From the Frat Pack to Blue Steel: The Life of Ben Stiller

Ben Stiller has starred in movies like Zoolander, Tropic Thunder, Dodgeball, and Meet the Parents, but he remains an enigma. The incredibly talented actor has lived most of his life in the public eye, but why isn’t he more famous? Why isn’t he a bigger deal in Hollywood?

Ben Stiller / Ben Stiller / Ben Stiller, Owen Wilson / Ben Stiller, Christine Taylor.
Source: Getty Images

The native New Yorker had plenty of creative energy as a kid, but his classmates bullied him. Luckily, Stiller got the last laugh after bringing us Reality Bites starring Winona Ryder and Ethan Hawke and giving one of the best character performances in Zoolander with Owen Wilson. He’s the whole package, but most of his life is a mystery.

Born Into Fame

Ben Stiller was born and raised in New York City on the Upper West Side to actor and comedian Jerry Stiller and Anne Meara. His parents frequently took him on set with them, including to The Mike Douglas Show, when he was only six years old. Stiller didn’t have a typical childhood.

A portrait of a young Ben Stiller.
Photo by Ron Galella/Ron Galella Collection/Getty Images

Stiller spent a lot of his childhood traveling, staying up late, and being surrounded by show business. Due to his parents’ careers, Stiller displayed an early interest in acting and filmmaking. He made his acting debut at age nine as a guest on his mom’s TV show, Kate McShane.

A Creative Kid

In the late 1970s, Stiller performed with NYC’s First All Children’s Theater, playing several roles, including Jack in Jack and the Magic Beanstalk. After being inspired by the series Second City Television, Stiller realized he wanted to try his hand at sketch comedy. He started writing short scripts and filmed movies with his sister.

A dated portrait of Ben Stiller.
Source: Pinterest

Stiller found many ways to fuel his creativity even if his peers didn’t understand him. His classmates picked on him, but that didn’t stop him from doing things like joining a post-punk band in high school. Stiller graduated in 1983 and continued with his love of performing.

Welcome to the Cabaret

Shortly after graduating, Stiller started performing on the cabaret circuit as an opening act for Jadin Wong. He then decided to enroll as a film student at UCLA but dropped out after nine months to move back to New York City. He wanted to be closer to his family.

A portrait of Jadin Wong.
Source: Pinterest

Stiller made his way through many acting classes, auditions, and the search for an agent. He luckily had his parents’ connections to help him get his foot in the door to land his first role in the Broadway revival of John Guare’s The House of Blue Leaves in 1986.

The Screen Was His Calling

While on Broadway, Stiller made a ten-minute short film with John Mahoney called The Hustler of Money, a spoof of Martin Scorsese’s The Color of Money. The short got the attention of the Saturday Night Live producers, and they aired it in 1987. Two years later, they offered Stiller a writing position.

A portrait of Ben Stiller.
Photo by Aaron Rapoport/Corbis/Getty Images

In the meantime, Stiller had a small role in Steven Spielberg’s Empire of the Sun. He got to work with some of the biggest names, and his on-screen role helped him become a featured performer on SNL once they realized he could do much more than write and direct.

It Didn’t Last Long

Stiller’s time on SNL didn’t last very long. They didn’t want him making any more short films, which didn’t sit right with him, so he quit after four episodes. Instead, he focused on putting together Elvis Stories, a short film about a fictitious tabloid focused on Elvis.

A still of Myers and Stiller in an episode of SNL.
Source: YouTube

The short film starred his friend John Cusack, Jeremy Piven, Mike Myers, and Andy Dick. The film was considered a success, which led him to produce another short film for MTV called Going Back to Brooklyn. It parodied LL Cool J’s hit “Going Back to Cali.”

The Ben Stiller Show

MTV’s producers were so impressed with Stiller that they offered him a 13-episode experimental series titled The Ben Stiller Show. The series mixed comedy sketches with music videos and parodied movies, music stars, and TV shows. It starred Stiller, Jeff Khan, Harry O’Reilly, and his family made appearances.

Ben Stiller poses for the press.
Photo by Ron Galella/Ron Galella Collection/Getty Images

Although the show was canceled after one season, Fox picked up the series in 1992. The series aired for an additional 12 episodes, with a 13th unaired episode broadcast by Comedy Central a few years later. Despite being the title character, Stiller kept his name at the bottom of the ratings.

