Jake Gyllenhaal as Jamie Randall

Anne Hathaway as Maggie Murdock

Oliver Platt as Bruce Winston

Hank Azaria as Dr. Stan Knight

Josh Gad as Josh Randall

Gabriel Macht as Trey Hannigan

Judy Greer as Cindy

Jill Clayburgh as Nancy Randall

George Segal as Dr. James Randall

Kate Jennings Grant as Gina

Katheryn Winnick as "Lisa"

Kimberly Scott as Gail

Peter Friedman as California Man

Nikki DeLoach as Christy

Natalie Gold as Dr. Helen Randall

Megan Ferguson as Farrah

Michael Benjamin Washington as Richard

Bingo O'Malley as Sam

Dorothy Silver as Sophie

Lucy Roucis as UN Convention Parkinson's Speaker

Joan Augustin as Joan

Michael Chernus as Jerry

Kate Easton as Amber

Michael Buffer as Pfizer Convention MC

Maïté Schwartz as Texas

Maximilian Osinski as Ned

Ian Harding as Pfizer Trainee #1

Josh Breslow as Pfizer Trainee #2

Ian Novick as Pfizer Trainee #3

Tess Soltau as Pfizer Trainee #4

Constance Brenneman as Pfizer Trainee #5

Nicole Thomas as Pfizer Trainee #6

Jasper Soffer as Pfizer Trainee #7

Kwame Rakes as Doctor in Parking Lot

Scott Cohen as Ted Goldstein

Sharon Wilkins as La Boheme Receptionist

Brian Hutchison as Homeless Man

Dana Dancho as Smiling Receptionist

Lisa Ann Goldsmith as Nurse Janice

Rick Applegate as Viagra Doctor

Ray Godshall Sr. as Friendly Senior

Jean Zarzour as Viagra Sample Nurse

Harry O'Toole as Man with Walker

Jennifer Delaeo as Viagra Receptionist

Deidre Goodwin as Viagra Nurse #1

Geneva Carr as Viagra Nurse #2

Vanessa Aspillaga as Viagra Nurse #3

Patricia Cray as Kindly-looking Woman

Kristin Spatafore as Convention Girl #1

Larissa Emanuele as Convention Girl #2

Loretta Higgins as PET Scan Doctor

Kimberly M. Rizzo as Front Desk Receptionist

Jason Bernard as Quack Doctor

Nicole Perrone as Determined Receptionist

Jo Newman as Bree

Christina Fandino as Khae

Teri Clark as ER Receptionist

Kevin McClatchy as Justin

Jaimie Alexander as Carol (uncredited)

Diedra Arthur-O'Ree as Medical Convention Attendee (uncredited)

Stephanie Bankosh as Pharmaceutical Rep (uncredited)

David Barckhoff as Medical Convention Vendor (uncredited)

Robert R. Bell as Doctor (uncredited)

Aaron Bernard as Bartender (uncredited)

Ralph Browning as Medical Convention Attendee (uncredited)

Alissa Collins as Tea Woman (uncredited)

Kyle Fields as Party Rep (uncredited)

Joe Forgione as Pfizer Trainee #8 (uncredited)

Nicole George as Viagra Receptionist (uncredited)

Ryan Goimarac as Pfizer Drug Rep. Graduate (uncredited)

Mark Golik as Physician (uncredited)

John W. Iwanonkiw as Viagra Guy (uncredited)

Sharyn Kmieciak as UN Convention Attendee (uncredited)

Wayne Leya as UN Convention Attendee (uncredited)

David Dale McCue as Pfizer Rep. (uncredited)

David Morse as Tony Lerma, Lilly Sales Rep. (uncredited)

Christian Pearson as Physician (uncredited)

Chris A. Riskus as Trade Show Patron (uncredited)

Nayli Russo as PJ Party Girl (uncredited)

Michael K. Sieg as Pfizer Rep. (uncredited)

Morgan Wolk as Lilly Spokesmodel (uncredited)

Conan O'Brien as Self (archive footage) (uncredited)

Gwyneth E. Larsen as Dancer (as Gwyneth Larsen)

Brooke Miyasaki as Dancer

Jackson Nunn as Viagra Guy #2 (uncredited)