ByNicholas Staniforth, writer at
Spewing film-related flim-flam and poppycock when necessary. Follow me @nickstaniforth
Nicholas Staniforth

He’s given us Blue Steel, gone full retard when he shouldn’t have and provided audiences with precisely ten squillion laughs over more than a decade. Now on December 19, he’s set to reprise his role as Larry Daley, the night watchmen of an array of magical museum inhabitants in one of his most successful roles in Night at the Museum 3: The Secret of the Tomb. Whilst it might not be considered his strongest suit (it’s really one for the kids isn’t it?) I’ve collected a list of Stiller’s finest. Some might be favourites, some you may have even forgot about but all of them did the job for me. Take a peek and see which ones made the cut as I compile my personal best of Ben Stiller.

Hal L. - Happy Gilmore

In one of Stiller’s smallest and hairiest roles, his cameo as retirement home manager Hal L. in Happy Gilmore almost steals the spotlight in a time when being funnier than Adam Sandler would actually be a challenge (kids, ask your parents about it).

With a ‘tash as despicable as its owner, Hal turns boiled sweet-guzzling grans and granddads into an efficient and well oiled workforce. Dishing out warm glasses of ‘shut the hell up’ on a whim and charging a fortune for quilts, Hal is one of Stiller’s more off the wall alter-egos that makes for a great watch.

Himself - Extras

Continuing to do some favours for his friends, his appearance in Ricky Gervais’ Extras is one of the highlights of the entire series. In one of the shows early episodes, ‘background artist’ Andy (Gervais) crosses paths with Stiller whilst appearing in the funny man come filmmakers grim-looking war drama.

Unfortunately his efforts to get a line in the film lead to a heated chat with Stiller who ends up coming across as a bit of a star-spangled sod. With his tongue practically cemented in his cheek, Stiller marks up a tally of everything from his box-office successes to the women he’s kissed on-screen. Hey, it still counts…Still counts.

White Goodman - Dodgeball: A True Underdog Story

Sports movies played host to a number of competitive tools that have pushed our heroes to greatness and as a result, made the audience want the same. Johnny Lawrence, Shooter McGavin, Clubber Lang; these are the bad lads that we repeatedly boo and hiss at, and Dodgeball’s White Goodman gets just the same treatment, albeit with the occasional laugh as a result.

With a haircut and carefully combed facial caterpillar to rival Billy Mitchell, White Goodman is that sort of deluded, womanizing, arse pebble that is so arrogant it’s amusing. Making it his mission to wipe the floor with the Average Joe’s from the beginning, Stiller proves he’s good at being bad and makes the head of Globo-Gym’s downfall all the more rewarding.

Ted - There’s Something About Mary

For the most part, Stiller’s career has consisted of nice guys close to finishing last and the first one that still stands up is that of Ted in There’s Something About Mary. As if trying to complete a full conversation with Cameron Diaz as Mary wasn’t difficult enough, the Farrely Brothers manage to build any awkward and highly amusing situation they can throw at him.

Having to fight off both Mary’s personal space obsessed brother as well as her roommates intoxicated dog Fluffy, Ted’s lowest point and highlight is still seeing him dealing with a excruciatingly painful zipper accident. It makes any male wince in agony at the brief sight of squished 'frank and beans' but seeing a group slowly crowd around Ben Stiller’s crotch never gets old.

Derek Zoolander - Zoolander

Everyone loves an idiot and in 2001, Stiller brought one to life that would change both the modelling industry and the comedy world combined. Gifted with being really, really ridiculously good-looking and a novice when it comes to architecture (“what is this? A school for ants?!”), everyone’s favourite male model is easily up there as being one of being Stiller’s best alter-egos.

Whether it’s trying to break away from the evil scheme of killing the prime minister of Malaysia or competing in a walk-off against Owen Wilson’s Hansel, Derek Zoolander struts down a catwalk paved in comedy gold. That long discussed but still yet to be realised sequel needs to happen and needs to happen now.

Tom Crooze - Mission: Improbable

Bringing in the funnies from a different screen for a change, Stiller’s appearance at the 2000 MTV Movie Awards was made all the more amusing with the addition of the very billion-dollar making star he was making fun of. In one of the many great sketches that the award show has delivered over the years, Stiller’s hair-brained stunt double to Tom Cruise, Tom Crooze discusses what it takes to step into the shoes of the Mission: Impossible 2’s leading man. Turns out, it’s a lot of punches to the face.

Going as far to change his name so that it sounds like Tom’s, Stiller’s stupendously stupid stunt man goes on like he knows best for Tom much to the annoyance of those around him. Thankfully, he does have his uses when it comes to stepping into the necessary stunts that Tom just can’t do, by taking any hit sent his way. If you’ve never seen this before take the time out and see what happened before Tom and Ben teamed up for the second time in Tropic Thunder.

Arturo Mendes - Anchorman: The Legend of Ron Burgundy

Continuing to prove that some of Stiller’s finest moments are when he has intense facial hair, his appearance as Arturo Mendes in Anchorman is brief, but like a lot of other cameos in the film equally brilliant.

After Brick leads the Channel 4 news team down a dodgy path whilst shopping for a good pair of slacks, they inadvertently wander into a vicious cock-fight with opposing news channels. History books (and Ron) highlight how things really got out of hand, about the horses and the men on fire and some even being killed with a trident. With every man fighting for his channel, one notable contender happens to be Mendes, a mulleted, moustached low-level anchorman who is cracking whips and taking names. He’s also the first to bail when the law turn up - pussy.

Tugg Speedman - Tropic Thunder

As massively pushed as it was in its build-up to release, Tropic Thunder isn’t regarded by many as Stiller’s strongest performances. Hardly breaking from routine, the funny man once again walks a fine line between likeable lad and village idiot as Tugg Speedman. Now admittedly he might be overshadowed by Robert Downey Jr. as a dude playing a dude, disguised as another dude but that’s not to say he doesn’t have his moments.

Reenacting his panned performance in Simple Jack for some gun-toting and emotional guerrillas, Speedman treads where few actors dare, going full-retard in the name of the art. The real praise might pull away from Stiller’s performance and more his direction in one of the best comedic send-ups of the film industry in years. Brimming with laughs every minute, the film also highlights what sort of scope Stiller can deliver and would eventually go on to do in The Secret Life of Walter Mitty.

Greg Focker - Meet the Parents Series

It might be the Ben Stiller franchise his fans would be least likely to show an interest in, but there’s still something to be said for Greg ‘Gaylord’ Focker in Meet the Parents. Squaring up against one of cinemas acting titans in the form of Robert De Niro and dancing like a chimp as a result, Meet the Parents and Meet the Fockers to a point (let’s not discuss Little Fockers) still stands as one of Stiller’s most successful films to date.

Watching him being caught in the frown of De Niro also makes for mild amusement, with the highlight being that infamous sit down with a polygraph machine. Seriously though now Ben, if you’re going to be in any sequel next make it a Zoolander one will you?


Which is your favourite Ben Stiller role?


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