Jennifer Westfeldt

Jennifer Westfeldt

Born in Guilford, CT, Westfeldt was the daughter of Patrick McLoskey Westfeldt, an electrical engineer of Swedish descent, and Constance (née Meyers), a social worker and family therapist. Jessica was raised according to her mother's Jewish faith and as a teenager attended Guilford High School, where she first became enthralled with live theater, performing in several productions throughout her four years at the school. Following graduation from Guilford, Westfeldt began her college education at Yale University, enrolling in the theater department and performing regularly with an a cappella group. Having earned her degree from Yale, the determined Westfeldt moved to New York City and began her pursuit of an acting career in earnest. While appearing in some two dozen off-Broadway productions, the ambitious actress also collaborated with friend and writing partner Heather Juergensen on "Lipschtick," a series of comedy sketches about the hardships of dating in the Big Apple. Also taking part in that early production was Jon Hamm, a struggling actor Westfeldt had met during a previous visit to Los Angeles and had invited to perform in the show. Although not initially attracted to Hamm - she reportedly found him "arrogant" - the two became close while working on "Lipschtick" and eventually began dating after she made the jump to Hollywood later in 1997. Defying the odds from the very beginning, Westfeldt quickly landed a supporting role on the aptly-titled sitcom "Two Guys, a Girl and a Pizza Place" (ABC 1998-2001), starring future Hollywood hunk Ryan Reynolds. Although the show would later trim its name to the less-restricting "Two Guys and a Girl," Westfeldt would not remain beyond its first season, having accepted an attractive development deal with 20th Century Fox. The result was a co-starring role on the ill-fated "Holding the Baby" (Fox 1998-99), a sitcom about a recently divorced young executive (Jon Patrick Walker) who becomes involved with his charming grad-student nanny (Westfeldt) which lasted barely a season. Pressing forward, the actress embarked on another failed TV pilot, picked up a recurring role in three episodes of the popular legal drama "Judging Amy" (CBS 1995-2005) and took part in the independent drama "See Jane Run" (2001). Just as her frustration over a lack of progress and opportunities threatened to reach the breaking point, a long-gestating project from the past returned to breathe new life into Westfeldt's nascent career.Having extended one of their "Lipschtick" skits into a full-length screenplay, Westfeldt and Juergensen spent two years raising financial backing for their feature film debut, "Kissing Jessica Stein" (2001). A charming and slightly left-of-center romantic comedy, it told the story of Jessica (Westfeldt), a young Jewish copywriter who unexpectedly finds a potential solution to her endless dating woes in the arms of the more sexually adventurous Helen (Juergensen). An instant hit at the indie festivals, it garnered strong reviews, generally favorable response from the gay community, and substantial press for Westfeldt and her collaborator. Even better, the film was a financial success. Produced for less than $1 million, it grossed more than seven times that amount at the box office. Flush with success, the multi-talented Westfeldt celebrated by returning to New York where she made her Broadway debut singing and dancing in a revival of the musical revue "Wonderful Town" in 2003. After earning a Tony nomination and winning a Theater World Award for her performance in "Town," the actress was next seen on movie screens opposite Paul Schneider in the indie romantic comedy "50 Ways to Leave Your Lover" (2004). Westfeldt took another swing at television success when she joined the cast of "Notes from the Underbelly" (ABC, 2007-08), a short-lived sitcom about a couple (Westfeldt and Peter Cambor) whose unexpected pregnancy invites the advice and interference of well-meaning family and friends. As the sitcom struggled in the ratings, Westfeldt returned to the recipe of her earlier success by writing and starring in another quirky romantic comedy, "Ira and Abby" (2007). Unfortunately, the tale of an on-again, off-again marriage between a free spirit (Westfeldt) and a neurotic Jewish Ph.D. candidate (Chris Messina) failed to attract a fraction of the attention "Jessica Stein" had enjoyed. Closing out the decade, she made several guest spots in episodes of "Private Practice" (ABC, 2007-2013) and "Grey's Anatomy" (ABC, 2005-), as well as a starring turn in the made-for-TV romance "Before I Say 'I Do'" (Hallmark Channel, 2009). Rounding things out in 2010 was a recurring role as reporter and suspected terrorist collaborator Meredith Reed on the final season of the hit action series "24" (Fox, 2001-2010), starring Kiefer Sutherland. Once again taking charge of her professional destiny, Westfeldt wrote and starred in "Friends with Kids" (2012), a film that also marked her directorial debut. Another independently produced romantic comedy, it revolved around platonic friends (Westfeldt and Adam Scott) who decide to have a baby together in the hope of avoiding the marital pitfalls suffered by their other friends - married couples whose relationships all faltered after having children. The film co-starred Chris O'Dowd, Maya Rudolph, Kristin Wiig and Jon Hamm. Westfeldt next appeared in episodes of cult comedy hit "Childrens Hospital" (Adult Swim 2008-) and "Girls" (HBO 2012-). By Bryce Coleman