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Kissing Jessica Stein (2001)

97 min | Comedy, Drama, Romance

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A woman searching for the perfect man instead discovers the perfect woman.

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Cast	+ Add Cast
38 cast members

Name	STARmeter	Known for
Jennifer Westfeldt Jessica Stein Jessica Stein See fewer	Members only	Friends with Kids (2011)
Tovah Feldshuh Judy Stein Judy Stein See fewer	Members only	Lady in the Water (2006)
Esther Wurmfeld Grandma Esther Grandma Esther See fewer	Members only	Kissing Jessica Stein (2001)
Hillel Friedman Rabbi Rabbi See fewer	Members only	Kissing Jessica Stein (2001)
Ben Feldman Self Self See fewer	Members only	Black Dynamite (2009)
Robert Ari Sidney Stein Sidney Stein See fewer	Members only	Music of the Heart (1999)
David Aaron Baker Dan Stein Dan Stein See fewer	Members only	Edge of Darkness (2010)
Jennifer Carta Rachel - Dan's Fiancée Rachel - Dan's Fiancée See fewer	Members only	It's About Time (I) (2005)
Ben Weber Larry Larry See fewer	Members only	Twister (I) (1996)
Brian Stepanek Peter Peter See fewer	Members only	Nicky, Ricky, Dicky & Dawn (2014)
Nick Corley Howard Howard See fewer	Members only	Law & Order (1990)
Jackie Hoffman Joan Joan See fewer	Members only	Garden State (2004)
John Cariani Chuck Chuck See fewer	Members only	Showtime (2002)
Scott Cohen Josh Meyers Josh Meyers See fewer	Members only	The 10th Kingdom (2000)
Christopher Berger Malaprops Guy Malaprops Guy See fewer	Members only	Little Noises (1991)
Hayden Adams Weird Smooth Guy Weird Smooth Guy See fewer	Members only	Hamlet (2009)
Kevin Sussman Calculator Guy Calculator Guy See fewer	Top 5000	Burn After Reading (2008)
Jim J. Bullock Not-Yet-Out Gay Guy Not-Yet-Out Gay Guy See fewer	Members only	Spaceballs (1987)
Heather Juergensen Helen Cooper Helen Cooper See fewer	Members only	The Hammer (2007)
Alysia Reiner Schuller Gallery Artist Schuller Gallery Artist See fewer	Members only	Orange Is the New Black (2013)
Carson Elrod Sebastian Sebastian See fewer	Members only	Wedding Crashers (2005)
Michael Mastro Martin Martin See fewer	Members only	Paterno (2018)
Tibor Feldman Roland Roland See fewer	Members only	Enchanted (2007)
Michael Showalter Stephen Stephen See fewer	Members only	Wet Hot American Summer (2001)
Michael Ealy Greg Greg See fewer	Top 5000	Barbershop (2002)
Naomi Scott Seductive Woman at Gallery (as Naomi Sablan) Seductive Woman at Gallery (as Naomi Sablan) See fewer	Members only	The Overnight (2015)
Jon Hamm Charles Charles See fewer	Top 5000	Mad Men (2007)
Allen Fitzpatrick Matthew Matthew See fewer	Members only	My Little Girl (1986)
Julie Lauren Josh's Date Josh's Date See fewer	Members only	Rabbit Hole (2010)
Jimmy Palumbo Cheesy Pick-up Guy #1 Cheesy Pick-up Guy #1 See fewer	Members only	The Family (I) (2013)
Thomas L. Bolster Cheesy Pick-up Guy #2 (as Thomas Bolster) Cheesy Pick-up Guy #2 (as Thomas Bolster) See fewer	Members only	Crimes and Misdemeanors (1989)
Vinny Vella Cab Driver (as Vinnie Vella) Cab Driver (as Vinnie Vella) See fewer	Members only	Casino (1995)
Peter Hirsch Stanley Stanley See fewer	Members only	Ira & Abby (2006)
Idina Menzel Bridesmaid Bridesmaid See fewer	Top 5000	Frozen (I) (2013)
Adele Reichman Grandma Interrogating Helen Grandma Interrogating Helen See fewer	Members only	Kissing Jessica Stein (2001)
Amy Wilson Bookstore Saleswoman Bookstore Saleswoman See fewer	Members only	Kinsey (2004)
Ilana Levine Helen's New Girlfriend Helen's New Girlfriend See fewer	Members only	Friends with Kids (2011)
Dalit Berkowitz Barfly (uncredited) Barfly (uncredited) See fewer	Members only	Colony (2016)