Ben Stiller’s Most Iconic Characters, Ranked Worst to Best

By  · Published on February 11th, 2016

One of Ben Stiller’s most iconic characters returns to theaters this week. Derek Zoolander first appeared in a sketch made for the 1996 VH1 Fashion Awards, and Stiller brought the dim-witted male model back to the event a year later before promoting him to the big screen in 2001. Now, 20 years since his inception, he’s finally back with Zoolander No. 2. It’s surprising that such a popular character took so long to receive a sequel, but does he actually deserve one?

Below we look at Stiller’s 15 most well-known roles, ranking them from the worst to the best. And I’ll tell you right now: Zoolander is not that high on the list.

15. Larry Daley (Night at the Museum)

There’s a difference between a straight man and a bland man, and Stiller’s museum security guard in the Night at the Museum franchise is the latter. He’s at the center of his movies, acting as a glue for the main attractions ‐ that’d be all the exhibits that come to life ‐ but he’s like a clear, almost invisible adhesive. Nothing about his part in the series is memorable at all. The majority of people who’ve seen all three installments probably couldn’t even tell you his name.

14. Ted Stroehmann (There’s Something About Mary)

Neither his first nor his best example of the awkward, bad-situation-after-another shtick that he’s become famous for, this is unfortunately one his most commonly celebrated. The Farrelly brothers creation is the most ridiculous of his roles, but not in a funny way. The scenarios he finds himself in aren’t realistic enough, therefore not at all relatable, nor is he an interesting enough character, so not at all identifiable, to make them more than just cheap and stupid gag play.

13. Arturo Mendez (Anchorman: The Legend of Ron Burgandy)


Should Stiller play a Latino character, even in a cameo? Surely there was a funny person of color for the part. But Stiller had to be involved in Anchorman’s Frat Pack-populated rumble, and he loves handlebar mustaches. The biggest problem with this character has nothing to do with race anyway. It’s that he’s just not funny enough, especially for being the leader of the last news team introduced in the scene. His silent colleague with the machete and the maraca, though, is hilarious.

12. David Starsky (Starsky & Hutch)

Stiller may be okay at playing the straight man now and again, but he’s not permitted to be as grounded as he should be as the tough, no-nonsense half of this buddy cop comedy. And he’s often at his worst excessiveness when meant to be a tough guy. The most thought that went into remaking this character from the classic TV series was in his appearance, and to that, the movie is fairly successful. Beyond that, neither the script nor Stiller has anything new to say about this guy.

11. Derek Zoolander (Zoolander)

More than any of Stiller’s roles, Zoolander is the equivalent of a one-note Saturday Night Live character getting his own movie and not really having enough substance to fill a feature. Stiller’s more outlandish creations have always been best in small doses, whether in sketches on The Ben Stiller Show or as minor or cameo roles in other people’s movies. Even then, Zoolander is not a very likable or relatable character and would probably still be irritating in one or two scenes.

10. White Goodman (Dodgeball: A True Underdog Story)

DODGEBALL: A TRUE UNDERDOG STORY, Ben Stiller, 2004, TM & Copyright (c) 20th Century Fox Film Corp. All rights reserved.

As far as thinly developed comedy film adversaries go, Goodman is at least distinct and interesting in his appearance, especially when wearing his dodgeball team uniform. He’s got the look and energy of a funny alpha male type, but the gym-owner character doesn’t bring much to the movie beyond that. None of Stiller’s lines meant for humor hit their mark and his fake commercials are only mildly amusing. The good thing is it’s not a leading role so could be insubstantial.

9. Mr. Furious (Mystery Men)

How funny is a superhero whose power is his rage? No, he doesn’t grow in size and strength, like the Hulk. He just gets mad. His real name is Roy, and he goes mildly berserk when he’s angry, with no additional weapons that are a part of him (a la Wolverine) or not. It’s another character that doesn’t have enough going on to be stretched through a whole movie, but he is sufficiently ridiculous and is surrounded by plenty of other ridiculous heroes, so it works out fine. Just fine.

