Owen Wilson As Hansel

Owen Wilson first partnered with Ben Stiller in The Cable Guy and the two have been working together ever since. Wilson played Zoolander’s arch nemesis-turned-unlikely ally, Hansel. After their success in Zoolander, the two starred side-by-side in comedies like Starsky & Hutch, Night At The Museum, Meet the Fockers, and in more dramatic pictures like The Royal Tenenbaums.

In 2016, Wilson reprised his role as Hansel in Zoolander 2. Today, he spends most of his time as a happy father of three.

Christine Taylor As Matilda Jeffries

Before Christine Taylor became known for her comedic roles, she starred as Marcia Brady in The Brady Bunch Movie as every teenage boy’s crush. After playing Matilda Jeffries, the uptight journalist who is the brains behind saving Derek Zoolander’s career, she continued acting with Ben Stiller. That’s because Taylor and Stiller were married from 1999 to 2017!

During that time, Taylor starred in many of her husband’s films like Dodgeball: A True Underdog Story and Tropic Thunder. Since their divorce in 2017, Taylor has stayed under the radar.

Keep reading to see which A-lister played the evil DJ.

Will Ferrell As Mugatu

Will Ferrell was already a huge star before he took on the role of fashion designer-villain Mugatu. Appearing in Zoolander only increased Ferrell’s fame and fortune. He has over 100 acting credits to his name and has stepped into the shoes of even funnier characters.

After Zoolander, he wrote and acted in other hilarious roles like Elf, Step Brothers, The Other Guys, Anchorman…the list goes on and on. Ferrell is still going strong and has three upcoming movies in 2019.

Milla Jovovich As Katinka

Mugatu’s sidekick Katinka was equal parts terrifying and beautiful, so of course, the only actress that could play the pleather-clad assassin was Milla Jovovich. At the time, Jovovich was most famous for playing Alice in Resident Evil.

The actress has continued to reprise the role of Alice in the Resident Evil franchise that is now worth more than $1.2 billion. In her downtime, Jovovich also married her Resident Evil co-star Paul W.S. Anderson and the pair have two kids together.

Justin Theroux As The Evil DJ

One of Zoolander’s best-kept secrets is that the evil DJ who has a breakdancing competition against Owen Wilson is none other than Justin Theroux. How did he end up in the role? No one knows but he seems to love the character. Theroux went on to co-write the script for Zoolander 2 and reprised the role, even appearing in costume on the red carpet and breakdancing in the trailer.

His secret acting days aren’t behind him though. Theroux most recently made a cameo appearance as The Master Codebreaker in Star Wars: The Last Jedi.

Coming up, see which Oscar-winning actor played Derek’s father.

David Duchovny As J.P. Prewitt

One of the biggest stars at the time to appear in Zoolander was David Duchovny. Riding high off the success of The X-Files, Duchovny played J.P. Prewitt, the hand model who warned Derek of the fashion industry’s evil brainwashing tactics.

Since Zoolander, Duchovny has been busy in Hollywood. He’s reprised his X-Files role of Agent Mulder for multiple movies and a reboot, and most notably starred as writer Hank Moody in the drama series Californication.

Jon Voight As Larry Zoolander

Jon Voight was one of the biggest names in Hollywood when he played the bit part of Derek’s father in Zoolander. Voight has been acting since the 1960s and won the Oscar for Best Actor in 1978. It’s safe to say his cameo wasn’t for the money or fame.

After Zoolander, Voight maintained a presence with a younger audience by appearing in both the Transformers and National Treasure franchises. He even picked up a few more Oscar nominations on his way.

Vince Vaughn As Luke Zoolander

Another huge actor that appeared as one of Derek’s family members was Vince Vaughn. He’s yet another actor who has a long history acting with Ben Stiller. Vaughn played bigger roles in other Stiller films like Starsky & Hutch and Dodgeball.

While Vaughn first gained exposure in dramatic roles in the ’90s, he’s clearly found a calling as a funnyman. His deadpan humor has worked perfectly in romcoms like The Break-Up, Wedding Crashers, and The Dilemma.

Judah Friedlander As Scrappy Zoolander

The final member of the Zoolander clan was played by one of the funniest and most vulgar actors. Judah Friedlander played Scrappy Zoolander and had minimal lines, his facial expressions gave us more than enough laughs.

While he ended up landing some other funny film roles, Friedlander’s big break was when he landed the role of Frank Rossitano in the sitcom 30 Rock. For all seven seasons of the show, Friedlander and the cast were nominated for Best Comedy Ensemble.

Jerry Stiller As Maury Ballstein

Yes, in case you didn’t know Jerry Stiller is indeed Ben Stiller’s father. But Ben didn’t just give his dad a role in the film out of pity. Jerry Stiller is a comedic genius who started out in Hollywood as a comedy duo with his wife, Anne Meara. The duo even had their own sitcom in the 1980s.

Aside from Zoolander, Jerry Stiller is best known for the role of Frank Costanza in Seinfeld and as Arthur Spooner in The King of Queens.

The next True Blood actor got his first part ever in Zoolander.

Alexander Skarsgård As Meekus

Long before he was a vampire in True Blood or swinging from trees in The Legend of Tarzan, Alexander Skarsgård was Derek Zoolander’s model roommate Meekus who started a gasoline fight in the parking lot of a gas station.

Meekus was actually Skarsgård’s first acting role in America. Despite his famous father, it took him another three years to land a leading role in HBO’s Generation Kill. In 2007, he was finally cast as vampire Eric Northman in the role that would make him famous.

Nathan Lee Graham As Todd

Nathan Lee Graham’s first and most memorable role in his career came as Todd, Mugatu’s terrified assistant. Landing the part started off a career from Graham playing hilarious sidekicks. He went on to act in Sweet Home Alabama, Hitch, and The Comeback.

