Though this venue usually is reserved for juniors and seniors, Harold Scott insisted that Flockhart perform there in his production of William Inge's Picnic.

Flockhart graduated with a Bachelor of Fine Arts in theater in 1988 from Rutgers as one of the few students who successfully completed the acting course.

[6][7] In spring 1989, Flockhart made her first television appearance in a minor role in an episode of Guiding Light as a babysitter.

She also appeared in a one-hour afternoon special for Lifestories: Families in Crisis, playing a teenager battling an eating disorder.

Flockhart made her professional debut on the New York stage, appearing in Beside Herself alongside Melissa Joan Hart, at the Circle Repertory Theatre.

In 1997, Flockhart was asked to audition for the starring role in David E. Kelley's Fox television series Ally McBeal.

Though she hesitated due to the necessary commitment to the show in a negotiable contract, she was swayed by the script and traveled to Los Angeles to audition for the part, which she won.

Flockhart also appeared on the June 29, 1998, cover of Time magazine,[10] placed as the newest iteration in the evolution of feminism, relating to the ongoing debate about the role depicted by her character.

Flockhart's character was significant throughout the series' first four years, but her appearances were reduced for the 2010–2011 season, coinciding with the departure of TV husband Rob Lowe.

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 remained with the show (albeit as a recurring character), despite her previous aversion to working outside Los Angeles.

[18] Regarding playing Radziwill in an interview with The New York Times, Flockhart said, “Truman Capote recognized that she was living in her sister’s shadow... and he would say things: ‘You’re so much prettier.