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The first few minutes of "Kissing Jessica Stein" are pretty routine.It features the feisty grandma and a "all-men-are-losers" montage straight out of a Meg Ryan movie.In one of the more subtle examples Jessica walks up her spiral staircase- her steps exactly in time with a recurring piano note in the song.Finally, I'm a guy and I never got the whole lesbian-chic thing.In 1989, Steen broke onto the big screen with the movie musical Sing.While in Toronto, Steen garnered roles on Canadian series and American made-for-TV movies until 1991, when she elected to move to New York City.The movie starts out seemingly filled with stereotypes (male, gay, Jewish, ect.) but before the end everyone gets their say and the true characters come out. It is probably the funniest movie -written by and made for women- that I have ever seen. One of those movies where you nudge your neighbor to see if they got the joke too. If there's one thing in this low budget indie flick that is cinematically brilliant it's the audio visual montages.
That's where we pick up with Jessica Stein (cute beyond words Jennifer Westfeldt) being constantly hounded by her hyperbolically obsessed mother to hurry up and "find someone" like her brother.The movie doesn't show women's lesbian tendencies in the casual way of, say, Chasing Amy, but explores the sheer oddity of it as a novelty plot gimmick.One of the best scenes in the film is Helen's gay friend voicing offense to the unfair way she seems to choose her sexuality whenever it's convenient for her.In 1997, she was cast as District Attorney Elizabeth Gardner in the movie Trial & Error, working with Jeff Daniels and Michael Richards, to whom she gave his first screen kiss. Her performance earned a rave review from Roger Ebert on his syndicated show, Siskel & Ebert.