Directorial Debut

Stiller had minor roles in films like Stella and Highway to Hell in the early ‘90s. His big moment came in 1992 when he was approached to direct Reality Bites, based on a script by Helen Childress. He then devoted a year and a half to work on the project.

Ben Stiller, Winona Ryder, and Ethan Hawke are in a promotional poster for the film.
Source: Copyright: Universal Pictures

He rewrote the script with Childress, raised money, and recruited cast members for the film. It was eventually released in early 1994, directed by Stiller. Winona Ryder and Ethan Hawke starred alongside Stiller, while Danny DeVito helped produce the film.

He Worked With His Parents

In its opening weekend, Reality Bites debuted as the highest-grossing film and received mixed reviews. A year later, he worked with his parents in the film Heavyweights. Stiller played the deranged fat camp leader who terrified children. The movie became an instant classic.

A still of Ben Stiller in a scene from the film.
Source: Copyright: Universal Pictures

Stiller then tackled his next directorial job with The Cable Guy, starring Jim Carrey. The film received mixed reviews, but it was noted for paying the highest salary for an actor up to that point. It also connected Stiller to Jack Black and Owen Wilson.

The Frat Pack

Like the ‘80s group known as the Brat Pack, the Frat Pack was a core group of actors who worked together on several films. Stiller was described as the “leader” of the Frat Pack, which included Jack Black, Will Ferrell, Vince Vaughn, Owen Wilson, Luke Wilson, and Steve Carell.

A dated portrait of Ben Stiller.
Photo by Ron Galella, Ltd./Ron Galella Collection/Getty Images

He was known as their leader because Stiller had multiple cameos and consistently used the other members for films that he directed and produced. Stiller has been in 20 of the 35 films that are considered Frat Pack films, although he rejected the Frat Pack label in 2008.

A Busy Schedule

In the late ‘90s, Stiller put his directing ambitions aside to focus on acting jobs. He starred in a slew of films and continued to make parody videos. In one year, he starred in three films, including Mystery Men. Stiller was quite busy at the end of the decade.

A still of Ben Stiller and Claire Forlani in a scene from Mystery Men.
Source: Copyright: Universal Pictures

Then in 2000, he starred in an additional three films. One of the films was Meet the Parents, in which he had one of his most recognizable roles as male nurse Gaylord Focker. The movie grossed over $330 million worldwide and spawned two sequels.

Unbearable Wardrobe

Meet the Parents was Stiller’s first blockbuster hit, but it wasn’t exactly pleasant to film. The producers decided to dress Stiller in clothes he hated. They wanted him to feel as uncomfortable as possible to keep him off-balance while filming.

A still of Robert De Niro and Ben Stiller in a scene from the film.
Source: Copyright: Universal Studios

They wanted him to be as uneasy as Greg would have been so he could really connect to the character. Additionally, Robert De Niro avoided Stiller on set because he wanted to maintain the tension between their characters for the cameras. It wasn’t the easiest filming experience.

The Idea of Zoolander

In 1996, MTV invited Stiller to host the Fashion Awards. He and SNL writer Drake Sather developed a short film for the awards about a male model known as Derek Zoolander. It was so well received that he developed another short film for the 1997 Fashion Awards.

A promotional still of Ben Stiller in Zoolander.
Source: Copyright: Paramount Pictures

Fast forward to 2001, and Stiller’s funny idea was turned into a full-length film. Stiller directed Zoolander and starred as Derek Zoolander. It featured cameos from celebrities like Paris Hilton, Lenny Kravitz, Heidi Klum, and David Bowie. The film was a hit, but it had problems.

Blue Steel Didn’t Work for Everyone

Zoolander’s plot was centered around an assassination attempt on a Malaysian prime minister. The film offended Malaysians, and it was banned in the country, but this didn’t hurt Stiller’s success in the film. Besides the issue with Malaysia, the film had to be re-edited.

A still of Owen Wilson and Ben Stiller in Zoolander.
Source: Copyright: Paramount Pictures

Shortly before the film’s release, shots of the World Trade Center had to be digitally removed after the September 11 terrorist attacks. Despite these small problems, Stiller was proud of the film, and people still talk about his “blue steel” modeling face.

