After enrolling at the Playhouse West acting school in Los Angeles, Caan began acting in the late 1990s, appearing in a number of independent films and low-budget films.
Nakon što je upisao školu glume Playhouse West u Los Angelesu, Caan je započeo glumačku karijeru u kasnim devedesetima prošlog stoljeća, glumeći u raznim nezavisnim i niskobudžetnim filmovima.