Jennifer Westfeldt

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. She continued to land parts but they were mostly in failed pilots and little-seen indies, and while her Tony-nominated turn in a Broadway revival of Wonderful Turn highlighted her solid singing and dancing chops, she was still searching for her breakthrough project. In 2007 she made two moves to up her profile: writing and starring in the indie marriage comedy Ira and Abby, and taking a gig as a jittery pregnant wife in the sitcom Notes from the Underbelly.