After studying film theory at Yale, George Hickenlooper forged a name for himself in the annals of the film aesthetic by writing and co-directing (with Eleanor Coppola) "Hearts of Darkness: A Filmmaker's Apocalypse", a behind-the-scenes 1991 Showtime documentary on the making of Francis Ford Coppola's "Apocalypse Now". He was also noted as the co-producer, editor and director of the short "Some Folks Call It a Sling Blade", screened at the 1994 Sundance Film Festival. Written by and starring Billy Bob Thornton (as convicted killer Karl Childers), the short was a warm-up for Thornton who later directed the 1996 feature "Sling Blade". In Hickenlooper's version, Molly Ringwald was the young woman interviewing Karl who, in turn, recounts his story.
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.