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 .