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Ben Stiller's Funniest Roles, Ranked

Ben Stiller is the perfect antidote to a truly shitty day. When it’s cold, wet and glum and you wish you could spend the whole day in your pajamas. Or when you come home in the evening with a headache just to realize the fridge is empty, and that nobody has liked the Facebook update you posted in the morning. Yeah, Ben Stiller can fix even that precarious situation. We have put together a list of Stiller’s go-to comedies that will make you laugh your pants off, and forget about all your real-life problems.

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7 There's Something About Mary

By all accounts the 90s raunchiest comedy, There's Something About Mary has Farrelly Brothers written all over it. Even if you have never watched Mary before, I bet you are familiar with Cameron Diaz’s “gel” hair GIF, right? The movie starts when gormless high-school student Ted (Ben Stiller) accidentally getting his penis stuck in his zipper in the bathroom of Mary, his stunning prom date. (Cameron Diaz) Ted suffers unfathomable humiliation, and after being carried to the hospital loses contact with Mary. Thirteen years later he decides to track her down by hiring a feckless private investigator, played by Matt Dillon. Chris Elliot also co-stars as Ted’s married best bud, who delivers the movie’s most epic line: “Here you've been in therapy, you know, thinking you blew it with the greatest girl ever, and really it turns out that getting your dick stuck in your zipper was the best thing that ever happened to you.”

6 Zoolander

Ben Stiller in Zoolander

Granted, Zoolander 2 didn’t live up to our expectations. But that happened partly because the original Zoolander had set the comedy bar really high. Back in the day when hapless narcissists were the stuff of comedy, three times male model of the year Derek Zoolander loses his crown by fierce rising star Hansel. (Owen Wilson) Things get even worse when his model friends get killed in a stupidity accident at a gas station.

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Heartbroken, the world’s most beautiful male model then decides to quit modeling. But fate has other plans. Zoolander is a movie directed by Ben Stiller.

5 Meet The Parents

Robert De Niro in Meet the Parents

When you put Ben Stiller and Robert DeNiro in the same story as two diametrically different characters, it’s laughs guaranteed. The unfortunately named Gaylord “Greg” Focker (Ben Stiller) is an easy-going, nice guy who just wants to get along with everyone. This includes his fiancé’s parents, whom he is about to meet for the first time. But as it happens usually, the nicer he tries to be, the nastier his paranoid former CIA father-in-law, Jack, gets. Greg just needs to learn how to stand up for himself and put Jack Byrnes (played by DeNiro) back to his place. But until he gets there, the movie is just an agonizing and embarrassing parade of social gaffes hilariously performed by a team of exceptional comedians.

4 Meet The Fockers

Gaylord Focker’s shenanigans in Meet The Parents were just too good to be spared of a sequel. Comedy sequels seldom live up to the greatness of the original movie, but Meet The Fockers comes pretty close. As if having a complete jerk for father-in-law wasn't enough, now Greg needs to suffer another round of humiliation when he introduces his in-laws to his former hippie parents. (played by Barbra Streisand and Dustin Hoffman). Traumatized by their obsolete flower child parenting, Greg needs to strike a balance between the two couples of radically different mindsets, who also happen to be headstrong baby-boomers. Jack Byrnes, his former CIA agent father-in-law has the most memorable line in the movie when he corners Greg in the changing rooms and threatens him: “All right. Now look, Focker, I'm a patient man. That's what 19 months in a Vietnamese prison camp will do to you. But I will be watching you, studying your every move. And if I find that you are trying to corrupt my first born child, I will bring you down, baby. I will bring you down to Chinatown.”

3 Along Came Polly

Ben Stiller and Jennifer Aniston in Along Came Polly

Ben Stiller is Reuben Feffer, a guy whose wife cheats on him on their honeymoon with her nudist scuba diving instructor. Reuben travels back home alone, feeling like a total washout when he accidentally bumps into Polly, a former schoolmate who works as a waitress. (Jennifer Aniston) Along Came Polly borrows the same romantic mishap storyline that we saw in There's Something About Mary (albeit a much more toned-down and mainstream version of the Farrelly Brothers obscenity).

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There’s nothing wrong with that, because of the strong comedic chemistry between the two main protagonists. Both Stiller and Aniston are exceptionally talented comedians, and the movie delivers 100% feel-good fun.

2 Tropic Thunder

Ben Stiller directs on the set of Tropic Thunder.

In this obvious Rambo parody which he also directed, Ben Stiller does what he knows best, a blunt satire. Just grab your mega-sized popcorn and find your Couch potato favorite spot without overthinking how politically incorrect and offensive the movie is. (If you take it seriously, that is.) You don’t have to tell anyone that you almost choked on your spit from laughter. If anyone asks the next day, you were watching Pearl Harbor, and not Robert Downey Jr in blackface, alongside cigar-smoking children, and the liberal use of the R-word. The “never go full retard” scene sparked a widespread uproar in 2008 when it was filmed, and perhaps Ben Stiller wouldn’t have survived today’s relentless panning on social media. Tropic Thunder is a historical moment in satire that we might never get the chance to recreate.

1 Starsky and Hutch

2004 must have been a very busy year for Ben Stiller and Owen Wilson because they starred together in two comedies, that are both listed here. The Meet The Fockers success was followed by Starsky and Hutch, among others. Recreating the iconic 1970s series, (which I am sure many people have never watched) Stiller and Wilson are the ultimate buddy cops. Two very different characters who are forced to work together, they initially hate the idea. But guess what, they eventually end up being inseparable, brought together by a series of coincidences and a healthy dose of 70s tackiness. Starsky and Hutch take you back to a time in TV history you’d rather not explore without clutching on a bucket-sized ice-cream. More celebrity eye candy in the movie include Vince Vaughn, Snoop Dogg, Juliette Lewis, and Carmen Electra. Pure bliss!

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