The 1990s brought Armstrong to her best-known role, playing Patty Chase on the critically acclaimed series My So-Called Life. She later starred in several television films. In 2000, she appeared on the NBC sitcom Frasier, in the episode "Mary Christmas." In 2008, Armstrong played Penelope Kendall on ABC's Boston Legal. Armstrong remains active in films, television, and the stage. She had a recurring role in the Showtime series House of Lies as Julianne Hotschragar. She also appeared in Castle, Mad Men and NCIS.