Jake Gyllenhaal

Character: Jamie Randall

Anne Hathaway

Character: Maggie Murdock

Oliver Platt

Character: Bruce Winston

Hank Azaria

Character: Dr. Stan Knight

Josh Gad

Character: Josh Randall

Gabriel Macht

Character: Trey Hannigan

Judy Greer

Character: Cindy

Jill Clayburgh

Character: Nancy Randall

George Segal

Character: Dr. James Randall

Kate Jennings Grant

Character: Gina

Katheryn Winnick

Character: "Lisa"

Kimberly Scott

Character: Gail

Peter Friedman

Character: California Man

Nikki DeLoach

Character: Christy

Natalie Gold

Character: Dr. Helen Randall

Megan Ferguson

Character: Farrah

Michael Benjamin Washington

Character: Richard

Bingo O'Malley

Character: Sam

Dorothy Silver

Character: Sophie

Lucy Roucis

Character: UN Convention Parkinson's Speaker

Joan Augustin

Character: Joan

Michael Chernus

Character: Jerry

Kate Easton

Character: Amber

Michael Buffer

Character: Pfizer Convention MC

Maïté Schwartz

Character: Texas

Maximilian Osinski

Character: Ned

Ian Harding

Character: Pfizer Trainee #1

Josh Breslow

Character: Pfizer Trainee #2

Ian Novick

Character: Pfizer Trainee #3

Tess Soltau

Character: Pfizer Trainee #4

Constance Brenneman

Character: Pfizer Trainee #5

Nicole Thomas

Character: Pfizer Trainee #6

Jasper Soffer

Character: Pfizer Trainee #7

Kwame Rakes

Character: Doctor in Parking Lot

Scott Cohen

Character: Ted Goldstein

Sharon Wilkins

Character: La Boheme Receptionist

Brian Hutchison

Character: Homeless Man

Dana Dancho

Character: Smiling Receptionist

Lisa Ann Goldsmith

Character: Nurse Janice

Rick Applegate

Character: Viagra Doctor

Ray Godshall Sr.

Character: Friendly Senior

Jean Zarzour

Character: Viagra Sample Nurse

Harry O'Toole

Character: Man with Walker

Jennifer Delaeo

Character: Viagra Receptionist

Deidre Goodwin

Character: Viagra Nurse #1

Geneva Carr

Character: Viagra Nurse #2

Vanessa Aspillaga

Character: Viagra Nurse #3

Patricia Cray

Character: Kindly-looking Woman

Kristin Spatafore

Character: Convention Girl #1

Larissa Emanuele

Character: Convention Girl #2

Loretta Higgins

Character: PET Scan Doctor

Kimberly M. Rizzo

Character: Front Desk Receptionist

Jason Bernard

Character: Quack Doctor

Nicole Perrone

Character: Determined Receptionist

Jo Newman

Character: Bree

Christina Fandino

Character: Khae

Teri Clark

Character: ER Receptionist

Kevin McClatchy

Character: Justin

Jaimie Alexander

Character: Carol (uncredited)

Diedra Arthur-O'Ree

Character: Medical Convention Attendee (uncredited)

Stephanie Bankosh

Character: Pharmaceutical Rep (uncredited)

David Barckhoff

Character: Medical Convention Vendor (uncredited)

Robert R. Bell

Character: Doctor (uncredited)

Aaron Bernard

Character: Bartender (uncredited)

Ralph Browning

Character: Medical Convention Attendee (uncredited)

Alissa Collins

Character: Tea Woman (uncredited)

Kyle Fields

Character: Party Rep (uncredited)

Joe Forgione

Character: Pfizer Trainee #8 (uncredited)

Nicole George

Character: Viagra Receptionist (uncredited)

Ryan Goimarac

Character: Pfizer Drug Rep. Graduate (uncredited)

Mark Golik

Character: Physician (uncredited)

John W. Iwanonkiw

Character: Viagra Guy (uncredited)

Sharyn Kmieciak

Character: UN Convention Attendee (uncredited)

Wayne Leya

Character: UN Convention Attendee (uncredited)

David Dale McCue

Character: Pfizer Rep. (uncredited)

David Morse

Character: Tony Lerma, Lilly Sales Rep. (uncredited)

Christian Pearson

Character: Physician (uncredited)

Chris A. Riskus

Character: Trade Show Patron (uncredited)

Nayli Russo

Character: PJ Party Girl (uncredited)

Michael K. Sieg

Character: Pfizer Rep. (uncredited)

Morgan Wolk

Character: Lilly Spokesmodel (uncredited)

Conan O'Brien

Character: Self (archive footage) (uncredited)

Gwyneth E. Larsen

Character: Dancer (as Gwyneth Larsen)

Brooke Miyasaki

Character: Dancer

Jackson Nunn

Character: Viagra Guy #2 (uncredited)