The topside ionosphere extends from the F2-layer peak, where the electron density reaches its absolute maximum in the ionosphere, to the overlying plasmasphere and magnetosphere. In the topside ionosphere, the electron density decreases with height with a vertical variation rate strongly dependent on height itself. The last version of the International Reference Ionosphere (IRI) model, i.e., IRI-2020, describes this complex behavior through four topside options based on different sub-models (i.e., options) developed from the 1970s to the present. All these options have in common the F2-layer peak as an anchor point, while they differ in their topside electron density profile and/or plasma effective scale height formulations. In this work, we perform a validation of the accuracy of the four IRI-2020 topside options based on the comparison against in-situ electron density observations by Gravity Recovery and Climate Experiment (GRACE), Ionospheric Connection Explorer (ICON), and Defense Meteorological Satellite Program (DMSP) F15 low-Earth-orbit satellites. Datasets used in this study encompass observations recorded from 1999 to 2022, covering different diurnal, seasonal, and solar activity conditions, on a global basis and for the height range 400–850 km above the ground. The nearly two solar cycles dataset facilitated the evaluation of IRI-2020 topside options ability to reproduce the spatial and time variations of the topside ionosphere for different solar activity conditions. The weaknesses and strengths of each IRI-2020 topside option are highlighted and discussed, and suggestions on how to improve the modeling of the challenging topside ionosphere region within the IRI model are provided for future reference.