Although he made an isolated appearance in the 1978 comedy "Take Down", Miller did not begin acting in earnest in feature films until the late 80s. He had a bit roles in "Out Cold" (1988, as a plumber) and "Three Fugitives" (1989, as a police officer). After "Pretty Woman" (in which his boutique manager was manipulated by Julia Roberts to give up his tie for Richard Gere and to order pizza as she shopped), larger roles followed, including that of the dean of a college with a 34-year old quarterback in "Necessary Roughness" (1991) and an Indian Chief with a Brooklyn accent in the send-up "Carry on Columbus" (1992). Miller was Ray Liotta's composing partner in "Corrina, Corrina" (1994) and in the ensemble cast of "Radioland Murders" (1994). In 1996, he co-starred in "The Nutty Professor", as the dean.
Miller's early work on TV was on shows featuring stand-up comedians, such as "Showtime Funnymen: Triple Clowns of Comedy" and HBO's "One Night Stand" (both 1988). In 1991, Miller played an arrogant college professor in "Frankenstein: The College Years" (Fox), his first TV-movie. In 1992, he starred in his own HBO comedy special, "Larry Miller: Just Words", which was nominated for a CableACE Award. He played the dean of the college with a genius underfoot in "The Computer Wore Tennis Shoes" remake (ABC, 1995). While he had a recurring role as Lou, Paul Reiser's friend and co-worker during the 1993-94 season of NBC's "Mad About You", Miller's first regular role on a series came during the 1995-96 season as the bothersome brother-in-law on "Pursuit of Happiness" (NBC). When that show flopped, he moved on to co-star on the sitcom "Life's Work" (ABC, 1996-97). During the 1994-95 season he portrayed a nightclub owner who was tried and acquitted of murdering his wife on "Law & Order", although the audience was left the impression that he had gotten away with the dastardly deed. During the 1995-96 season, Miller was brought back for another episode, again accused of murdering his wife. This time, he was captured in his own web of deceit and sent to prison. In both episodes Miller was an acerbic character, but deadly dramatic.