In the late '90s Glenn alternated between mainstream films ("Courage Under Fire" (1996), "Absolute Power" (1997)), independent projects ("Lesser Prophets" (1997) and "Larga distancia" (1998), written by his daughter Dakota Glenn) and TV ("Naked City: A Killer Christmas" (1998)).
V 1990. je njegova poklicna pot doživela višek, saj je zaigral v uspešnicah kot so "Ko jagenjčki obmolknejo" ("The Silence of the Lambs") (1991), "Lov na rdeči oktober" ("The Hunt for Red October") (1990) in "Igralec" ("The Player") (1992).