Hickenlooper caught attention for his work early on: earning a 1987 nomination for a Student Academy Award for "Newark Needs Insurance". After making "Hearts of Darkness", he turned his attention to another controversial filmmaker with "Picture This: The Times of Peter Bogdanovich in Archer City, TX" (Showtime, 1991) and also filmed a profile of actor-director Dennis Hopper. Segueing to fictional works, he directed "Ghost Brigade/Grey Knight" (1993), a film in which supernatural forces are affecting Civil War troops forcing Union and Confederate officers to unite in an investigation, that received respectable notices. "The Low Life" (1995) was a semi-autobiographical work about a repressed Yale-educated writer trying to cope with living in L.A. while "Persons Unknown" (HBO, 1996) was a crime thriller about a security guard who falls prey to two thieving sisters. Invoking comparisons to Peter Bogdanovich's "The Last Picture Show" (1971), Hickenlooper wrote and directed the elegiac "Dogtown" (1997), about a failed Hollywood actor who returns to his home town and discovers the residents think he is a success. After a brief stint producing segment for the reality-based ABC series "Vital Signs" (1997), he raised eyebrows by turning his attentions to "Big Brass Ring" (1999), about a politician with a secret, adapted from an unproduced script by Orson Welles.