His Signature Look

Blue Steel is Zoolander’s signature look, and it also happens to be Stiller’s signature face. The inspiration for the gag originated from real life. Whenever Stiller looked in the mirror to fix his hair or groom himself, he made that face with puckered lips.

Ben Stiller and Owen Wilson pose for the camera doing the signature look.
Source: YouTube

Stiller didn’t know he was doing that until his wife pointed out his ridiculous face. He realized he had comedy gold and decided to use it as part of his character’s persona. Thus, the Blue Steel look was born.

Love on Set

In 1999, Stiller met Christine Taylor while filming a never-broadcasted pilot for a Fox show. They had chemistry and started dating shortly after filming the show. After a year together, Stiller and Taylor got married at an oceanfront ceremony in Kauai, Hawaii.

Ben Stiller and Christine Taylor are in a scene from Zoolander.
Source: Copyright: Paramount Pictures

The two worked together on several movies, including Zooland, Dodgeball, and Tropic Thunder. Stiller and Taylor always looked completely in love on every red carpet. They had two children, Ella Olivia and Quinlin Dempsey. They had the perfect little family and moved to the suburbs.

His Kids Have Only Seen One Movie

While it must be strange to have two movie stars as parents, Stiller and Taylor don’t really show their children their movies. Most of Stiller’s films are inappropriate for children, but he admitted that Ella and Quinlin have only seen one of his movies.

Ben Stillers’ daughter talks to the media.
Photo by Gary Gershoff/Getty Images

Stiller said they have only seen Night at the Museum. He shared, “You don’t want to be the parent who’s begging your kids to watch your movies. They’ll come to when they come to it.” At least they chose one of the kid friendly ones.

He Loves Tom Cruise

It might seem strange to see one celebrity idolize another, but that is the case for Stiller. He is a huge fan of Tom Cruise and is not afraid to admit it. Stiller has impersonated Cruise for years. He even portrayed Cruise’s fictional stunt double, Tom Crooze.

Ben Stiller and Tom Cruise pose for the press.
Photo by Axelle/Bauer-Griffin/FilmMagic/Getty Images

He put on an act in a short clip called Mission: Improbable for the 2000 MTV Movie Awards. The segment was even included on the Mission: Impossible II DVD. Luckily, the feeling is mutual; Stiller and Cruise have been friends since 1996.

He Wants to Be a Millionaire

While Stiller has made millions from his movies, he still took the opportunity to appear on Who Wants to Be a Millionaire in 2001. Instead of getting money for himself, Stiller was playing for Project ALS and pledged to donate his winnings.

Ben Stiller speaks on stage.
Photo by Kevin Winter/Getty Images

He called his mom for help with one of the questions but lost on the question worth $250,000. Stiller walked away with $32,000 for his charity and was happy with the outcome. Although he would have liked to win more money for ALS, he has raised millions of dollars outside the show.

He Plays Similar Characters

Stiller has made a career out of playing characters who often find themselves in embarrassing and awkward situations. Stiller said, “Being mean is just not my thing; it feels too cheap.” When he let a magazine share his rash quotes about a red-carpet picture, he felt ashamed.

Ben Stiller attends an event.
Photo by Jerod Harris/FilmMagic/Getty Images

He didn’t know why anyone cared about his opinions on what some pop star was wearing. Stiller is a nice guy, and it feels better for him to play roles that he can relate to. He also feels more comfortable playing characters that represent his values.

He Battled Cancer

In 2014, Stiller secretly battled an aggressive form of prostate cancer. He had surgery to remove the tumor and was declared cancer-free a few months later. Stiller spoke about his experience with Howard Stern and brought his surgeon to raise awareness about prostate cancer.

A photo of Ben Stiller and Christine Taylor during an event.
Photo by Bruce Glikas/WireImage/Getty Images

When he was diagnosed, Stiller said he was shocked to hear it was cancer. He went to several doctors to get the best treatment. Stiller started getting regularly tested after he went into remission. He also encourages men to check their PSA levels.

A Sad Loss

Despite his busy career, Stiller has always been close to his parents and looked up to them. His mom, Anne Meara, left a lasting legacy in the acting world, but she sadly passed away in May 2015. He admired her talent and longevity in the industry.

