Early work When he was approximately 15, Stiller obtained a small part with one line on the television soap opera
Guiding Light, although in an interview he characterized his performance as poor. He was later cast in a role in the 1986 Broadway revival of
John Guare's
The House of Blue Leaves, alongside
John Mahoney; the production would garner four
Tony Awards. In 1989 Stiller wrote for and appeared on
Saturday Night Live as a featured performer. However, since the show did not want him to make more short films, he left after four episodes. The film starred friends and co-stars
John Cusack,
Jeremy Piven,
Mike Myers,
Andy Dick, and Jeff Kahn.
The Ben Stiller Show Producers at MTV were so impressed with
Back to Brooklyn that they offered Stiller a 13-episode show in the experimental "vid-com" format. Titled
The Ben Stiller Show, this 1990 series mixed comedy sketches with music videos and parodied various television shows, music stars, and films. It starred Stiller, along with main writer Jeff Khan and Harry O'Reilly, with his parents and sister making occasional appearances. Among the principal writers on
The Ben Stiller Show were Stiller and
Judd Apatow, with the show featuring the ensemble cast of Stiller,
Janeane Garofalo,
Andy Dick, and
Bob Odenkirk. Both
Denise Richards and
Jeanne Tripplehorn appeared as extras in various episodes. Throughout its short run,
The Ben Stiller Show frequently appeared at the bottom of the ratings, even as it garnered critical acclaim and eventually won an
Emmy Award for "
Outstanding Writing in a Variety or Music Program" posthumously.
Directorial debut '' at
Camp Pendleton in August 2008 In the early 1990s, Stiller had minor roles in films such as
Stella and
Highway to Hell as well as a cameo in
The Nutt House. In 1992, Stiller was approached to direct
Reality Bites, based on a script by Helen Childress. Stiller devoted the next year and a half to rewriting the script with Childress, fundraising, and recruiting cast members for the film. It was eventually released in early 1994, directed by Stiller and featuring him as a co-star.
Reality Bites debuted as the fifth highest-grossing film over the President Day opening weekend and received mixed reviews. Stiller joined his parents in the family film
Heavyweights (1995), in which he played two roles. Following
Heavyweights, he had a brief uncredited role in
Adam Sandler's
Happy Gilmore (1996) where he played Hal L., the sadistic orderly running the nursing home. Next, he had lead roles in
If Lucy Fell and
Flirting with Disaster, before tackling his next directorial effort with
The Cable Guy, which starred
Jim Carrey. Stiller once again was featured in his own film, as twins. The film received mixed reviews, but was noted for paying the highest salary for an actor up to that point, as Carrey received $20 million for his work in the film. The film also connected Stiller with future
Frat Pack members
Jack Black and
Owen Wilson. discussing
Severance at
SXSW 2025 Also in 1996, MTV invited Stiller to host the
VH1 Fashion Awards. Along with
SNL writer Drake Sather, Stiller 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 about the character for the 1997 VH1 Fashion Awards and eventually remade the skit into a film. In 1999, he starred in three films, including
Mystery Men, where he played a superhero wannabe called Mr. Furious. He appeared in a segment on the July 26 episode of
WWF's
RAW is WAR to promote the then-upcoming movie and found himself on the wrong end of Intercontinental Champion
Jeff Jarrett's Figure-4 Leg Lock. He returned to directing with a new spoof television series for Fox titled
Heat Vision and Jack, starring Jack Black. However, the show was not picked up by Fox after its pilot episode and the series was cancelled. In 2000, Stiller starred in three more films, including one of his most recognizable roles, a male nurse named Gaylord "Greg" Focker in
Meet the Parents, opposite
Robert De Niro. The film was well received by critics, grossed over $330 million worldwide, and spawned two sequels. Also in 2000, MTV again invited Stiller to make another short film, and he developed
Mission: Improbable, a spoof of
Tom Cruise's role in
Mission: Impossible II and other films. In 2001, Stiller directed his third feature film,
Zoolander, in which he also starred as Derek Zoolander. The film featured multiple cameos from a variety of celebrities, including
Donald Trump,
Paris Hilton,
Lenny Kravitz,
Heidi Klum, and
David Bowie, among others. The film was banned in
Malaysia (as the plot centered on an assassination attempt of a Malaysian prime minister), while shots of the
World Trade Center were digitally removed and hidden for the film's release after the
September 11 terrorist attacks. After Stiller worked with
Owen Wilson in
Zoolander, they joined forces again for
The Royal Tenenbaums. Over the next two years, Stiller continued with a starring role in the film
Duplex, and cameos in
Orange County and
Nobody Knows Anything! He has guest-starred on several television shows, including an appearance in an episode of the television series
The King of Queens, in a flashback as the father of the character Arthur (played by Jerry Stiller). He also made a guest appearance on
World Wrestling Entertainment's
WWE Raw. In 2004, Stiller appeared in six different films, all of which were comedies, and include some of his highest-grossing films:
Starsky & Hutch,
Envy (which he co-starred with
Jack Black in),
Dodgeball: A True Underdog Story,
Anchorman: The Legend of Ron Burgundy (in which he had an uncredited cameo),
Along Came Polly, and
Meet the Fockers. While the critical flop
Envy only grossed $14.5 million, the most successful film of these was
Meet the Fockers, which grossed over $516.6 million worldwide. He also made extended guest appearances on
Curb Your Enthusiasm and
Arrested Development in the same year. He appeared on shows such as
Friends and
Extras, the latter of which earned him a
Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series nomination. In 2005, Stiller appeared in
Madagascar, which was his first experience as a voice actor in an animated film.
