Best Ben Stiller Roles, Ranked

Summary

• Ben Stiller’s versatile career as an actor and director spans iconic comedies such as Zoolander and dramatic thrillers like Severance.
• Stiller excels in various roles, from comedic leads to villainous antagonists, showcasing his range and talent in Hollywood.
• Through memorable characters like White Goodman and Derek Zoolander, Stiller has cemented his place as a comedic legend in the film industry.

Between the engrossing finale of Severance season 1 and its latest season, the Apple TV bonanza has elevated itself to one of the premier shows of its era as Mark Scout and his coworkers fall deeper into their employers’ deep, dark secrets at Lumon. Among the trials and tribulations the MDR endures, their Outies have become more curious and suspicious of their supposed work, leading to a second season enshrouded in mystery and hostility.

Despite not starring onscreen, the versatile and multitalented Ben Stiller is Severance’s leading director, acting as one of the faces of the transformative show. Known for being a big-budget comedic leading man and director, Stiller has had a career very few can aspire to achieve. His vast catalog of intriguing and hilarious roles in stand-out movies propelled Stiller to Hollywood stardom.

10

Larry Daley — Night at the Museum (2006)

The Voice Of Reason In A Fun Fantasy Setting

In what would later spawn a trilogy of films, Night at the Museum emerged as an entertaining, family-friendly fantasy movie that saw Stiller as an anchor for all the hilarious shenanigans that occur while operating as a security guard at a historical museum. After Stiller’s Larry Daley is hired to do night shifts at an American museum in New York, animals, artifacts, and historical figures in the museum all come to life at night. Chaos ensues, as the famed figures bring the best out of a down-and-out Larry.

Praised for its fresh concept and fun-filled story, Stiller’s bumbling comedic approach evolves throughout Night at the Museum, with his character’s self-belief and care for his job coming to the forefront.

9

Greg Focker — Meet The Parents (2000)

A Love-Hate Relationship With Potential Father-In-Law

Operating opposite Hollywood heavyweight Robert De Niro, Stiller’s starring role as Greg Focker in the quintessential 00s comedy Meet the Parents further established Stiller as a comedic leading man. Seeking to marry his girlfriend, Greg goes to meet his potential in-laws. However, he gets off on the wrong foot with the stern Jack Byrne, his girlfriend’s father, causing a rift that makes Greg’s plan of proposing even harder.

Brimming with anxiety, awkwardness, and embarrassing scenes, the struggle Greg goes on as he tries to appease his future family is an entertaining journey. Stiller and De Niro’s toxic back-and-forth has since cemented itself as an iconic cinematic moment.

8

Hal — Happy Gilmore (1996)

Small Comedic Cameo That Became One Of The Cult Classic’s Many Memorable Moments

Despite only having a tiny and uncredited cameo in Happy Gilmore, Stiller steals the show even alongside the caliber of talent in the comedic golf flick. Happy Gilmore focuses on the journey of Happy, a hockey-turned-wannabe-golfer with a wicked swing who joins the PGA Tour to help keep his grandmother’s home.

While the cult classic gave Adam Sandler a breakout role, Stiller’s appearance as care home worker Hal is undeniably amusing. Stiller’s pushy behavior towards the elderly in his care and attempts to keep it secret from Happy makes the actor’s performance memorable, despite his lack of scenes.

7

Chas Tenenbaum — The Royal Tenenbaums (2001)

Stiller Excels Among An Impressive Ensemble In This Quirky Dramedy

In the movie that shaped Wes Anderson’s future work, The Royal Tenenbaums brought a freshness and eccentricity that audiences yearned for at the start of the 21st century. The chaotic story examines the eclectic Tenenbaum family, who all unite under one roof after the father of the family begins to deal with significant health problems.

Stiller’s Chas Tenenbaum worked as a financial guru and whizkid in his youth. However, following his wife’s death in a plane crash, Chas becomes paranoid in adulthood, hoping to instill his beliefs into his two young sons, who follow his blueprint of life to the letter. Among a selection of masterful comedic performances, Stiller’s Chas thrives with Anderson’s specific and unusual direction.

6

Tony Perkis/Tony Perkis Sr. — Heavyweights (1995)

Underrated Role As A Crazed Fitness Instructor

Often overlooked in Stiller’s and Disney’s catalog is Heavyweights, the 90s flick that lets Stiller have plenty of fun and room to maneuver in dual roles. Heavyweights see a group of overweight children arrive at a camp intended for fun and weight loss. However, its instructor, Tony Perkis, tries to ruin the children’s experience with his wacky and extreme measures.

