She came to prominence with supporting parts in the films Mystic Pizza (1988) and Say Anything... (1989), before establishing herself as one of the key figures of 1990s independent cinema through starring roles in Bright Angel (1990), Dogfight (1991), Household Saints, Short Cuts (both 1993), The Addiction (1995), I Shot Andy Warhol, Girls Town (both 1996), Pecker (1998), and A Slipping-Down Life (1999).

Alongside her work on smaller-scale projects, Taylor has encountered mainstream success with parts in films such as Born on the Fourth of July (1989), Rudy (1993), Ransom (1996), The Haunting (1999), High Fidelity (2000), Brooklyn's Finest, Public Enemies (both 2009), The Conjuring (2013), and Maze Runner: The Scorch Trials (2015).

Other credits include The Notorious Bettie Page (2005), Starting Out in the Evening (2007), The Promotion (2008), Being Flynn (2012), To the Bone, Leatherface (both 2017), Eli (2019), and Paper Spiders (2020).

In 1991, Taylor played Grace, the witty and romantic step-daughter of Faye Dunaway, in Arizona Dream (released 1993), directed by Emir Kusturica, co-starring Johnny Depp, Vincent Gallo and Jerry Lewis.

In 1998 she appeared in the X-Files episode "Mind's Eye", and was nominated for a Primetime Emmy Award for Outstanding Guest Actress in a Drama Series.

The same year, she appeared in John Waters' film Pecker, alongside Edward Furlong, Christina Ricci and Mary Kay Place.

The film, co-starring Courtney Love, centered on a Long Island mother and housewife who leaves her husband to pursue her dream of studying science.

[5] She starred in the Lifetime cable network's hour-long comedy-drama series State of Mind, as a New Haven therapist dealing with a divorce and a parade of quirky clients.

[8][9][10] The following year she co-starred in Maze Runner: The Scorch Trials, as Dr. Mary Cooper, "a doctor who helps Thomas and his fellow Gladers".

New York Supreme Court Justice Arlene Goldberg issued a protection order forbidding him from contacting Taylor and requiring him to undergo counseling.

In 1996, she received a Special Recognition award from the Sundance Film Festival for her performance in Mary Harron's I Shot Andy Warhol, in which she portrayed Valerie Solanas.