Anna Faris

Shelley

Colin Hanks

Oliver

Emma Stone

Natalie

Kat Dennings

Mona

Hugh Hefner

Hugh Hefner

Christopher McDonald

Dean Simmons

Beverly D'Angelo

Mrs. Hagstrom

Katharine McPhee

Harmony

Rumer Willis

Joanne

Kiely Williams

Lilly

Dana Goodman

Carrie Mae

Monet Mazur

Cassandra

Tyson Ritter

Colby

Sarah Wright

Ashley

Rachel Specter

Courtney

Owen Benjamin

Marvin

Holly Madison

Holly Madison

Bridget Marquardt

Bridget Marquardt

Kendra Wilkinson

Kendra Wilkinson

Tyler Spindel

Steve

Sara Jean Underwood

Herself - Playmate

Lauren Michelle Hill

Herself - Playmate

Hiromi Oshima

Herself - Playmate

Dan Patrick

Cop

Sean Salisbury

Sean Salisbury

Matt Leinart

Matt Leinart

Shaquille O'Neal

Shaquille O'Neal

Nick Swardson

Playboy Photographer

Jay Hayden

Kip

Danni Katz

Girl at Panhellenic

Matt Barr

Tyler

Chris Titone

Guy at Bar

Michael Bernardi

Karaoke Trio

Mike Falkow

Karaoke Trio

Josh Richman

Paramedic

Tony Ervolina

Paramedic

Nikki DeLoach

Tall Blonde Girl

Linsey Godfrey

Short Brunette Girl

Katheryn Cain

Girl at Panhellenic

Ashley Schneider

Girl at Panhellenic

Jennifer Tisdale

Phi Iota Mu

Adam Shapiro

Mona's Interviewee

Julia Lea Wolov

Sweet Prostitute

Jonathan Loughran

Tall Prostitute

Kathleen Gati

Boutique Manager

Robert Harvey

Guy at Pool Table

Ryan Rottman

Calendar Buyer

Charles Robinson

Francis

Emily Wilson

Brittany

Allen Covert

Waiter #2 (uncredited)

Ameona Almund

Hot Girl