A photo of Anne Meara.
Photo by Jim Spellman/WireImage/Getty Images

Stiller also looked at his parents as an example because of their relationship. They were married for 61 years until his mom passed away. Even as an adult, Stiller was pictured with his mom on the red carpet. He loved her so much.

A Shocking Split

After 17 years together, Stiller and his wife announced their split. They separated with the intention to divorce, hoping to keep things friendly for the sake of their children. They had been through many things together, including his battle with cancer, but things fell apart.

Stiller and Taylor attend an event.
Photo by James Devaney/GC Images/Getty Images

Despite their unexpected split, the estranged couple was spotted together on several occasions. They attended red carpets together as if they hadn’t split. Stiller and Taylor acted like a couple at the Emmys and an ALS Gala in 2019. It was natural and organic.

They Reconciled

Amid the pandemic, Stiller moved back in with his family to be close to them. Living under the same roof helped him reconnect with Taylor, causing them to reconcile their relationship. Stiller shared that their split was an eye-opener. He missed her terribly when they were apart.

A photo of Stiller and Taylor watching a tennis game.
Photo by Clive Brunskill/Getty Images

Stiller realized what he had lost during their breakup, and the pandemic gave him time to reflect. He didn’t want his kids growing up in a broken home, but they managed to rekindle their romance. Stiller made a conscious effort to stop sweating the small stuff.

They Didn’t Date Other People

Before they rekindled their marriage, Taylor and Stiller spent three years apart. However, during their time separated, they didn’t date other people. They continued to spend time together, just the two of them, because they always had fun and enjoyed hanging out.

The Stiller family poses for a picture.
Photo by Bruce Glikas/WireImage/Getty Images

They hadn’t agreed not to see other people, but Stiller and Taylor had no desire to date anyone else. They had been together for 17 years, and three years wouldn’t have been enough time to start over with someone new. Luckily, they got back together.

He Lost His Father

A few years after losing his mom, Stiller’s dad passed away in May 2020. Jerry Stiller was a legendary comedian and entertainer who loved his family. His father was sick for a while. Stiller said he spent time with his dad before he died, knowing the time was coming.

A dated picture of Jerry Stiller, Anne Meara, Ben Stiller, and Christine Taylor. 
Photo by Brian Ach/WireImage for Fox Broadcasting Network/Getty Images

He wanted to remember his father for his incredible sense of humor and the way he joked until the end. Stiller didn’t look at his parents like they were famous; he saw them as his mom and dad. He said he finally started to enjoy their humor when he was a teen.

Surprised by His Father’s Support

Although he was always close with his father, Stiller was surprised by his father’s admiration. He said, “Nothing was as important in my development as my family’s support.” However, he was stunned when his dad said something so nice about him.

A picture of Ben Stiller with his father.
Photo by Jason Kirk/Getty Images

His dad said, “Ben was ahead of me in a lot of ways. Everything I could never do, Ben could do.” Stiller responded, “I was funny like my dad but never really felt a competition because I would lose, hands down.” He always looked up to his dad.

He Always Wanted to Be a Director

Since Stiller was a child, he wanted to be a director. His parents gave him a Super 8 camera for his tenth birthday, and he started making short films with his sister. Over time, his dreams became a reality, and Stiller directed several successful films.

A photo of Ben Stiller on a radio show.
Photo by Noam Galai/Getty Images

Most people don’t look at the director’s credit on many films, or they would know that Stiller has acted, wrote, produced, and directed at least 20 films. Stiller has helped direct both Zoolander films, Tropic Thunder and The Secret Life of Walter Mitty.

He Created a Production Company

Besides his work as a director, Stiller has also produced many films and started a production company. As a Star Trek fan, Stiller named his production company Red Hour Films after an alien riot featured in one of the episodes. The company was established in 2001.

Ben Stiller attends an event.
Photo by Leon Bennett/WireImage/Getty Images

In 2015, Red Hour partnered with Bold Films, a financing and production company that focuses on independent films and “providing an artistic haven for creative talent.” Stiller has turned his attention to working behind the scenes rather than in front of the camera.

He Doesn’t Act Anymore

Throughout his life, Stiller always wanted to be a director, but acting took the front seat. Stiller’s last film was in 2013 because he stopped acting to focus on directing and producing. Stiller said the creative experience is more fulfilling as a director.

