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Ben Stiller Derek Zoolander Owen Wilson Hansel Christine Taylor Matilda Jeffries Will Ferrell Mugatu Milla Jovovich Katinka Jerry Stiller Maury Ballstein David Duchovny J.P. Prewitt Jon Voight Larry Zoolander Judah Friedlander Scrappy Zoolander Nathan Lee Graham Todd Alexandre Manning Brint Asio Highsmith Rufus Alexander Skarsgård Meekus Donald J. Trump Donald Trump Christian Slater Christian Slater Tom Ford Tom Ford Cuba Gooding Jr. Cuba Gooding Jr. Steve Kmetko Steve Kmetko Tommy Hilfiger Tommy Hilfiger Natalie Portman Natalie Portman Fabio Fabio Lenny Kravitz Lenny Kravitz Gwen Stefani Gwen Stefani Heidi Klum Heidi Klum Mark Ronson Mark Ronson Paris Hilton Paris Hilton David Bowie David Bowie Tyson Beckford Tyson Beckford Fred Durst Fred Durst Lance Bass Lance Bass Lil' Kim Lil' Kim Garry Shandling Garry Shandling Stephen Dorff Stephen Dorff Sandra Bernhard Sandra Bernhard Claudia Schiffer Claudia Schiffer Veronica Webb Veronica Webb Lukas Haas Lukas Haas Carmen Kass Carmen Kass Frankie Rayder Frankie Rayder Matt Levin Archie Justin Theroux Evil DJ Andy Dick Olga the Masseuse Andrew Wilson Hansel's Corner Guy Vikram Chatwal Hansel's Posse Kashana Hansel's Posse Jonah Luber Hansel's Posse Michael McAlpin Hansel's Posse Ève Salvail Hansel's Posse Shavo Odadjian Hansel's Posse Eliot Johnson Hansel's Posse Richard Gladys Hansel's Posse Amy Stiller Hansel's Posse John Vargas Italian Designer Jennifer Coolidge American Designer Tony Kanal French Designer Endre Hules German Designer Nora Dunn British Designer Ric Pipino Derek's Interview Hairstylist Jerry Stahl VH1 Reporter Jennifer McComb Mugatu Model Johann Urb Mugatu Bodyguard Luc Commeret Mugatu Bodyguard Herb Lieberz Time Magazine Reader Zoya Night Club Door Person Colin McNish Night Club Security Darren Copeland Night Club Security Richard Stanley Night Club Bouncer / Biff Shabazz Richardson Night Club Bouncer / Maurice Rohan Quine Night Club Bouncer Eric Winzenried Rico Svetlana Billy Zane's Date Charles Brame Abraham Lincoln James Marsden John Wilkes Booth Rudy Segura JFK Assassin Randall Slavin JFK Assassin Patton Oswalt Monkey Photographer Irina Pantaeva Irina Stan Chu Sherpa Kum Ming Ho Climber Theo Kogan Cool Tattoo Girl Lam Bor Dalai Lama Guy Luther Creek Funky Loft Guest Dechen Thurman Funky Loft Guest Kenny Max Funky Loft Guest Kina Ennui David Pressman Maori Tribesman Godfrey Janitor Derek Taj Crown Janitor Hansel Richie Rich Derelicte Doorman King Derelicte Bouncer Frederic Fekkai Derek's Derelicte Hairstylist Kevyn Aucoin Derek's Derelicte Make-up Artist Boris Kachscovsky Zoolander Center Student Mitch Winston Infomercial Director Mason Webb Derek Jr. Alexa Nikolas Story Hour Girl Victoria Beckham Victoria Beckham (uncredited) Gavin Rossdale Gavin Rossdale (uncredited) Winona Ryder Winona Ryder (uncredited) Vince Vaughn Luke Zoolander (uncredited) Billy Zane Billy Zane (uncredited) Amanda Lepore Amanda Lepore (uncredited) Klara Landrat Model (uncredited) Paulo Pascoal Model (uncredited) Anne Meara Protestor (uncredited) Tina Casciani Model (uncredited) Christiane Amanpour Christiane Amanpour (uncredited) Melania Trump Melania Knauss (uncredited) Woodrow W. Asai Prime Minister of Malaysia Scott Strasbaugh Scott Strasbaugh (as Little Kingz) Emma Bunton Emma Bunton (uncredited) Karl Lagerfeld Karl Lagerfeld (uncredited) Donatella Versace Donatella Versace (uncredited)