Featuring stellar child acting performances from some notable names, the movie thrives partly due to Stiller’s vicious and ludicrous performance as Perkis. He acts as the heart and soul of an undervalued movie that produces one of the actors’ most captivating roles.

5

Ted Stroehmann — There’s Something About Mary (1998)

Stiller Fights For The Love Of His Life In A Rom-Com Classic

One movie that pushed Stiller to further stardom was his starring role opposite Cameron Diaz in There’s Something About Mary. The movie stood out in the 90s, an era that saw the rom-com genre run riot. In an attempt to reunite and connect with his high school sweetheart, Stiller’s character Ted Stroehmann finds himself competing with several men for Mary’s affection.

There’s Something About Mary’s performances carry much of the movie’s momentum, particularly with Stiller’s awkward demeanor in pursuit of his dream girl. The role helped boost his rise as a comedic leading man.

4

Tugg Speedman — Tropic Thunder (2008)

A High-Profile Actor Filming A Blockbuster Gone Wrong

Famed for its outrageous story, setting, and characters, Tropic Thunder is a controversial comedy that sees Stiller directing and playing the leading role. Tugg Speedman is a declining movie star who tries to get his film career back on track. Alongside other fictional big-name actors, Speedman starts filming a high-profile movie in Vietnam, eventually resulting in the local mafia taking Speedman hostage. Meanwhile, the film’s production becomes a frenzy as death, ego, and rivalry take center stage.

Competing with an intense performance by Robert Downey Jr. and an ego-ravaged Jack Black, Stiller’s chemistry and dramatic chops with his costars make Tropic Thunder flourish. The variance in his portrayal fits with the absurd narrative told in the classic comedy.

3

Walter Mitty — The Secret Life Of Walter Mitty (2013)

A Boring Guy Goes On The Adventure Of A Lifetime

Starring in and directing a big-budget Hollywood adventure flick rarely happens. However, Stiller took on the task with The Secret Life of Walter Mitty, an adventure-riddled narrative that sees his character of Walter Mitty evolve and transform from a boring wallflower figure to a full-of-life individual. The story follows Walter, a dull Lifestyle magazine employee who goes on an adventurous journey to secure an elusive image from his long-time photographer set to be published in the magazine’s final print issue.

Starting the movie as a generic man, Walter’s long-winded journey sees him come out of his shell, with Stiller’s transformation encapsulating the story’s heart and essence. A particular highlight in The Secret Life of Walter Mitty is his troubled relationship with Ted Hendricks, a digital manager portrayed by his Severance collaborator, Adam Scott. Walter’s gradual shifting attitude towards Ted eventually sees him standing up to his authoritarian rule, showing the protagonist’s heroic development.

2

White Goodman — Dodgeball: A True Underdog Story (2004)

Vain Dodgeball Pro That Sees Stiller Lose Himself In Ludicrous Role

One of Stiller’s few villain roles came in the form of White Goodman in Dodgeball: A True Underdog Story, as his intense rivalry with Vince Vaughn’s character created a sports comedy for the ages. In the film, the protagonist Peter and fellow gym members create a dodgeball team to help secure funds to keep their gym alive. The group enters a high-stakes dodgeball tournament in Las Vegas, where the narcissistic Goodman awaits.

While many excel, Stiller steals the show as an enigmatic antagonist, displaying plenty of showmanship and arrogance that make his performance iconic and electrifying.

1

Derek Zoolander — Zoolander (2001)

Eccentric Runway Model That Has An Intense Rivalry

Zoolander’s impact on pop culture and society has been very apparent. A lot of its iconic status results from Stiller’s shocking performance as the exuberant Derek Zoolander, a now iconic character made famous by the actor in the cult classic. Set in the world of runway modeling, Zoolander’s rivalry with Hansel McDonald sees the former star of the runway attempt to assassinate the President of Malaysia in hopes of rejuvenating his floundering career.

Stiller’s over-the-top and playful persona of Zoolander has become such a staple for the actor. Memes playing on Zoolander’s pizzazz have helped build the character’s legacy, even leading to a sequel based on Stiller’s now-legendary comical exploits.