Madagascar was a massive worldwide hit, and spawned the sequels
Madagascar: Escape 2 Africa in 2008 and ''
Madagascar 3: Europe's Most Wanted in 2012. In 2006, Stiller had cameo roles in School for Scoundrels and Tenacious D in The Pick of Destiny; he was executive producer of the latter. In December 2006, he had the lead role in Night at the Museum. Although not a critical favorite, it earned over $115 million in ten days. In 2007, Stiller starred alongside Malin Åkerman in the romantic comedy The Heartbreak Kid''. The film earned over $100 million worldwide despite receiving mostly negative reviews. , 2017 In 2008, Stiller directed, co-wrote, co-produced, and starred in the film
Tropic Thunder, with
Robert Downey Jr. and
Jack Black; Stiller had originally conceived of the film's premise while filming
Empire of the Sun in 1987. In 2009, he starred with
Amy Adams in
Night at the Museum 2: Battle of the Smithsonian, a sequel to
Night at the Museum. In 2010, Stiller made a brief cameo in
Joaquin Phoenix's mockumentary ''
I'm Still Here and played the lead role in the comedy-drama Greenberg. He again portrayed Greg Focker in the critically panned but financially successful Little Fockers, the second sequel to Meet the Parents
. He originally had planned to voice the titular protagonist of Megamind along with Robert Downey Jr., but later dropped out and was replaced by Will Ferrell while still remaining an executive producer and voicing a minor character in the film, a museum curator named Bernard. Stiller starred with Eddie Murphy and Alan Alda in Tower Heist (2011), about a group of maintenance workers planning a heist in a residential skyscraper. He produced, directed, and starred in The Secret Life of Walter Mitty'', which was released in 2013. After starring in and directing
Zoolander 2 (2016), a critical failure, Stiller's next directorial project was the
Showtime miniseries
Escape at Dannemora, for which he received two Emmy Award nominations. In 2018 and 2019, Stiller played
Michael Cohen on
Saturday Night Live for six episodes. In 2021, Stiller signed on to co-write and direct
Bag Man, a
Focus Features adaptation of
the 2018 podcast about the kickback scandal that led to the resignation of Vice President
Spiro Agnew. As of October 2023, the movie remained in pre-production. The filming was scheduled to start in Washington, DC and Budapest in November 2025>. Stiller executive produces and directs many episodes of the
Apple TV+ series
Severance, which premiered in 2022. In 2024, Stiller made his acting comeback after seven years with the holiday films
Nutcrackers and
Dear Santa, the latter also featuring Jack Black and having Stiller in an uncredited role. While promoting the films Stiller appeared on the popular interview show
Hot Ones. In 2024, it was announced that Stiller and De Niro were in talks to star in a fourth
Meet the Parents film. In December 2024, Stiller was featured in a music video trailer for singer
SZA's new album
Lana, singing her song "Drive". Stiller reprised his role as Hal L. in
Happy Gilmore 2, a sequel to
Happy Gilmore that premiered on July 25, 2025. He was confirmed to appear in
The Dink (2025), a comedy film about the sport of pickleball directed by Josh Greenbaum and co-produced with Stiller.
Writing Stiller co-wrote a comedic
New York Times bestseller with
Janeane Garofalo in 1999, titled
Feel This Book: An Essential Guide to Self-Empowerment, Spiritual Supremacy, and Sexual Satisfaction, a spoof of the self-help books prevalent at the time. =="Frat Pack"==