There are plenty of dynamic duos on the big screen, but few are able to bring in a solid chemistry with great quantity, consistency, and laughs than Ben Stiller and Owen Wilson. They are both considered to be part of the “Frat Pack,” which is a nickname given to a group of comedy actors who have appeared together in several high-grossing comedy films since the mid-1990s. Along with Stiller and Wilson, the group consists of Luke Wilson, Will Ferrell, Steve Carell, Jack Black, Paul Rudd, and Vince Vaughn.
Stiller and Wilson did not start together in show business. Stiller was born to comedians Jerry Stiller and Anne Meara, making his acting debut as a guest on his mother’s short-lived television series, Kate McShane. Wilson, on the other hand, got his start at the University of Texas with his brothers and filmmaker Wes Anderson. The two would appear together in the same film in 1996 and go on to star in 11 more films together. Here are all 12 films with Ben Stiller and Owen Wilson, ranked.
12 Little Fockers
Stylized as Meet the Parents: Little Fockers, Little Fockers is a 2010 comedy film serving as the third and final film in the Meet the Parents film series. The film stars Robert De Niro, Ben Stiller Owen Wilson, Blythe Danner, Teri Polo, Jessica Alba, Dustin Hoffman, and Barbra Streisand. The film takes place five years after the events of Meet the Fockers, where Gaylord “Greg” Focker (Stiller) is preparing for his twins’ fifth birthday party. Things start to go wrong when Greg’s father-in-law Jack Byrnes visits, diagnosed with a heart condition and embittered by his daughter Debbie’s divorce from her husband Bob after he cheated on her with a nurse.
Jack had planned to declare Bob the next head of the Byrnes family, but has decided to instead pass the role to Greg. However, after what happened with Debbie, Jack becomes suspicious of Greg, suspecting him of infidelity. To add to the hijinks, Jack tries to convince Greg’s wife, Pam, to divorce Greg and renew her relationship with her ex-fiancé, Kevin Rawley (Wilson).
11 Zoolander 2
Zoolander 2 is an action comedy film directed by and starring Ben Stiller that was released in 2016, and serves as a sequel to the 2001 film Zoolander. Alongside Stiller, Owen Wilson, Will Ferrell, Penélope Cruz, and Kristen Wiig also star. It was a box-office flop compared to the original film, receiving largely negative reviews and earning $56.7 million against a $50-55 million budget.
The film follows Derek Zoolander (Stiller), a male fashion model, and Hansel McDonald (Wilson), a fashion model who was also Derek’s rival from the first film. The two took a break from modeling and each other but are now dragged back in when a retired swimsuit model brings up recent celebrity deaths. Derek realizes his son who was taken from him is in Rome, so he and Hansel head to Rome where they find the fashion-model legends of “Adam, Eve, and Steve,” and the “Chosen One.”
10 Meet the Fockers
The sequel to the Meet the Parents and the second installment in the series is Meet the Fockers, a 2004 comedy film. Robert De Niro, Ben Stiller, Dustin Hoffman, Barbra Streisand, Blythe Danner, and Teri Polo star, with Owen Wilson, Alanna Ubach, Ray Santiago, Tim Blake Nelson, and Shelly Berman in minor roles. The film follows Greg and Pam as they introduce their respective parents to each other before their wedding. It’s a clash of personality, where Greg’s parents are eccentric, fun-loving, and free-spirited, while Pam’s father is a strict retired CIA operative.
Wilson makes his appearance as Pam’s former fiancé, Kevin Rawley, who is now an ordained interfaith minister who marries Greg and Pam. The film was a box office success, grossing $552 million worldwide against an $80 million budget, with mixed or average reviews.
9 Night at the Museum
Based on the 1993 children’s book of the same name by Milan Trenc, Night at the Museum is a 2006 fantasy comedy film featuring an ensemble cast of Ben Stiller, Carla Gugino, Dick Van Dyke, Mickey Rooney, Bill Cobbs, and Robin Williams. The film follows divorced father Larry Daley to applies for a job as a night watchman at New York City’s American Museum of Natural History. He discovers that the exhibits come to life at night thanks to a magical Egyptian artifact called the tablet of Akmenrah.
Though uncredited in this film, Owen Wilson plays a miniature cowboy figure named Jebediah, who had a rivalry with another miniature figure: Octavius, played by Steve Coogan, of Ancient Rome. Though the film received mixed reviews from critics, it was the fifth highest-grossing film of 2006, with $574.5 million and the highest-grossing film in its opening weekend, with $30.8 million.
8 Night at the Museum: Battle of the Smithsonian
Three years after the original, Night at the Museum: Battle of the Smithsonian released, with Ben Stiller returning in the lead role as Larry Daley. Amy Adams, Owen Wilson, Steve Coogan, Hank Azaria, Christopher Guest, Alain Chabat, Jon Bernthal, and Robin Williams star alongside Stiller. The film takes place three years after the events of the first film, where Larry had left his job as the night guard and started a company selling his own inventions on direct-response television. However, he learns that most of the exhibits will be moved to the Smithsonian Institution archives and replaced with holographic displays, but the Tablet of Ahkmenrah will stay behind, meaning the departing exhibits will no longer come to life.
However, Dexter the monkey brought the tablet to the Smithsonian, as Larry learns from phone call from the panicked miniature cowboy, Jebediah. Ahkmenrah’s older brother, Kahmunrah plans to use the tablet’s power to conquer the world. With Amelia Earhart’s help, Larry took down Kahmunrah and saved the exhibits. Like its predecessor, Battle of the Smithsonian received mixed reviews and was a box office success, grossing $413 million against a $150 million budget.
