Ben Stiller was a mainstay of the comedy genre during the 2000s. Wherever you looked, it seemed like the funnyman had a new movie out, with 2005 alone seeing five films released starring Stiller. Dubbed the leader of the "Frat Pack" of comic actors that ruled the 2000s (Jack Black, Vince Vaughn, Owen Wilson, etc.), Stiller seemingly had a hand in every comedy released during that time.
Beginning as a comedian in the '90s, Stiller secured a TV show before graduating into a Hollywood leading man. Beyond just being an actor, Stiller is also an accomplished director. While he has had more than a few misses in his cinematic career, the Emmy winner has been involved in some of the best comedies of the past thirty years while diving into more dramatic territory.
'Your Friends & Neighbors' (1998) RT Score: 77%
A black comedy centered around two couples who are both unhappy in their marriages, Your Friends & Neighbors explores their lives and relationships as they indulge in infidelity. Stiller stars as Jerry, a theater instructor married to writer Terri (Catherine Keener), who is cheating on her with her friend Mary (Amy Brenneman).
While the film follows a cast of unlikeable characters, the screenplay is a treat as it weaves a web of infidelity that entangles all the leads. Critics praised the film for its biting critique of sexual politics, and it holds the honor of being the first reviewed film on Rotten Tomatoes.
'Madagascar 3: Europe's Most Wanted' (2012) RT Score: 78%
The exciting conclusion to the beloved animated series, Madagascar 3, stands as the best entry in the trilogy. After already journeying to Madagascar and Africa, Alex the lion (Stiller), Marty the Zebra (Chris Rock), Gloria the hippo (Jada Pinkett Smith), and Melvin the giraffe (David Schwimmer) find themselves joining a traveling circus as it makes its way through Europe.
While the first two films found plenty of fans among families worldwide, Madagascar 3 was the first to win over critics, with the threequel being one of the better films released by Dreamworks Animation. Though the films are marketed towards children, they offer enough enjoyment to satisfy parents and those young at heart with their colorful visuals and amusing screenplays.
'Brad's Status' (2017) RT Score: 79%
Allowing Stiller to showcase his dramatic chops, Brad's Status focuses on Brad (Stiller) as he helps his son prepare for college while pondering where he has ended up in life. After seeing the successes of his college friends, Brad, who runs a non-profit organization, worries that he has wasted his life.
Though it would have been easy for Brad's Status to fall into the realm of melodrama, its grounded and touching story makes for a relatable tale. Stiller gives a great performance in a role that is a far cry from his more over-the-top characters, and his chemistry with Austin Abrams, who plays his son Troy, is a highlight of the film.
Brad's Status is available to stream on Amazon Prime Video.
'The Royal Tenenbaums' (2001) RT Score: 80%
One of Wes Anderson's best films, The Royal Tenenbaums, possesses the Oscar-winning filmmaker's signature offbeat style and memorable characters. When their father announces he is dying, three adult siblings, each uniquely gifted and successful, reunite and reconnect with the family they have grown estranged from.
Stiller plays the eldest son Chas, a successful businessman and widowed father who has grown overprotective of his two sons after his wife's death. Alongside Stiller, the film features a terrific ensemble cast, including Gene Hackman, Angelica Houston, Luke Wilson, and Gwyneth Paltrow. They are all game-enough to bring Anderson and Owen Wilson's quirky screenplay to life.
'Tropic Thunder' (2008) RT Score: 82%
One of Stiller's most iconic movies and one of the most popular comedies of the past 15 years. Tropic Thunder revolves around a war film set, where its lead actors are dropped into the jungle for authenticity. When a local drug cartel happens upon the prima donna stars, their fake movie becomes very real.
Stiller directs this parody of war films such as Apocalypse Now, which proved to be one of the biggest hits of his career. Along with directing, Stiller stars as Tugg Speedman, a fading action hero seeking recognition for his dramatic acting chops. He is supported by a stacked cast that includes Jack Black, Tom Cruise, and Robert Downey Jr.
'There's Something About Mary' (1998) RT Score: 83%
The film that brought Stiller to mainstream attention where he plays Ted, who, due to a gruesome incident involving his zipper, missed out on taking his dream girl Mary (Cameron Diaz) to prom. Thirteen years later and still in love with Mary, Ted hires a private investigator to track her down.
Ted and Mary hit it off, but as the title says, there's something about Mary, and men begin falling over each other to win her heart. Reminiscent of the gross-out comedies prevalent in the late-'90s and 2000s, the film offers plenty of laughs but has a sweet romance at its core, as Stiller and Diaz share great chemistry as the two love interests.
There's Something About Mary is available to stream on Hulu.
'While We're Young' (2014) RT Score: 84%
Teaming up with Oscar-nominated writer-director Noah Baumbach (Marriage Story), Stiller plays Josh, a documentary filmmaker who, along with his producer wife Cornelia (Naomi Watts), is going through a midlife crisis. A chance encounter with young lovers Jamie and Darby (Adam Driver and Amanda Seyfried) leads to friendship between the two couples, and the youthful exuberance of the younger pair begins to rub off on Josh and Cornelia.
While We're Young is classic Baumbach, an indie comedy with relatable characters, memorable lines, and something to say about love, life, and growing old before your time.
While We're Young is available to stream on Showtime.
'Meet the Parents' (2000) RT Score: 84%
Meeting the in-laws is a daunting experience, made especially more nerve-wracking when your father-in-law is Robert De Niro. When Greg (Stiller) decides to propose to his girlfriend Pam (Teri Polo) at her parent's house, a series of unfortunate events kicks into motion as Greg fails at every turn to impress her family.
Meet the Parents was a surprise hit at the box office and remains one of Stiller's best comedies. The film's star is De Niro, whose comedic turn is a stark contrast to his famous gangster characters. The legendary actor brings the same intensity to his role as father-in-law Jack, which further amplifies the laughs.
Meet the Parents is available to stream on Peacock.
'Flirting with Disaster' (1996) RT Score: 87%
Directed by Academy Award-nominee David O. Russell (Silver Linings Playbook), Flirting with Disaster follows Mel (Stiller), a recent father who never knew his biological parents. Along with his wife Nancy (Patricia Arquette) and a growing list of colorful characters, he sets out on a road trip to find the parents who gave him up for adoption.
Flirting with Disaster offered Stiller one of his first leading roles in Hollywood. It proved to be a hit with critics, showcasing the actor's ability to stay grounded amongst the chaos around him.
Flirting with Disaster is available to stream on Starz.
'The Meyerowitz Stories' (2017) RT Score: 93%
The third collaboration between Stiller and Noah Baumbach, after Greenberg and While We're Young. The Meyerowitz Stories follows the three adult children of Harold Meyerowitz (Dustin Hoffman), a famous artist. The three siblings (Stiller, Adam Sandler, and Elizabeth Marvel) are all dysfunctional in their way, and each struggles to relate to their father while living in his shadow.
The most praised film in Stiller's career, The Meyerowitz Stories gifts roles with depth to normally comedic actors Stiller and Sandler, and both men rise to the challenge. Sandler, in particular, is fantastic, and it is one of his best performances alongside his turns in Uncut Gems and Hustle.
The Meyerowitz Stories is available to stream on Netflix.