15 Ben Stiller Roles for the Comedy Hall of Fame

Despite being the son of comedy legends Jerry Stiller and Anne Meara, Ben Stiller has never fit the mold of what is now considered a Nepo Baby. He has spent nearly three decades carving out his own identity as an actor, writer and director, with the result being a treasure trove of creative street cred. In front of the camera, he’s able to steal scenes with even the most minuscule of moments; behind it, Stiller has consistently been ahead of the curve, with the dystopian workplace series Severance serving as the latest feather in his cap. But despite successful detours to drama, Stiller’s heart always seems to drift back to comedy.

And it’s that aspect of Stiller’s career we’re celebrating today by inducting these hilarious Stiller moments into the Comedy Hall of Fame…

15 Mystery Men

Stiller led an all-star cast in this overlooked 1999 superhero spoof as Mr. Furious, whose superpowers stem from his boundless rage and the butchering of common expressions.

14 Your Friends and Neighbors

Stiller’s performance in Neil LaBute’s 1998 pitch-black sex comedy makes this list simply because it’s so far removed from the over-the-top wacky characters he is typically known for. A dark role in a film full of characters you’re not meant to like, there are numerous subtle notes here that Stiller absolutely nails.

13 Meet the Parents

This is the first of what we like to call the “Ben Stiller really should’ve stopped after the first one” trilogy, along with Zoolander and Night at the Museum. If you disregard the sequels, Meet the Parents is still a solid comedy, largely due to Stiller’s ability to play up the wackiness without overplaying his hand.

12 Zoolander

Easily his most famous character, most fans aren’t aware that Stiller originally created Derek Zoolander for a sketch at the 1996 VH1 Fashion Awards.

11 The Ben Stiller Show

Although it only ran for 13 underappreciated episodes back in 1992, the talent pool on this show was full of future household names.

10 There’s Something About Mary

The Farrelly brothers have been coasting for two decades off the hilarity of Stiller’s testicular trauma.

9 Zero Effect

With the glut of modern-day reimaginings of Sherlock Holmes in recent years, Jake Kasdan’s 1998 Zero Effect was ahead of its time. Loosely adapted from Sir Arthur Conan Doyle’s Holmes novel A Scandal in Bohemia, Stiller plays the Watson-esque assistant to Bill Pullman’s misanthropic, frustratingly quirky “world’s greatest detective” Daryl Zero.

8 Happy Gilmore

The evil emanating from Stiller’s orderly character Hal (and his epic mustache) steals every second of his underused screentime.

7 Greenberg

Another dark-horse candidate for the list, Stiller’s character is incredibly difficult to like but is so pitch-perfect that it’s impossible to picture anyone else playing the role.

6 Night at the Museum

We didn’t want to enjoy this movie when it came out, but it turned out to be a solid excuse to turn down the dimmer switch on our brains and appreciate 90 minutes of some good old-fashioned slapstick.

5 Flirting With Disaster

Stiller plays a man on a cross-country trip to meet his biological parents along with his wife and his hot mess of a social worker in this 1996 film.

4 Tropic Thunder

Stiller pulled off one of the biggest F-yous to everything wrong with Hollywood, and it became among the most celebrated comedies of his career.

3 Dodgeball: A True Underdog Story

Throwing all subtlety out the window, Stiller became the kind of slimeball you need to see nailed in the face with a dodgeball.

2 Next of Kin

Though technically not a comedy, we felt the need to include it since everything about this film, from Patrick Swayze’s ponytail to Liam Neeson’s cringey attempt at a hillbilly accent, dives deep into the pool of unintentional comedy. But it’s all eclipsed by Stiller’s early role as the big, bad gangster’s son, which we could best describe as an Oops! All Fredos version of The Godfather.

1 The Royal Tenenbaums

It’s an uphill battle to stand out in a film with a murderer’s row of talent absolutely nailing it, but Stiller’s turn as the neurotic, track-suit-wearing, overprotective parent, business genius of the Tenenbaum clan did just that.