Kissing Jessica Stein Cast
The cast of Kissing Jessica Stein.
Jennifer Westfeldt
as Jessica Stein

Played the role of Jessica Stein.

Heather Juergensen
as Helen Cooper

Portrayed the character of Helen Cooper.

Scott Cohen
as Josh Myers

Took on the role of Josh Myers.

Jackie Hoffman
as Joan

Brought the character Joan to the screen.

Tovah Feldshuh
as Judy Stein

Portrayed Judy Stein.

Michael Mastro
as Martin

Played the role of Martin.

Carson Elrod
as Sebastian

Took on the role of Sebastian.

Jon Hamm
as Charles

Portrayed the character Charles.

David Aaron Baker
as Dan Stein
Esther Wurmfeld
as Grandma Esther
Hillel Friedman
as Rabbi
Ben Feldman
as Ben Feldman
Ben Weber
as Larry
Brian Stepanek
as Peter
Jennifer Carta
as Rachel - Dan's Fiancée
Idina Menzel
as Bridesmaid
Vinny Vella
as Cab Driver
John Cariani
as Chuck
Kevin Sussman
as Calculator Guy
Jim J. Bullock
as Not-Yet-Out Gay Guy
Hayden Adams
as Weird Smooth Guy
Christopher Berger
as Malaprops Guy
Alysia Reiner
as Schuller Gallery Artist
Tibor Feldman
as Roland
Michael Showalter
as Stephen
Michael Ealy
as Greg
Allen Fitzpatrick
as Matthew
Julie Lauren
as Josh's Date
Jimmy Palumbo
as Cheesy Pick-up Guy #1
Ilana Levine
as Helen's New Girlfriend
Naomi Scott
as Seductive Woman at Gallery
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