Back in 2001, when pretty blonde actress Jennifer Westfeldt grew frustrated with her inability to land some of Hollywood’s juicier acting roles, she decided to write her own ticket – co-writing, producing – and most importantly – starring in the indie feature film hit, “Kissing Jessica Stein.” With this popular film, Westfeldt caught the attention of both straight and gay audiences alike with her charming portrayal of a neurotic singleton living in New York City who contemplates the potential benefits of a sapphic romance, after every man she meets is either taken or simply not up to her standards.
Born Feb. 2, 1971 in Guilford, CT, Westfeldt’s first love was the theater. She first began acting while attending Guilford High, starring in several school productions throughout those four years. After getting an Ivy League education at Yale University, Westfeldt moved to New York City, NY and found herself a busy theater actress, starring in more than 25 Off Broadway productions. But like many before and after her, Hollywood beckoned, and in 1997, she followed a friend to Los Angeles for pilot season, swiftly landing a regular role in the sitcom “Two Guys, a Girl and a Pizza Place” (ABC 1998-2001). Unfortunately, Hollywood proved to be less reliable and more fickle than New York. After one season on the sitcom, Westfeldt left the show to accept a development deal with Twentieth Century Fox, which in turn, led to a starring role in the ill-fated series, “Holding the Baby” (Fox 1998-99) – which fizzled after only two episodes. In 2001, she got a smaller part on a bigger series when she won a recurring role on “Judging Amy” (CBS 1995-2005). That same year, Westfeldt took another shot, making another unsuccessful run at television fame by shooting the failed WB pilot “The Gene Pool.”
With television a frustrating proposition, she turned her attention toward the big screen, starring in the independent feature “See Jane Run.” It was around that time that Westfeldt, growing increasingly irritated with the lack of strong female roles available, decided to collaborate with her friend, Heather Juergensen, another unknown actress/writer whom Westfeldt had met at a writer’s workshop back in the late 1990’s. Together they created “Lipschtick,” a play about the hardships of the New York dating scene. “Lipschtick” eventually evolved into “Kissing Jessica Stein” with Westfeldt playing the neophyte lesbian, Jessica, and Juergensen portraying Helen, her slightly more experienced love interest. What resulted was a romantic comedy with a modern twist that went on to become the film festival circuit darling, but not before Westfeldt and Juergensen saved their screenplay from languishing in development limbo. After two years, sans studio help, the two actors raised enough money to seize back control of the script and produce the indie version themselves. The film was made for less than one million and grossed nearly eight.
Writing and acting weren’t her only talents – Westfeldt could also sing. In 2004, she returned to the stage, making her Broadway debut in the musical “Wonderful Town.” Her performance netted her a Tony nomination for Best Actress in a Musical. She didn’t win the Tony, but she won a 2004 Theater World Award.
In 2006, hoping to repeat her earlier success by creating her own roles, Westfeldt wrote herself another plum part. This time around it was in “Ira and Abby” (2006) – a quirky romantic comedy bearing her signature role of sweet, neurotic New York Jew with a troubled romantic life. Westfeldt played Abby, one half of a couple who marry, divorce, remarry, divorce and remarry each other yet again. The hardworking thespian returned to television that same year, shooting the ABC pilot “Notes from the Underbelly,” about a woman dealing with an unplanned pregnancy.