Ben Stiller’s 10 Funniest Movie Characters

In a movie career reaching back to the 1990s, Ben Stiller has played several hilarious characters. Compared to some of his contemporaries, Stiller’s comedic persona is much less eye-catching. He doesn’t often play loud, splashy characters. Instead, Stiller has portrayed plenty of awkward, lovable losers. He’s also brilliant at playing it straight, allowing another actor to deliver big, zany performances.

Some of Ben Stiller’s funniest performances have created comedy classics, such as Tropic Thunder and There’s Something About Mary. His often understated style doesn’t always get the attention it deserves immediately, but audiences eventually come to realize how important his characters are to their movies. Stilller has been taking some time off from acting in the past few years, but he still has a stellar comedic legacy.

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10 Hal L

Happy Gilmore (1996) & Hubie Halloween (2020)

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Director Dennis Dugan Release Date February 16, 1996 Cast Adam Sandler , Christopher McDonald , Julie Bowen , Frances Bay , Carl Weathers , Allen Covert

Ben Stiller has a minor role in Happy Gilmore, but Hal L is a scene-stealing presence. Stiller has also played memorable cameos in Anchorman 2: The Legend Continues, Tenacious D in the Pick of Destiny, and more movies, but none have been as funny as his abusive carer in Happy Gilmore. Hal runs the retirement home like a sweatshop, exploiting the elderly residents for cheap labor so that he can sell hand-made quilts.

Hal runs the retirement home like a sweatshop, exploiting the elderly residents for cheap labor so that he can sell hand-made quilts.

Ben Stiller was originally supposed to be uncredited in Happy Gilmore, but his character earned a lot of admiration very quickly. Hal L even returned for a scene in another Adam Sander movie, Hubie Halloween. In the Netflix horror-comedy, Hal shows that he is just as cruel and brash as ever. With Sandler confirming Happy Gilmore 2, a lot of fans will be hoping to see Hal one more time.

9 Walter Mitty

The Secret Life of Walter Mitty (2013)

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Director Ben Stiller Release Date December 25, 2013 Cast Ben Stiller , Kristen Wiig , Shirley MacLaine , Adam Scott , Kathryn Hahn , Sean Penn

The Secret Life of Walter Mitty is the most visually ambitious movie Ben Stiller has directed, but it connects on most of its big swings. The story follows a chronic daydreamer who fantasizes about the life that he has always been too afraid to live for himself, preferring to spend his time bouncing between his apartment and his office. The Secret Life of Walter Mitty is adventurous and uplifting in all the right places.

The Secret Life of Walter Mitty
uses humor to make its protagonist more layered and lovable, and it succeeds in both areas.

Walter Mitty isn’t as funny as some of Stiller’s other characters, purely because The Secret Life of Walter Mitty has more on its mind than comedy. Still, he can get a laugh whenever the script calls for it, either as the butt of someone else’s joke or using some genial dialogue. The Secret Life of Walter Mitty uses humor to make its protagonist more layered and lovable, and it succeeds in both areas.

8 Alex

Madagascar (2005), Madagascar: Escape 2 Africa (2008) & Madagascar 3: Europe’s Most Wanted (2012)

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Director Eric Darnell , Tom McGrath Release Date May 27, 2005 Cast Ben Stiller , Chris Rock , David Schwimmer , Jada Pinkett Smith , Sacha Baron Cohen , Cedric the Entertainer , Andy Richter

The Madagascar franchise is bursting at the seams with zany characters, and Ben Stiller’s Alex is one of the more grounded personalities. Between King Julian’s clownish antics and the spy-spoofing penguins, there are enough characters in the Madagascar movies who can get a laugh. The challenge for the four main characters is that they have to be funny while also carrying the plot and providing an emotional core which audiences can relate to.

Alex’s relationship with Marty is both funny and sweet, and Stiller and Chris Rock make a good team.

Alex is a pampered zoo lion who soaks up the love and adulation of the public, but he is quickly pushed out of his comfort zone when his friends drag him outside of Central Park Zoo. He is often funniest as the straight man while Melman panics uncontrollably or Marty bolts off like a ball of energy. Alex’s relationship with Marty is both funny and sweet, and Stiller and Chris Rock make a good team.

