Accreting supermassive black holes frequently power jets that interact with the interstellar medium (ISM)/circumgalactic medium, regulating star formation in the galaxy. Highly supersonic jets launched by active galactic nuclei (AGN) power a cocoon that confines them and shocks the ambient medium. We build on the models of narrow conical jets interacting with a smooth ambient medium, including the effect of dense clouds, which are an essential ingredient of a multiphase ISM. The key physical ingredient of this model is that the clouds along the supersonic jet beam strongly decelerate the jet head but the subsonic cocoon easily moves around the clouds without much resistance. We propose scalings for important physical quantities—cocoon pressure, head and cocoon speed, and jet radius. For the first time, we obtain the analytic condition on the ambient medium’s clumpiness for the jet to dissipate within the cocoon and verify it with numerical simulations of conical jets interacting with a uniform ISM with embedded spherical clouds. A jet is defined to be dissipated when the cocoon speed exceeds the speed of the jet head. We compare our models with more sophisticated numerical simulations and direct observations of jet–ISM interaction (e.g., quasar J1316+1753), and we discuss implications for the Fermi/eROSITA bubbles. Our work also motivates effective subgrid models for AGN jet feedback in a clumpy ISM unresolved by the present generation of cosmological galaxy formation simulations.