A photo of Ben Stiller at a Senate Foreign Relations Committee Hearing.
Photo by Paul Morigi/Getty Images

Stiller likes that directing is easier, but it has a different kind of pressure. He has a total of 20 directing credits, including the new series Severance, which had received excellent ratings. He is also set to direct Super Sad True Love Story, an upcoming series, and Bag Man.

He Compares Himself to Others

It might be hard to believe that celebrities compare themselves to others, but Stiller admitted he often does that. He said, “In the film business, particularly, it’s almost impossible to shut out these kinds of thoughts: ‘Why didn’t I get the part?’”

A movie still of Ben Stiller in Zoolander 2.
Source: Copyright: Paramount Pictures

Stiller shared that he questioned why some of his movies weren’t more successful because it’s human nature to think those things. He emphasized that it is important to learn how to cope with those doubts. He tries not to let it get him down.

Giving Back

Stiller should be better known for his philanthropy work because he has done so much of it. Since 2016, he has been involved with UNHCR, the UN Refugee Agency, after meeting refugees in Germany and Jordan. He also became a Goodwill Ambassador in 2018.

Ben Stiller testifies at a Senate Foreign Relations Committee Hearing.
Photo by Paul Morigi/Getty Images

Stiller visited Guatemala, where he met with refugees from El Salvador, Guatemala, and Honduras. This is just one of many charities he supports. He has also raised millions for ALS and the Elizabeth Glaser Pediatric AIDS Foundation. Stiller wants to teach his children important values.

He’s an Award Winner

The Ben Stiller Show might not have been a huge success, but Stiller won an Emmy after the show’s cancellation. He also won a DGA Award for Outstanding Directorial Achievement for his work on Escape at Dannemora in 2019. Stiller is an accomplished actor/director/producer.

Ben Stiller eats a Golden Globe made of banana bread onstage.
Photo by Kevin Mazur/Getty Images

While he has been nominated for for many awards, Stiller also holds the record at the Razzie Awards for the most nominations in one year. He was nominated in 2004 for Worst Actor in five of the six films in which he appeared, including Along Came Polly and Dodgeball.

He’s Working on a Documentary

Stiller admired his parents so much that he is working on a documentary about them. He wants to showcase their brilliance, humor, generosity, and struggles. The project brings up memories of all the times they were there for him and when it felt like they weren’t.

Ben Stiller speaks on stage.
Photo by Bennett Raglin/Getty Images

He said the documentary wouldn’t be finished for another year. Stiller visited the apartment where he grew up, and it brought back many memories. It reminded him that he always had a place to go when he needed it.

He Has a High Attention to Detail

When it comes to directing, Stiller is detail-oriented and likes to make everything perfect, down to the smallest sounds in the background of a shot. While working on the series Severance, he went through almost every second of the show to make sure every detail was flawless.

A headshot of Ben Stiller.
Photo by Gregg DeGuire/FilmMagic/Getty Images

Esquire followed him into the editing room, and they saw how particular he was with the sound effects. In one instance, Stiller looked at his notepad, called out a time, and said the breaking noise of a car was too loud.

How Much Is Ben Stiller Worth?

As of 2022, Stiller has a net worth of $200 million. Through his hard work and commitment to his craft, he has gained a lot of respect in the industry. He raked in millions of dollars for projects like Blades of Glory, Meet the Fockers, and Madagascar.

Ben Stiller attends an event.
Photo by Leon Bennett/WireImage/Getty Images

Working as a director has been a successful career move for Stiller. His projects such as The Cable Guy and Tropic Thunder grossed over $100 million. He has also bought and sold plenty of real estate over the years, contributing to his high net worth.

He Worked With His Son

While Stiller doesn’t want to make his children go into the entertainment business, he has worked with his son. When Quinlin was three, he lent his voice for a small part in Madagascar: Escape 2 Africa. It was exciting for Stiller to bring his son to work.

A photo of Quinlin and Ben Stiller watching a basketball game.
Photo by James Devaney/Getty Images

Quinlin played a young version of his father’s character, Alex, as a cub. He shared the role with another young boy, Declan Smith. Stiller was proud of his son for being able to recite all of his lines at such a young age.

Impersonation King

Besides Tom Cruise, Stiller has impersonated many celebrities, including Bono, Bruce Springsteen, and David Blaine. In an interview with Parade, Stiller said Robert Klein, George Carlin, and Jimmie Walker were his inspirations for his comedy career. However, Stiller doesn’t think he is that funny.

