Ben Stiller Derek Zoolander Owen Wilson Hansel Will Ferrell Jacobim Mugatu Penélope Cruz Valentina Valencia Kristen Wiig Alexanya Atoz Fred Armisen VIP Kyle Mooney Don Atari Milla Jovovich Katinka Christine Taylor Matilda Jeffries Justin Theroux Evil DJ Nathan Lee Graham Todd Cyrus Arnold Derek Jr. Billy Zane Billy Zane Jon Daly Agent Filippo Sting Sting Benedict Cumberbatch All Beck Bennett Geoff Mille (uncredited) Jerry Stiller Maury Ballstein Olivia Munn 'Old and Lame' Show Attendee Kanye West Justin Bieber Justin Bieber Mădălina Diana Ghenea Hot Shepherdess Kim Kardashian West Kim Kardashian Ariana Grande Latex BDSM Lenny Kravitz Lenny Kravitz (uncredited) Demi Lovato Demi Lovato (uncredited) Kiefer Sutherland Kiefer Sutherland John Malkovich Chazz Spencer Anna Wintour Anna Wintour Naomi Campbell Naomi Campbell Neil deGrasse Tyson Neil deGrasse Tyson Kate Moss Kate Moss Lewis Hamilton 'Old and Lame' Show Attendee Tommy Hilfiger Tommy Hilfiger M.C. Hammer M.C. Hammer Susan Sarandon Susan Sarandon (uncredited) Alexander Skarsgård Adam Johnny Weir Warden Willie Nelson Willie Nelson Christina Hendricks Seductress Andy Dick Don Atari's Posse A$AP Rocky A$AP Rocky Jourdan Dunn Natalka Mika Mika Marc Jacobs Marc Jacobs Karlie Kloss Eve Katie Couric Katie Couric Matt Lauer Matt Lauer Amy Stiller Mom Tourist Niccolò Senni Paparazzo Nazanin Boniadi 'Old and Lame' Show Attendee Ólafur Darri Ólafsson Hasidic Man Aly Mang Fashionista (uncredited) Doris McCarthy Fashion Editor (uncredited) Soledad O'Brien Soledad O'Brien Natalie Morales Natalie Morales