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In 1995, Flockhart became acquainted with actors such as Dianne Wiest and Faye Dunaway when she appeared in the movie Drunks.
Later that year, Flockhart starred in Jane Doe as a drug addict.
In 1997, Flockhart was asked to audition for the starring role in David E. 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 traveled to Los Angeles to audition for the part, which she won.
Throughout that year, she continued to work on Broadway, playing the role of Natasha in Anton Chekhov's Three Sisters.While there, she attended a specialized and competitive class, lasting from a.m. In her sophomore year at Rutgers, Flockhart met aspiring actress Jane Krakowski, the best friend of her roommate.Later, they both would work together on Ally Mc Beal.Actress Julie Harris felt Flockhart should be hired without further auditions, claiming that she seemed ideal for the part.Flockhart received a Clarence Derwent Award for her performance.
She starred as the title character in the legal comedy-drama series Ally Mc Beal (1997–2002), Kitty Walker in the drama series Brothers & Sisters (2006–2011) and Cat Grant in the superhero drama series Supergirl (2015–2019).