In the late '90s, Westfeldt was just another working no-name actress, alternately playing dizzy or neurotic blondes on TV series like Two Guys and a Girl (back when Pizza Place was part of the sitcom's title) and Judging Amy. In order to take control of her career trajectory, she began honing her own material, including Lipschtick, a series of sketches she wrote and performed with fellow starlet Heather Juergensen. Together they wrote, produced and starred in the delightful indie comedy Kissing Jessica Stein, playing a pair of romantically challenged urban heterosexuals who decide to give lesbianism a try. The flick was an art-house hit, racking up numerous film-festival awards and showcasing Westfeldt's quirkily endearing personality. In 2004, the multitalented actress made her Broadway debut in a revival of Wonderful Town, which highlighted her solid singing and dancing chops and earned her a Tony nomination. After starring in another indie comedy that she wrote and produced, Ira & Abby, in 2006, she continued to make small-screen appearances on such series as Notes from the Underbelly, Grey's Anatomy and 24.