In spring 1989, Flockhart made her first television appearance in a minor role in an episode of Guiding Light as a babysitter. She made her professional debut on the New York stage, appearing in Beside Herself alongside Melissa Joan Hart at the Circle Repertory Theatre. Two years later, Flockhart appeared in the television movie Darrow. Though she later appeared in films Naked in New York (1993) Read more...

In 1997 Flockhart was requested to audition for the starring role in David E. Kelley's FOX television series, Ally McBeal. Kelley, having heard of Flockhart, wanted her to audition for the contract part. Though Flockhart at first hesitated due to the necessary commitment to the show in a negotiable contract, she was swayed by the script and travelled to Los Angeles to audition for the part, which Read more...

Flockhart played the role of Helena in the 1999 film version of Shakespeare's A Midsummer Night's Dream. In 2000, she appeared in Things You Can Tell Just by Looking at Her and Bash: Latter-Day Plays, later accompanying Eve Ensler to Kenya in order to protest violence against women, particularly female genital mutilation. Flockhart also starred in the off-Broadway production of Ensler's The Vagina Read more...