A photo of Ben Stiller wearing a costume as he speaks onstage.
Photo by Kevin Winter/Getty Images

Stiller said he admires funny people, but “that’s not me.” He is a humble man and claims he can’t tell a joke even if you paid him. It’s interesting to hear that from someone who has mainly been in comedy films. Maybe he is just modest.

Not a Fan of Sitcoms

His father might have been well-known for his sitcom career playing Frank Costanza in Seinfeld, but Stiller is not a fan of the genre. Stiller clarified, “It’s not that the people who work on them aren’t talented or creative, but there’s something about that world that’s predictable.”

A still from the television series Seinfeld.
Source: Copyright: NBC

It’s safe to say you will never see Stiller acting in a sitcom any time soon. He might love comedy, but he never wants to do something obvious and repetitive. Since he put his acting days behind him, Stiller has tried to be as innovative as possible.

He’ll Do Anything for His Craft

When Stiller was acting, he would go to great lengths to make a character convincing, even if he had to suffer. In Night at the Museum, there were plenty of special effects to bring wooly mammoths, dinosaurs, and a talking Easter Island head to life.

A still of Ben Stiller in the film Meet The Fockers.
Source: Copyright: DreamWorks Pictures

However, Stiller insisted on forgoing the special effects and worked several scenes with a real monkey. He filmed a slap-fight scene with the monkey, and when it was Stiller’s turn to hit him back, the monkey was done for the day.

No One Wanted to Make This Movie

Although Dodgeball is now a classic Stiller movie, it initially didn’t have much appeal to those in Hollywood. Several studios turned it down when the screenplay was sent around. However, Stiller’s production company, Red Hour, decided to buy it because he believed it could be a hit.

A promotional still of Ben Stiller in Dodgeball.
Source: Copyright: 20th Century Fox

Red Hour struggled to secure funding to make the film and worried they would have to discard it. Luckily, Fox eventually backed them, but only after they made the cast and crew take several pay cuts. Ironically, it really was an underdog story.

What Could Have Been

One of the few instances of Stiller turning down a role was when he passed on the opportunity to voice the main character in a hit DreamWorks film. Stiller planned to voice Megamind in the animated movie of the same name but backed out because of his busy schedule.

Ben Stiller attends an event.
Photo by Presley Ann/FilmMagic/Getty Images

Instead, he remained a co-producer and voiced one of the minor characters in the movie. Stiller ended up playing Bernard, which was a much smaller commitment that fit into his schedule. He was working on Little Fockers and Tower Heist around the same time.

An Old Idea

Although Tropic Thunder came out in 2008, Stiller came up with the film’s premise while working on Empire of the Sun in 1987. He directed, co-wrote, and starred in Tropic Thunder with Robert Downey Jr. and Jack Black two decades after coming up with the idea.

A still of Robert Downey Jr. in a scene from the film.
Source: Copyright: Paramount Pictures

Stiller had a small part in the WWII drama Empire of the Sun, but it gave him a big idea. He continued to develop the script as he rose to fame. The film was a success because of its all-star cast, including a cameo from Tom Cruise.

He Was in the WWE

Maybe it’s a stretch to say Stiller was in WWE’s Raw in the early 2000s. Stiller, Samuel L. Jackson, and Arnold Schwarzenegger all made guest appearances on Smackdown. While he was nowhere near the size of the other wrestlers, Stiller held his own.

A video still of Ben Stiller in the ring.
Source: YouTube

The 5’7” actor probably looked small next to the other wrestler, but he was happy to be part of the show. Stiller is carefully posed to be taller than his larger co-stars in his movies, so maybe the WWE worked some Hollywood magic too.

He Made Headlines

Stiller is one of those stars that people should be talking about more but don’t. He has gotten more press in recent months due to the success of Severance on Apple TV. However, his skills are highly underrated. Stiller has plenty of projects in the works, including a sequel to Dodgeball.

A still from the show Severance.
Source: YouTube

He also recently made headlines after being called out at a tennis match. Tennis pro Nick Kyrgios pointed at Stiller in the crowd to say that the heckler shouldn’t tell him how to play tennis because he doesn’t tell Stiller how to act.