While his acting credits have gone down since the 2010s, he’s increased in presence in the theatre world and appeared in three Broadway musicals. Today, he spends most of his time advocating for LGBTQ+ rights.

Andy Dick As Olga The Masseuse

We bet you had no idea that behind the double chin, Princess Leia hairdo, unibrow, and moles was comedian Andy Dick. The actor and comedian got the part thanks to his friendship with Ben Stiller. He even made his TV debut on the sketch comedy program The Ben Stiller Show.

After Zoolander, Andy Dick’s career has been plagued with scandal. Everything from drug abuse, drunk driving, and sexual battery have kept Dick from landing other roles.

Mark Ronson As The Funeral DJ

Mark Ronson is one of those people who seems to have always been pulling strings in the background. He got his start as a popular DJ in New York City which explains why he ended up cast in the role of the funeral DJ in Zoolander.

Since then though, he’s gone behind the scenes to become a world-renowned producer. Ronson has worked with everyone from Kanye West to Amy Winehouse and Bruno Mars. He most recently took home an Oscar for Best Original Song after co-writing “Shallow” for A Star Is Born.

Patton Oswalt As The Photographer

He only had a few lines in Zoolander but comedian and actor Patton Oswalt still managed to make us crack up. Oswalt played the photographer behind the photoshoot where Derek pretends to act like a monkey. Who knew the line “You’re a monkey, Derek!” would be so memorable.

Since the 2001 comedy, Oswalt has continued acting. Most notably, he played Spencer Olchin in the sitcom The King of Queens and voiced Remy in the Pixar animated flick, Ratatouille.

Keep reading to see which big celebrities played themselves in Zoolander.

David Bowie As Himself

One of the biggest and best cameos in Zoolander and (dare we say it) any film, was David Bowie as the judge of the walk-off. While Bowie was no stranger to acting, it was rare that audiences got to see him playing a comedic role. The seriousness he took to judging the walk-off made it even better.

Bowie continued acting and making music after Zoolander until January 10, 2016, when he died from complications of liver cancer.

Donald Trump As Himself

Yes, you’re looking at the cameo that Donald Trump and then-newly married wife Melania Trump made in Zoolander. Trump tells an E! News reporter, “Without Derek Zoolander, male modeling wouldn’t be what it is today.”

Of course, we all know what Donald Trump has been up to since Zoolander. Between 2001 and 2019, he hosted a hit reality television show and became the President of the United States. The one thing that hasn’t appeared to change though is his combover.

Lenny Kravitz As Himself

When Lenny Kravitz appeared as himself in Zoolander, he was at the height of his career. He won the Grammy Award for Best Male Rock Vocal Performance four years in a row between 1999 and 2002, which made it all the more hilarious that in Zoolander, he was the one presenting the top award!

Kravitz kept making music for most of the 2000s. He returned to acting in 2012 in the role of Cinna, Katniss’ stylist in The Hunger Games franchise.

Paris Hilton As Herself

The hotel heiress only appeared in Zoolander for enough time to say “Hey Derek, you rule” but it was long enough to become an iconic cameo. Just remember that at the time, Paris Hilton was a notorious socialite. In 2001, she was working as a model signed by none other than Donald Trump and making millions off nightclub promotional appearances.

Two years after her cameo, she starred in the reality series The Simple Life. After the show ended, Hilton tried her hand at singing and acting but has since stuck with fashion.

Lance Bass As Himself

There were a lot of stars who made cameos at the final Derelicte fashion show. Among them were Lance Bass, Lil’ Kim, and Fred Durst. Bass had risen to fame as part of the boy band N*SYNC but at the time was trying his hand at an acting career.

The cameo didn’t do much for him though and Bass hasn’t appeared in much since. His most note-worthy post-Zoolander venture was when he moved to Russia to try and become an astronaut.

Natalie Portman As Herself

Natalie Portman was only 20 years old and an up-and-coming movie star when she made her Zoolander cameo. She appeared talking to an E! News correspondent. When asked if she would ever date Derek Zoolander, she said the main drawback was that “He’s almost too good looking.”

Since her cameo, Portman has become one of the biggest actresses in Hollywood. Her starring roles in Black Swan, Thor, and Jackie have made her a certified A-lister.

Tyson Beckford As Himself

Tyson Beckford rose to fame in the 1990s as a male model. He was considered one of the “most beautiful people in the world” for years and became the face of Ralph Lauren Polo. That’s why it’s hilarious that Beckford didn’t appear as a clean-cut model. Instead, he got down and dirty supporting Derek in the walk-off. He even held Derek’s spit bucket.

After Zoolander, Beckford continued modeling and even hosted the Bravo program Make Me A Supermodel. In 2014, Vogue named him the greatest male model of all time. Move aside, Derek Zoolander.

Billy Zane As Himself

In 2001, Billy Zane was known for playing dramatic roles. He had starred in Titanic and Twin Peaks, which made his serious cameo all that much better. Zane tries to talk Derek out of the walk-off to no avail. Then he announced to everyone that yep, “it’s a walk-off!”

Zane has continued acting steadily since 2001 but he hasn’t landed many big roles. Today, he looks more like Mugatu than the tough, dramatic Billy Zane we once knew.

Fabio As Himself

When it comes to being really, ridiculously good looking, Fabio would be many people’s top picks in the early 2000s. Fabio made a cameo appearance as himself at the award show that Derek crashes. Fabio ended up winning the award for the best model-actor.

He went on to make a career out of cameos. Of his 32 film and television credits, only seven of them aren’t Fabio playing himself. Hey, when you build a brand around your image, why not milk it?