Zoolander (2001 franchise)

Zoolander (September 28, 2001)
Ben Stiller - Owen Wilson - Will Ferrell - Christine Taylor - Milla Jovovich - Jerry Stiller - David Duchovny

Asio Highsmith - Alexander Manning - Alexander Skarsgård

and Jon Voight

Zoolander 2 (February 12, 2016)
Ben Stiller - Owen Wilson - Will Ferrell - Penélope Cruz - Kristen Wiig - Fred Armisen - Kyle Mooney

Milla Jovovich - Christine Taylor - Justin Theroux - Nathan Lee Graham - Cyrus Arnold - Billy Zane - Jon Daly

Sting - Benedict Cumberbatch

Zoolander (2001 film)

 * Ben Stiller - Derek Zoolander Sr.


 * Owen Wilson - Hansel McDonald, Derek's best friend


 * Will Ferrell - Jacobim Mugatu, Derek's rival


 * Christine Taylor - Matilda Jeffries-Zoolander, Derek's 1st wife


 * Milla Jovovich - Katinka Ingabogovinanana, Hansel's henchwoman


 * Jerry Stiller - Maury Ballstein


 * David Duchovny - J.P. Prewett


 * Asio Highsmith - Rufus, Derek's best friend


 * Alexander Manning - Brint, Derek's best friend


 * Alexander Skarsgård - Meekus, Derek's best friend


 * Jon Voight - Larry Zoolander, Derek's father

Zoolander 2 (2016 film)

 * Penélope Cruz - Valentina Valencia-Zoolander, Derek's 2nd wife


 * Kristen Wiig - Alexanya Atoz, Valentina's rival


 * Fred Armisen - VIP


 * Kyle Mooney - Don Atari


 * Justin Theroux - Evil DJ, Jacobim's henchman


 * Nathan Lee Graham - Todd, Jacobim's henchman


 * Cyrus Arnold - Derek Zoolander Jr., Derek's son


 * Billy Zane - as Himself


 * Jon Daly - Agent Filippo


 * Sting - as Himself, Hansel's father


 * Benedict Cumberbatch - All