THEN: Ben Stiller was already a comedy star before he turned his "Zoolander" short films into a feature film. He plays Derek Zoolander, a model who finds himself in the middle of an assassination conspiracy. Though it was Stiller's third time directing a feature, it was his first full-length screenplay, which he cowrote with Drake Sather and John Hamburg.
NOW: Stiller has since appeared in a number of comedies and has continued to direct and produce films. He's reprising his role in the sequel and also serves as a cowriter and director.
THEN: Owen Wilson made his film debut in Wes Anderson's "Bottle Rocket" (1996) and landed roles in films such as "Armageddon" and "Shanghai Noon" before playing a rival model, Hansel, in "Zoolander."
NOW: Stiller and Wilson first worked together in "The Cable Guy" and have appeared in 12 films together, including "Zoolander No. 2."
THEN: Will Ferrell was an established cast member on "Saturday Night Live" and had already starred in two "Austin Powers" films and "A Night at the Roxbury" when he portrayed the villainous Jacobim Mugatu.
NOW: Ferrell, a comedy A-lister, has continued to star in movies such as "Elf," "Anchorman," and "Step Brothers." He'll next appear in "Zeroville" and is returning as the villain fresh out of prison in "Zoolander No. 2."
THEN: Cabaret artist Nathan Lee Graham made his feature-film debut as Todd, Mugatu's assistant, in "Zoolander."
NOW: He went on to appear in a few more projects, including "Hitch," "The Comeback," and most recently "Hug-O-Gram." He will return in "Zoolander No. 2."
THEN: Known for "Mulholland Drive," Justin Theroux popped up as Evil DJ in "Zoolander."
NOW: He's reprising his role in the sequel and also serves as a cowriter on the film. He's currently starring in HBO's "The Leftovers" and is filming "The Girl on the Train," based on the best-selling novel of the same name. He also cowrote the script for Ben Stiller's "Tropic Thunder."
THEN: Known for portraying Marcia Brady in "The Brady Movie," Christine Taylor starred as Zoolander's love interest in the original film. She married Ben Stiller in 2000.
NOW: She is reprising her role in the sequel.
THEN: Comedian Andy Dick made a cameo appearance in "Zoolander" as Olga the masseuse.
NOW: While his name doesn't appear on the cast list on IMDb, he posted a photo on Instagram in June 2015 saying that he would be making a cameo in "Zoolander 2." He recently made a guest appearance on an episode of "Workaholics."
THEN: The Oscar-winning Jon Voight played Zoolander's disapproving coal-miner father.
NOW: He'll next appear in the "Harry Potter" prequel spin-off "Fantastic Beasts and Where to Find Them," based on J.K. Rowling's book of the same name.
THEN: Vince Vaughn had appeared in a number of films, including "Swingers" and "The Lost World: Jurassic Park," before playing Zoolander's brother, Luke, in the film.
NOW: He gained wider recognition in the following years, starring in comedies such as "Starsky & Hutch," "Dodgeball," and "Wedding Crashers." He recently starred in the widely-criticized second season of HBO's "True Detective."
THEN: Judah Friedlander started his career doing standup and landed his first acting role in 1999. Playing Zoolander's other brother, Scrappy, was one of his earliest roles.
NOW: He went on to appear in a number of comedies and is known for his role in "30 Rock." He's currently voicing a character on Fox's "Bordertown."
THEN: Ben Stiller's father, Jerry Stiller, is a comedic actor who made an appearance as Zoolander's agent. He finds himself mixed up in the assassination plot but chooses to come clean at the end.
NOW: Jerry continued to act in comedies such as "The King of Queens" and voiced a fish in Disney's animated series "Fish Hooks."
THEN: Though she appeared in "Dazed and Confused," Milla Jovovich's break was playing Leeloo in "The Fifth Element." She played the evil Katinka in "Zoolander."
NOW: Jovovich went on to star as Alice in all five of the films in the "Resident Evil" franchise. She's set to reprise her role in "Resident Evil: The Final Chapter."
THEN: David Duchovny was well-known for playing agent Fox Mulder on Fox's "The X-Files" when he popped up in "Zoolander" as "the world's greatest hand model."
NOW: Duchovny has since appeared in shows such as "Californication" and "Aquarius." He reprised the role of Mulder for this year's "X-Files" revival.
THEN: Alexander Skarsgard was a relatively unknown actor when he auditioned for "Zoolander" while on vacation in America, but he was cast as Meekus, one of Zoolander's roommates.
NOW: He caught his big break in the 2008 HBO miniseries "Generation Kill." That same year, he landed the role of Eric Northman on another HBO hit, "True Blood." He's starring as Tarzan in this year's "The Legend of Tarzan."
THEN: James Marsden was best known as Scott Summers (aka Cyclops) in "X-Men" before he showed up and flashed the "Blue Steel" as John Wilkes Booth.
NOW: He is set to appear this year in HBO's "Westworld," a sci-fi Western based on the film of the same name, and is voicing the lead character in the movie "Henchmen."
