Although born in New York City, Chloe Webb grew up in various cities on the East Coast-wherever her father’s job as a road and bridge designer took the family. She often stayed with her grandmother (who resided in New York City) and attended Bishop Grimes High School (then a Catholic all-girls high school), and sang with the high school band. When she was 16 years old she enrolled at the Boston Conservatory of Drama and Music, and later Berkeley College of Music. Initially, she pursued singing (her passion), singing in bars she was too young to drink in. Although she greatly enjoyed singing, she soon realized she was better at acting.
Webb made her film debut in Sid and Nancy (1986), in which she portrayed Nancy Spungen, the heroin-addicted girlfriend of rock singer Sid Vicious (portrayed by Gary Oldman). Her performance garnered awards as Best Actress from the National Society of Film Critics, the Boston Film Critics and the San Francisco Film Critics. Through the ’80s, other film roles emerged, including Louisa Kracklite, the wife to American architect Stourley Kracklite (portrayed by Brian Dennehy) in The Belly of an Architect (1987), Danny DeVito’s kooky girlfriend in Twins (1988), and in Ghostbusters II (1989) she plays Elaine, a psychic who shares her “end of the world” predictions when Dr. Peter Benkman (Bill Murray) interviews her on his show on his show “The World of the Psychic”.
The following decade, Webb starred alongside Bob Hoskins and Denzel Washington in the comedy Heart Condition (1990) (in which Webb plays tender-souled call-girl Crystal), she then went on to star in the made-for-TV film Lucky Day (1991); the film tells the story of Allison Campbell (Webb), a cognitively impaired woman who wins the $2million lottery, but her fortune is tainted when the prize sparks a feud between her alcoholic mother (Olympia Dukakis), and Allison’s sister-caregiver (Amy Madigan). Through the decade, Webb continued to work prolifically, providing her craft to film and television projects, including the short-lived television miniseries Tales of the City (1993), the independent drama film A Dangerous Woman (1993), and the blockbuster comedy-drama Practical Magic (1998).
More recently, Webb can be seen in Showtime’s American comedy-drama television series Shameless (2011) (in which she plays Monica Darrgen Gallagher, the estranged wife of Frank (William H. Macy) and mother of Fiona (Emmy Rossum), Lip (Jeremy Allen White), Ian (Cameron Monaghan), Debbie (Emma Kenney), Carl (Ethan Cutkosky) and Liam (Brenden Sims).