Ben Stiller and Owen Wilson are one of Hollywood’s most accomplished and successful actor-comedians. Both have careers spanning three decades, with Stiller’s screen debut in 1986 and Wilson’s debut in 1994. Ben Stiller and Owen Wilson are part of the seven-man Hollywood “Frat Pack.”
The Frat Pack, a group of actors who have collaborated on multiple movie projects, also includes Will Ferrell, Vince Vaughn, Steve Carell, Jack Black, Luke Wilson, and Paul Rudd. Although they’re all yet to feature in one movie, several films have starred a few of them together. Listed from earliest to latest release dates, these are the 7 times Ben Stiller and Owen Wilson have co-starred in a movie.
1. The Cable Guy
The 1996 satirical black comedy The Cable Guy was the first film that co-starred Ben Stiller and Owen Wilson. However, Ben Stiller, who was the movie’s director, appears in an uncredited role as Sam Sweet/Stan Sweet. The character, a former child star in trial for the murder of his twin brother, appears on television as a trending news. On the other hand, Wilson played a minor role as Robin’s (Leslie Mann) date.
Wilson’s character is accosted by the Cable Guy in the restaurant’s bathroom. Although Stiller and Wilson never share screen, The Cable Guy is still the first time the actors were featured in the same movie. The 1996 The Cable Guy was led by Jim Carrey and co-starred Matthew Broderick and Jack Black. Besides gaining a cult following over the years, the movie was a theatrical success, grossing $102.8 million against a production budget of $47 million.
2. Permanent Midnight
In the David Veloz-directed independent drama Permanent Midnight, Ben Stiller played the lead role, with Owen Wilson cast as a supporting character. Stiller portrayed Jerry Stahl, while Wilson played Nicky. Owen Wilson’s character is introduced during flashbacks as a fellow drug addict and friend of Stiller’s character.
Permanent Midnight centered around the life of Jerry Stahl and how his drug addiction caused him to lose everything and leave him in debt. With the movie based on the autobiography of Jerry Stahl, audiences watched Stiller deliver a stellar against-type performance. Permanent Midnight also starred Elizabeth Hurley, Connie Nielsen, Peter Greene, and Sandra Oh.
3. Meet the Parents
In Meet the Parents, Ben Stiller was cast in the lead role as Greg Focker. The character is a Jewish American male nurse looking to win the approval of his girlfriend, Pam Byrnes (Teri Polo), overbearing father (Robert De Niro) before proposing. Greg Focker is the center of a series of awkward and comedic situations as he struggles to make a good impression on his future father-in-law. Owen Wilson, cast as Kevin Rawley, played the wealthy and seemingly perfect Pam Byrnes’ ex-fiancé.
Kevin’s success and charm created an additional source of tension for Greg. With Kevin as Pam’s father’s choice for a romantic partner, Greg constantly feels overshadowed by Kevin. Both characters added to the film’s humor, with Stiller’s Greg enduring countless embarrassing moments, while Wilson’s Kevin served as the effortlessly likable contrast.
The 2000 romantic comedy was a huge success, raking $330.4 million at the Box Office against a $55 million budget. Meet the Parents had two sequels; Meet the Fockers (2004) and Little Fockers (2010). Stiller and Wilson reprised their roles in the sequels, with each becoming Box Office successes. With the sequels, this makes additional two movies where Ben Stiller and Owen Wilson worked together.
4. Zoolander
The following year, Ben Stiller and Owen Wilson co-starred again in Stiller’s 2001 comedy Zoolander. Stiller played the lead role as Derek Zoolander, a dimwitted but famous male model. The character becomes the target of a brainwashing plot by the fashion industry to assassinate the Prime Minister of Malaysia (Woodrow Asai). Derek Zoolander is known for his signature “Magnum” look and lack of intelligence, which is a big part of the film’s humor.
