A library of poly(methyl methacrylate)-based dendronized polymers with generation numbers g = 1-3 was prepared, which contain different degrees of dendritic substitution (0-50%) with strongly hydrogen bonding 2-ureido-4[1H]-pyrimidinone (UPy) moieties at their respective g = 1 levels. Our rheological and thermal studies demonstrate that the strong intermolecular UPy interactions are suppressed for g = 2 and essentially eliminated for g = 3. Focusing on samples with short backbone degrees of polymerization (P-n approximate to 40), the linear viscoelastic response alters from liquid-like in the absence of UPy to gel-like with ever increasing moduli as the UPy content increases. Nonlinear rheological measurements indicate a transition from ductile to brittle behavior and, in parallel, a transition from shear strain thinning to shear strain hardening. This unique behavior makes UPy-DPs promising candidates for the design of new functional materials.