawings of genitalic structures, and distribution maps. Bizarre morphologies, a worldwide distribution with small endemic species ranges, and a fossil record that dates back to the mid-Cretaceous make the Hypselosomatinae a fascinating group to explore in an effort to understand the evolutionary history of Dipsocoromorpha.