7 Night at the Museum: Secret of the Tomb
Night at the Museum: Secret of the Tomb is a fantasy comedy film released in 2014. It is the third installment in the Night at the Museum franchise, and the last live-action one. Ben Stiller, Robin Williams, Owen Wilson, Steve Coogan, and Ricky Gervais return, with Dan Stevens, Rebel Wilson, and Ben Kingsley joining the cast. The film sees the exhibits in danger when the Tablet of Ahkmenrah begins corroding, meaning the magic is ending and the exhibits will no longer come to life.
To save the tablet, Larry and Ahkmenrah travel to the British Museum to talk to Ahkmenrah’s parents, Merenkahre and Shepseheret. Tagging along is Teddy Roosevelt, Sacagawea, Attila the Hun, Jebediah, Octavius, Dexter, and Laaa. Like the first two films, Secret of the Tomb received mixed reviews and grossed $363.2 million worldwide against a budget of $127 million, making it the lowest-grossing film in the franchise.
6 The Cable Guy
The Cable Guy is a black comedy film directed by Ben Stiller released in 1996. The film stars Jim Carrey and Matthew Broderick, with Leslie Mann, Jack Black, George Segal, Diane Baker, Owen Wilson, Janeane Garofalo, David Cross, Andy Dick, Stiller, and Bob Odenkirk. It follows Ernie “Chip” Douglas, an eccentric cable installer who becomes involved in the life of a customer, Steven Kovacs.
The Cable Guy serves as the first collaboration between Stiller and Wilson, though neither of them are in a major role. Stiller plays a pair of twins, one of whom murders the other and Wilson plays an unnamed man who went on a date with Steven’s ex-girlfriend and was severely beaten by Chip for his trouble.
5 Permanent Midnight
Starring Ben Stiller, Elizabeth Hurley, Maria Bello, Owen Wilson, Cheryl Ladd, and Janeane Garofalo, Permanent Midnight is an independent drama film released in 1998. It is based on Jerry Stahl’s autobiographical book of the same name, depicting Stiller as Stahl, a successful TV writer and his struggles with substance abuse. As he is approaching the end of his drug rehabilitation program, Stahl impulsively quits his job at a fast-food restaurant when he meets a woman named Kitty through the drive-through window.
The two check into a motel, and he tells her his life story between bouts of sex, which is shown on screen through a series of flashbacks. Upon moving to Los Angeles from New York City, Stahl befriends a fellow addict named Nicky, who’s played by Owen Wilson. Permanent Midnight only grossed $1.1 million in its limited theatrical release in the United States, with mixed reviews from critics.
4 Starsky & Hutch
Starring Ben Stiller and Owen Wilson in the titular roles, Starsky & Hutch is a buddy cop action-comedy film released in 2004, and serves as a film adaptation of the original television series of the same name that ran from 1975 to 1979. The film follows David Starsky and Ken “Hutch” Hutchinson, two streetwise cops in California in 1975 as they bust drug criminals with the help of an underworld boss known as Huggy Bear.
It acts as a sequel to the TV series, showing the beginning of Starsky’s and Hutch’s partnership. Additionally, the film also switches the personalities of the characters, with Starsky being a serious cop and Hutch as laid-back rather than vice versa. Vince Vaughn, Snoop Dogg, Jason Bateman, and Carmen Electra also star. Starsky & Hutch grossed $170 million worldwide against a $60 million budget, though it received mixed reviews (via Rotten Tomatoes).
3 Zoolander
While the sequel ranked lower on this list, the original Zoolander film received generally positive reviews from critics and was a box-office success, grossing $60.8 million worldwide against a budget of $28 million. Released in 2001, Stiller stars as Derek Zoolander, a dimwitted supermodel, and Owen Wilson as Derek’s rival model, Hansel McDonald.
Top people in the fashion industry are hired by other executives to assassinate the Prime Minister of Malaysia because he plans to pass progressive laws that would end up harming their business. Jacobim Mugatu and Derek’s agent Maury Ballstein plan to brainwash Derek into committing the murder since he’s already at the end of his career.
2 The Royal Tenenbaums
Wes Anderson’s 2001 comedy-drama film The Royal Tenenbaums stars Danny Glover, Gene Hackman, Anjelica Huston, Bill Murray, Gwyneth Paltrow, Ben Stiller, Luke Wilson, and Owen Wilson. The film follows the lives of three gifted siblings who experience great success in their youth, but greater failures as adults. The kids’ eccentric father, Royal Tenenbaum, abandoned them when they were adolescents, but returns when they become adults, faking a terminal illness to try and reconcile with them and his ex-wife.
Stiller stars as Chas Tenenbaum, a math and business genius, while Wilson plays Eli Cash, the Tenenbaum’s neighbor and the best friend of Richie Tenenbaum. The film received positive reviews from critics, becoming Anderson’s most financially successful movie until The Grand Budapest Hotel in 2014.
1 Meet the Parents
Meet the Parents is a comedy film released in 2000, and the first in the Meet the Parents franchise starring Robert De Niro, Ben Stiller, Blythe Danner, Teri Polo, and Owen Wilson. The film follows a series of unfortunate events that hapless nurse Greg Focker must endure when he visits his girlfriend’s parents, Jack and Dina Byrnes. Wilson appears as Kevin Rawley, Pam’s ex-fiancé and a wealthy stock investor/carpenter.
The film received positive reviews from critics, often cited as one of the funniest films of the year in which it was released. Within eleven days, the film had earned back its initial budget of $55 million and quickly become one of the highest-grossing films of 2000, earning $330 million worldwide.