Owen Wilson was cast as Hansel McDonald, a rising star in the modeling world and Derek Zoolander’s main rival. Although portrayed as laid-back and adventurous, Hansel is equally as dimwitted as Zoolander. Although initially introduced as a competition, he and Zoolander team up to uncover the conspiracy. Zoolander’s satirical comedy pokes fun at the fashion industry and its superficial modeling world.
Stiller and Wilson co-starred alongside two Frat Pack members, Vince Vaughn (as Luke Zoolander) and Will Ferrell (as the main antagonist Jacobim Mugatu). Zoolander also starred Christine Taylor, Milla Jovovich, and David Duchovny. In the 2016 sequel Zoolander 2, Stiller and Wilson reprised their roles. Unlike its predecessor, the sequel was considered a Box Office flop. Released theatrically on February 12, 2016, Zoolander 2 is the last movie that has co-starred Ben Stiller and Owen Wilson as of 2024.
5. The Royal Tenenbaums
Ben Stiller and Owen Wilson joined the star-studded cast of Wes Anderson’s 2001 comedy-drama The Royal Tenenbaums. Ben Stiller was cast as Chas, one of the three Tenenbaum siblings. Chas is a financial prodigy who became a successful businessman at a young age. However, following the death of his wife, Chas became overly protective over his two sons, Ari (Grant Rosenmeyer) and Uzi (Jonah Meyerson). Stiller’s character is marked by a sense of paranoia and anxiety about his children’s safety.
Owen Wilson played Eli Cash, a close friend and neighbor of the Tenenbaums. Eli has always longed to be a part of the Tenenbaum family and is close friends with the youngest child, Richie Tenenbaum (Luke Wilson). All grown up, Eli struggles with drug addiction and his personal insecurities. Both characters contribute to the movie’s family, dysfunction, and redemption themes. The Royal Tenenbaums also starred Gene Hackman, Anjelica Huston, Danny Glover, Gwyneth Paltrow, and Bill Murray. The movie was a critical and commercial success.
6. Starsky & Hutch
Ben Stiller and Owen Wilson were cast in lead roles as the title characters. Todd Phillips’ 2004 buddy cop comedy Starsky & Hutch is a comedic take on the characters from ABC’s classic 1970s TV show. Ben Stiller played David Starsky, a no-nonsense, by-the-book cop, portrayed with a mix of tough-guy bravado and comedic uptightness.
Owen Wilson played Ken “Hutch” Hutchinson, Starsky’s laid-back, easygoing partner. Hutch is more willing to bend the rules, taking a casual approach to solving crimes. Starsky & Hutch plays on their odd-couple partnership, banter, and chemistry. The movie also starred two other Frat Pack members, Vince Vaughn and Will Ferrell, in supporting and minor roles. Starsky & Hutch also starred Snoop Dogg, Jason Bateman, Carmen Electra, and Terry Crews.
7. Night at the Museum
In the Night at the Museum film series, Ben Stiller led the ensemble cast as Larry Daley. His character is hired as a night guard at New York City’s Museum of Natural History. On his first night on the job, Larry discovers the museum exhibits come to life at night due to a magical artifact. Larry helps manage the chaos as the movie progresses and becomes friends with many animated exhibits. In the first film, Owen Wilson, who played a miniature cowboy figure named Jedediah, went uncredited for the role.
Jedediah, who’s part of the diorama exhibit, is known for his tough-guy attitude. He later developed a close, comedic friendship with Octavius (Steve Coogan), a Roman general figure. Jedediah’s rivalry-turned-friendship with Octavius added to the movie’s humor. Ben Stiller and Owen Wilson reprised their roles in the series sequels, Night at the Museum: Battle of the Smithsonian (2009) and Night at the Museum: Secret of the Tomb (2014). Owen Wilson was credited for his role in the sequels. Besides these Ben Stiller and Owen Wilson film collaborations, Robert De Niro is also a frequent collaborator of Martin Scorsese.
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