7 Larry Daley

Night at the Museum (2006), Night at the Museum: Battle of the Smithsonian (2009) & Night at the Museum: Secret of the Tomb (2014)

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Director Shawn Levy Release Date December 17, 2006 Cast Ben Stiller , Owen Wilson , Robin Williams , Rami Malek , Dick Van Dyke

Ben Stiller is often at his best when he’s surrounded by weird and wacky characters, so the Night at the Museum franchise utilizes his skillset to perfection. Larry Daley initially wants nothing more than to do his job and go home, but he quickly discovers that the museum’s exhibitions spring to life during the night shift, and he has to deal with a rampaging dinosaur skeleton, squabbling miniature figurines, and historical figures who have come to life.

Ben Stiller is often at his best when he’s surrounded by weird and wacky characters, so the
Night at the Museum
franchise utilizes his skillset to perfection.

The Night at the Museum movies each introduce a few more characters for Larry to deal with, as best he can. This supporting cast is stacked with comedic talent, including Robin Williams, Owen Wilson and Steve Coogan. Stiller is hilarious as the constantly exasperated Larry, whether he is in a slap fight with a monkey or chasing Neanderthals across Manhattan. Night at the Museum puts an ordinary character into an extraordinary situation, and this suits Stiller down to the ground.

6 Gaylord “Greg” Focker

Meet the Parents (2000), Meet the Fockers (2004) & Little Fockers (2010)

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Director Jay Roach Release Date October 6, 2000 Cast Robert De Niro , Blythe Danner , Owen Wilson , Teri Polo , Ben Stiller

Although the franchise’s quality dropped off a cliff afterward, Meet the Parents is still a great comedy movie, showcasing one of Robert De Niro’s best comedy performances. He plays the stern, grumpy father of Gaylord “Greg” Focker’s girlfriend, so Greg has to win his approval before proposing. De Niro strikes up a hilarious dynamic with Ben Stiller. He plays his role with the same seriousness as any of his gangster characters.

If
Meet the Fockers
and
Little Fockers
were as funny as the first movie, Greg Focker might have become Ben Stiller’s funniest character of all.

Greg Focker is a bundle of nervous energy as soon as he sets foot in his girlfriend’s parents’ house. He has a habit of saying and doing things which cause a scene, and his attempts to make things better invariably end up backfiring. If Meet the Fockers and Little Fockers were as funny as the first movie, Greg Focker might have become Ben Stiller’s funniest character of all.

5 Ted Stroehmann

There’s Something About Mary (1998)

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Director Peter Farrelly , Bobby Farrelly Release Date July 15, 1998 Cast Cameron Diaz , Matt Dillon , Ben Stiller , Lee Evans , Chris Elliott

There’s Something About Mary starts off by providing some backstory about the characters in their teen years. Rather than using younger actors, Ben Stiller and Cameron Diaz simply play their own roles, but while Diaz barely changes at all, Stiller is given big braces and a terrible, shaggy haircut. This visually sums up his character. Ted Stroehmann is awkward and uncomfortable in his own body.

Ted is constantly making a fool of himself, but deep down he’s a kindhearted guy.

There’s Something About Mary is one of the best R-rated comedies of the 1990s, starting with the excruciating but hilarious scene in which Ted somehow manages to trap his privates in his zipper. Even when he grows up, Ted is just as awkward and clumsy, unintentionally spoiling every chance he gets with Mary. Ted is constantly making a fool of himself, but deep down he’s a kindhearted guy.

4 Chas Tenenbaum

The Royal Tenenbaums (2001)

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Director Wes Anderson Release Date October 5, 2001 Cast Gene Hackman , Anjelica Huston , Ben Stiller , Gwyneth Paltrow , Luke Wilson

See more : Every Eli Roth Movie, Ranked Worst To Best

Ben Stiller’s only collaboration with Wes Anderson produced one of the director’s best movies. Anderson is known for sticking with his performers, including Owen Wilson, Bill Murray and Jason Schwartzman, but new faces can periodically bring their own approaches to his highly stylized works. Ben Stiller isn’t a typical Wes Anderson-style comedic actor, but he is superb in The Royal Tenenbaums.