8. Alex the Lion (Madagascar)


It’s kind of funny to hear Stiller’s voice coming out of an animated lion, one who has almost always lived in captivity in the middle of Manhattan and so doesn’t have a mighty personality. But it doesn’t quite fit. The character needs something a little more regal considering he’s at least still the king of the zoo. The character has also become less interesting and less funny as the Madagascar franchise goes on. For instance, his origin story in Madagascar: Escape 2 Africa ruined the joke about why he lacks savage instincts by revealing that he was just born without a desire to hunt.

7. Reuben Feffer (Along Came Polly)

This is basically his character from There’s Something About Mary done right. Feffer is another one of Stiller’s awkward and unlucky stooges, and he’s even dating a girl he knew from grade school, but he and everything else in the movie are far more genuine and earnest this time around. Still, the guy is pretty simplistically written, the gist of his personality being that he’s not a risk-taker, and eating nuts off the street is all he has to do to show character growth.

6. Tugg Speedman (Tropic Thunder)

Tropic Thunder film within a film
Paramount Pictures

Stiller has played a lot of characters who are famous, most of them with overblown egos. Speedman is a little different, a little more humble than we’d expect from an aging star of blockbusters. Maybe he’s too dumb to be more full of himself, or maybe he just had to be more likable here than usual for the sake of the movie. Along with Speedman comes additional memorable characters, including Simple Jack, who would be ranked very low on this list if he were Stiller’s not Speedman’s.

5. Walter Mitty (The Secret Life of Walter Mitty)

Mitty is like Speedman, only he’s an actor of daydreams and his roles are all in his head. The character itself is a classic type: a man who is the very definition of meek has a wild imagination, through which he gets to be the hero, lover and all-around adventurer he wishes he was in the real world. It worked previously on page and screen, too, but Stiller is the perfect guy to play it again, mixing up straight charm as real Mitty with exaggerated personalities as fantasy Mitty.

4. Gaylord ‘Greg’ Focker (Meet the Parents)


What could have just been a glorified sitcom role is given more depth in the Meet the Parents franchise thanks to Stiller’s rare achievement of the right balance between his straight man and his schlemiel personas. Once again, he’s his own foil due to his character’s combination of clumsiness, discomfort, and inability to be fully honest with others. He had previously done a similar shtick with worse and better results, yet this guy is his most fleshed out as a person, not just as a fool.

3. Mel Coplin (Flirting With Disaster)

While not as worthy of academic analysis as Focker apparently is, Stiller’s original awkward situation comedy role is still much funnier and far more interesting. Being adopted and in search of his biological parents means he can be a blank slate and also try to fit his personality to the various potential mothers and fathers he meets in his journey. And he also manages to just fit perfectly into an ensemble without standing out too much or being invisible.

2. Tony Wonder (Arrested Development)


We were going to limit this list to movie roles, but that meant excluding one of Stiller’s funniest characters. Wonder is one of the few of his excessively portrayed parts that never gets old no matter how often he appears. Not that he should get his own movie. With his w-shaped goatee and “talent” for illusions (and allusions), most involving him making things seem to appear out of thin air, he is a hilarious foil for both GOB Bluth and the reputation of magician as a real trade.

1. Chas Tenenbaum (The Royal Tenenbaums)

Stiller gives his greatest, most endearing performance in Wes Anderson’s film about the dysfunctional Tenenbaum family. Of course, this isn’t a ranking of his work as an actor, but the uncommon emotionality he exhibits in the role helps push it to the top of the ranks. He manages to stand out in an ensemble without resorting to his usual over-the-top tricks. In addition to being extraordinarily played, the character is also his most visually iconic and most richly developed. Partly thanks to two related characters, his two sons. It’s a shame Stiller hasn’t worked with Anderson since.

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Christopher Campbell began writing film criticism and covering film festivals for a zine called Read, back when a zine could actually get you Sundance press credentials. He's now a Senior Editor at FSR and the founding editor of our sister site Nonfics. He also regularly contributes to Fandango and Rotten Tomatoes and is the President of the Critics Choice Association's Documentary Branch.