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The funniest Ben Stiller movies of all time
11 Aug 2025

Ben Stiller has been a staple in the comedy film department, with his one-of-a-kind style and impeccable timing.

Over the years, he has acted in several movies that have had the audience rolling on the floor laughing.

Today, we look at five such iconic comedy movies starring Stiller and talk about their legacy and what makes them special.

'Zoolander' - A fashion satire
Fashion parody

Zoolander, a 2001 release, features Stiller as Derek Zoolander, an exceptionally dim-witted male model.

This film takes a satirical dig at the fashion industry, ridiculing its vanity and superficiality with over-the-top characters and ludicrous plotlines.

It employs humor to criticize fashion, turning into a cult classic for its unforgettable comedic scenes and witty commentary.

'Meet the Parents' - Family comedy
Family dynamics

In Meet the Parents, Stiller plays Greg Focker, who has the misfortune of meeting his girlfriend's family for the first time.

The film hilariously highlights the awkwardness and tension that comes with such a situation.

Released in 2000, it was praised for its relatable humor and stellar performances by the cast. Its success spawned two sequels, chronicling Greg's misadventures.

'Tropic Thunder' - Hollywood spoof
Movie industry satire

Tropic Thunder, which was released in 2008, is an action-comedy film that parodies Hollywood filmmaking conventions.

Stiller plays Tugg Speedman, an actor struggling to revive his career through an ambitious war movie project gone wrong.

The film cleverly blends satire with action sequences while poking fun at various showbiz culture.

Its ensemble cast delivers standout performances, contributing significantly to its critical acclaim.

'Night at the Museum' - Magical adventure
Museum mayhem

In Night at the Museum, Stiller plays Larry Daley—a night guard who finds exhibits coming alive after hours inside New York City's American Museum of Natural History.

The family-friendly adventure-comedy blends fantasy with hilarious situations as Larry struggles through chaotic nights with animated historical personalities like Teddy Roosevelt or Attila Hun.

Released way back in 2006, it gave rise to two successful sequels, continuing this magical journey.

'Dodgeball: A True Underdog Story' - Sports comedy
Underdog triumphs

Dodgeball: A True Underdog Story, which was released in summer 2004, has Stiller as White Goodman, the eccentric owner of a rival gym battling against the Average Joe's Gymnasium team led by Vince Vaughn's character, Peter LaFleur.

The sports-themed comedy is all about underdogs struggling against odds amid hilarious antics on and off the court, and is an absolute riot throughout its runtime.