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Kissing Jessica Stein (2001) Poster

Trivia

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The cab scene where Helen and Jessica talk about blending lipstick was filmed after the filmmakers hailed a cab, paid the driver $20, the director drove, the director of photography was in the front seat and the sound woman climbed in the back trunk.
Some background shots were removed from the film prior to its release because they showed the World Trade Center.
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The role of the mother was written especially for Tovah Feldshuh.
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Many "extras" in the film were people who just happened to be walking by the cameras during filming in New York City.
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The film is based on a play called "Lipschtick", the original title of the film was "Seeking Same."
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Future Broadway and Disney megastar Idina Menzel (RENT, Wicked, Frozen) has a small role in this movie.
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Kevin Sussman, who went on to play Stu, the Comic Store Owner in Big Bang Theory, has a small role in this film.
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Most of the film was shot in New York City and Connecticut but a couple of scenes, including the bookstore scene between Josh and Jessica, were re-shot in Los Angeles.
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Small screen '80s celebrity Jim J. Bullock, from Too Close For Comfort and Hollywood Squares, has a small role in this film.
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Film debut of Michael Ealy.
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Spoilers 

The trivia item below may give away important plot points.

In the beginning of the film, Jessica is set up on a blind date by a co-worker and friend. The date was played by Jon Hamm, with whom Jennifer Westfeldt was in a real life relationship with at the time.
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See also

Goofs | Crazy Credits | Quotes | Alternate Versions | Connections | Soundtracks

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