Ben Stiller isn’t a typical Wes Anderson-style comedic actor, but he is superb in
The Royal Tenenbaums.

Each member of the overachieving Tenenbaum family deals with their unorthodox upbringing in their own way. Chas tries to stick to a highly regimented parenting method for his two boys. He models them after himself, possibly as a way to live vicariously through them to restore his lost youth. Together, they make an odd trio with the same tracksuits and permed haircuts, and the same childish sense of glee when Royal Tenenbaum starts to show them a good time.

3 White Goodman

Dodgeball: A True Underdog Story (2004)

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Director Rawson Marshall Thurber Release Date June 18, 2004 Cast Vince Vaughn , Christine Taylor , Ben Stiller , Rip Torn , Justin Long , Stephen Root

White Goodman is far from Ben Stiller’s typical style of character. While Stiller excels at playing awkward straight men, White Goodman is a loudmouthed gym bro with an immense ego. The character seems ready-made for someone like Will Ferrell or Jack Black who would be more accustomed to playing splashy roles. Stiller is surprisingly effective as the Globo Gym CEO, however, partly because his short statue gives White a hilarious Napoleon complex.

While Stiller excels at playing awkward straight men, White Goodman is a loudmouthed gym bro with an immense ego.

White Goodman wouldn’t be as funny if he were played by a more physically imposing actor. He needs to be the type of character who Vince Vaughn could easily swat away if he wanted to, but White is flanked by much bigger teammates and protected by his immense business empire. His success has inflated his ego to the level that he has an oil painting of himself wrestling a bull in his office, but Stiller injects a hint of insecurity and loneliness into his character. Dodgeball 2 is in development, but it hasn’t been confirmed whether Stiller will return.

2 Derek Zoolander

Zoolander (2001) & Zoolander 2 (2016)

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Director Ben Stiller Release Date September 28, 2001 Cast Owen Wilson , Ben Stiller , Milla Jovovich , Christine Taylor , Will Ferrell

Zoolander is one of Ben Stiller’s funniest and most quotable comedies, pairing him up with frequent collaborator Owen Wilson for a celebrity satire that hits all the right notes. Stiller plays Derek Zoolander, a self-obsessed male model who lives in a world where male models are the hottest celebrities around. He is irredeemably stupid, to the point that he and his friends get into a fun gasoline fight.

Derek’s ego makes his empty-headed actions even funnier. He is surrounded by sycophants who treat him like royalty, so he falsely believes he is intelligent.

There have been countless comedy movies which have tried to get laughs out of how ignorant the characters are, but Zoolander is a cut above most of these. Derek’s ego makes his empty-headed actions even funnier. He is surrounded by sycophants who treat him like royalty, so he falsely believes he is intelligent. Derek Zoolander is also one of Ben Stiller’s best characters because he shares the screen with Stiller’s father. Jerry Stiller plays Derek’s world-weary agent. Sadly, Zoolander 2 didn’t live up to the original.

1 Tugg Speedman

Tropic Thunder (2008)

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Director Ben Stiller Release Date August 13, 2008 Cast Ben Stiller , Robert Downey Jr. , Matthew McConaughey , Tom Cruise , Jack Black

Tropic Thunder has plenty of show-stopping comedic characters, including Tom Cruise’s surprisingly hilarious studio executive and Robert Downey Jr.’s pompous method actor. Tugg Speedman fancies himself as a more grounded Hollywood personality, but he proves to be just as obsessed with success and image as anyone else. Tugg can’t handle being anything other than the hottest actor on the scene.

Since Ben Stiller is also the co-writer and director of
Tropic Thunder,
the character of Tugg Speedman could be seen as his own sly self-parody.

Since Ben Stiller is also the co-writer and director of Tropic Thunder, the character of Tugg Speedman could be seen as his own sly self-parody. Tugg is an actor who desperately craves respect and critical acclaim, but he has been typecast as a vapid action hero. This could be Stiller’s way of poking fun at his own attempts at more serious work, when audiences really want to see him as a comedic actor.

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Category: Entertainment