The steeply falling jet spectrum induces a bias on the medium modifications of jet observables in heavy-ion collisions. To explore this effect, we develop a novel analytic framework to study the quenched jet spectrum and its cumulative. We include many energy-loss-related effects, such as soft and hard medium induced emissions, broadening, elastic scattering, jet fragmentation, cone size dependence, and coherence effects. We show that different observables, based on the jet spectrum, are connected, e.g., the nuclear modification, spectrum shift, and the quantile procedure. We present the first predictions for the nuclear modification factor and the quantile procedure with cone size dependence. As a concrete example, we compare dijet and boson+jet events to unfold the spectrum bias effects, and improve quark-, and gluon-jet classification using arguments based on the cumulative. Besides pointing out its flexibility, finally, we apply our framework to other energy loss models such as the hybrid weak/strong-coupling approach.