Kissing Jessica Stein (2001) | Full Cast

Charles Herman-Wurmfeld

DIRECTOR

Jennifer Westfeldt

Jessica Stein

Heather Juergensen

Helen Cooper

Tovah Feldshuh

Judy Stein

Esther Wurmfeld

Grandma Esther

Hillel Friedman

Rabbi

Ben Feldman

Self

Robert Ari

Sidney Stein

David Aaron Baker

Dan Stein

Jennifer Carta

Rachel - Dan's Fiancée

Ben Weber

Larry

Brian Stepanek

Peter

Nick Corley

Howard

Jackie Hoffman

Joan

John Cariani

Chuck

Scott Cohen

Josh Meyers

Christopher Berger

Malaprops Guy

Hayden Adams

Weird Smooth Guy

Kevin Sussman

Calculator Guy

Jim J. Bullock

Not-Yet-Out Gay Guy

Alysia Reiner

Schuller Gallery Artist

Carson Elrod

Sebastian

Michael Mastro

Martin

Tibor Feldman

Roland

Michael Showalter

Stephen

Michael Ealy

Greg

Naomi Scott

Seductive Woman at Gallery

Jon Hamm

Charles

Allen Fitzpatrick

Matthew

Julie Lauren

Josh's Date

Jimmy Palumbo

Cheesy Pick-up Guy #1

Thomas L. Bolster

Cheesy Pick-up Guy #2

Vinny Vella

Cab Driver

Peter Hirsch

Stanley

Idina Menzel

Bridesmaid

Adele Reichman

Grandma Interrogating Helen

Amy Wilson

Bookstore Saleswoman

Ilana Levine

Helen's New Girlfriend

Dalit Berkowitz

Barflyuncredited

Lee Kheel

Old Woman at Antique Storeuncredited

Marshall Dancing Elk Lucas

Guyuncredited