The daughter of Mark Miller, an actor best known for his starring role on the mid-1960s TV sitcom Please Don't Eat the Daisies, actress Penelope Ann Miller was born in California and raised in Texas. After a year of attending Menlo College, Miller dropped out to train with acting coach Herbert Berghof. Her first role of note was as ditsy ingenue Daisy in the Neil Simon Broadway comedy Biloxi Blues, a role she would later recreate in the film version. For her role in Our Town she was nominated for a Tony award in 1989. In 1987, the blonde, saucer-eyed actress made her film debut in the wacked-out comedy Adventures in Babysitting, after which she costarred with popular leading men ranging from Pee-Wee Herman (Big Top Pee-Wee) to a GOlden Globe nominated performance alongside Al Pacino in Carlito's Way. Some of Miller's best known film roles have included that of Marlon Brando's enigmatic daughter in The Freshman (1990), a brief turn as silent film actress Edna Purviance in Chaplin (1992), and the svelte 1930s pulp heroine Margot Lane in The Shadow (1994).
As the 1990s progressed Miller alternated ever more frequently between television and film, tempering high profile roles in The Shadow (1994) and The Relic (1997) with more intimate small screen roles in mini-series The Last Don (1997) and as the titular character in the true-life television feature The Mary Kay Letorneau Story: All American Girl (2000). If her roles in the following years weren't as high profile as in the previous decade, solid performances in Along Came a Spider (2001) and Rudy: The Rudy Giuliani Story (2003) eventually led to a role in the popular but shortlived Norm Macdonald sitcom A Minute with Stan Hooper. Cast as the titular character's (Macdonald) city-slicker wife, the coupled opted to eschew the city for small town life to Newhart-like effect. Her gift for comedy more obvious than ever, Miller was subsequently cast in the made for television feature National Lampoon's Thanksgiving Family Reunion (2003).