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Ben Stiller’s 10 Funniest Movies

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Ben Stiller’s 10 Funniest Movies

Ever since becoming one of the biggest stars in Hollywood with hit movies in the late 1990s and early 2000s, Ben Stiller has pretty much had his pick of whatever movies he’s wanted to be in. He has used his powers for good, as he has gotten some of the most gleefully absurdist comedies made over the course of his career. And he’s collaborated with Noah Baumbach on some beautifully contemplative dramedies, too, which have also been hilarious (in a different way, of course). So, let’s take a look back at the 10 funniest movies Ben Stiller ever starred in.

10. The Watch

This sci fi comedy about a neighborhood watch organization that takes on the alien invaders in suburban middle America is not a perfect movie, but it is very funny. The cast of Ben Stiller, Vince Vaughn, Jonah Hill, and Richard Ayoade have terrific comedic chemistry together and bounce off each other hilariously. It’s a shame that this movie didn’t do so well at the box office, because it would’ve been fun to see that cast develop their dynamic in sequels. The movie was originally written to be a PG 13 family movie, but thankfully the studio heads changed their minds and brought in Seth Rogen and Evan Goldberg to revise the script to be a harder R rated affair. Ben Stiller has always mined comedy gold out of being the straight man to Vince Vaughn’s smooth, fast talking, charismatic charmer and this is no different. A lot of critics objected to the use of Costco product placement, but come on. Okay, there are a lot of references to Costco and it’s a major plot point, but there are a bunch of funny jokes about Costco in the script, which in a comedy movie, makes the somewhat shameless product placement seem worth it.

9. Along Came Polly

Ben Stiller is at his funniest when his character is getting screwed over. They say that acting is reacting. Well, Stiller is the master of comedic reaction. In this movie, he gets married to the woman of his dreams and his whole future seems to be set and seems to be perfect – and then she cheats on him on their honeymoon and his life goes into a tailspin. He doesn’t know what to do with himself. Where does he go from here? It’s a great movie. Thematically, the story of an insurance adjuster who always weighs up the pros and cons of things to try to cheat fate into going the way that he wants it to, only to meet the most free and spiritual and liberated and spontaneous woman who ever lived, is surprisingly strong. She teaches him to let loose and be free and he’s a million times better for it. Philip Seymour Hoffman provides fantastic support as Stiller’s character’s best friend, a former child actor who is desperate to reclaim his former glory. This is not Stiller’s finest movie, but he has terrific chemistry with his co star Jennifer Aniston and it is consistently laugh out loud hilarious.

8. Zoolander

If you thought that the vapid world of fashion was too ridiculous to effectively satirize, just wait until you see the absurd heights that Ben Stiller takes it to in his tale of a male model who is brainwashed into killing the Malaysian prime minister to protect child labor. It was the brainchild of comic’s comic Drake Sather. Such gags as the “Blue Steel” look (which is based on Stiller’s then wife Christine Taylor’s observation of the expression that Stiller makes when he looks at himself in the mirror) and the line “What is this, a center for ants?!” make this a truly brilliant comedy. The supporting players like Will Ferrell as Mugatu and Owen Wilson as Hansel – not to mention the endless string of hilarious cameo appearances – make up a terrific cast. It’s not only a hysterical comedy with a consistent stream of jokes and gags that land and get belly laughs, it also has a genuine character arc for Derek Zoolander. As far as comedies go, this is about as funny and as smartly written as they come. Unfortunately, the belated sequel in 2016 did not live up to the legacy of the original, but then what could?

7. The Meyerowitz Stories

The last time we saw Adam Sandler and Ben Stiller on screen together before this movie, Stiller went uncredited as the nursing home employee who was abusing Sandler’s character’s dear old grandma. This contemplative comedy drama from writer and director Noah Baumbach is a vastly different project, but an equally great one. Sandler and Stiller play half brothers, the latter of whom he gave much more attention than the former. Their dynamic is summed up perfectly in a scene set in the hospital where their shared father is dying. They walk through the hallways, catching up, and they never seem to be on the same page. It’s a scene that is both brilliantly written and brilliantly acted, which pretty much encapsulates the quality of the film as a whole – Stiller and Sandler have fantastic chemistry that it would be great to see more of in the future. Out of the handful of films that Ben Stiller and Noah Baumbach have collaborated on together, this Netflix exclusive bought off the festival circuit is the funniest and most emotionally charged one. Let’s hope that Stiller and Baumbach continue their working relationship and bring us a bunch more beautifully human stories like this one.

6. The Heartbreak Kid

This is such an underrated gem. The Farrelly brothers teamed up with Ben Stiller once again for the story of a man who meets his true love while he’s on his honeymoon with the woman he thought was his true love but has turned out to be a total nightmare. There are plenty of great supporting actors in this movie, from Scott Wilson (better known as Hershel Greene) to Ben Stiller’s own father Jerry Stiller, but the true scene stealer is Danny McBride. Every word that comes out of that guy’s mouth in this movie is absolutely hysterical. That scene where he stuffs a pepper up Ben Stiller’s nose after finding out that he’s been married this whole time could’ve easily been a silly slapstick moment, but McBride and Stiller elevate it to a level of comedy gold that is virtually unparalleled. The narrative is actually interesting, as it takes surprising twists and turns and is always moving to create conflict and obstacles and tensions for the characters, as well as being hilarious. Stiller sneaking across the border after losing his ID is a highlight. The ending of the movie is perfect, too, as it brings the whole story full circle and starts the cycle over again.

5. The Royal Tenenbaums

Years before he would become the go to star for Noah Baumbach’s movies, Ben Stiller was working for another brilliant auteur with a unique creative voice. This was the quirky story of a dysfunctional family that hit the big screen long before the Bluths hit the small screen. Stiller, playing an even more psychopathic version of fitness guru White Goodman here, is just one key component of a terrific ensemble cast that is anchored by Gene Hackman as Royal Tenenbaum and helped by stellar turns from Gwyneth Paltrow and Luke Wilson. The humor in this movie is not for everybody, as its comic sensibility is absurdist and ironic and at times a little dark, but one thing that no one can accuse this movie of being is unoriginal. It is one of the most fiercely original movies ever made and established Wes Anderson’s visual directorial style as that of a novel told on film. As with all of Anderson’s work, the influences here are literary – everything from J.D. Salinger to Cormac McCarthy – but it works brilliantly as a visual cinematic piece. This melancholic family tale still stands as one of Anderson’s most outstanding works to this day, and probably always will.

4. Meet the Parents

We take a lot of the gags in this movie for granted these days, since the rewatchable nature of the movie has meant that we’ve all seen it so many times that we know what to expect. But the idea of a guy being given a lie detector test by his girlfriend’s father is so rich with comedic potential. A lot of lazier comedies would think that the idea is enough and botch it, but with Ben Stiller and Robert De Niro, it is just as tense and painfully awkward and hysterically funny as it promises to be. The movie’s comedy ranges from cringe comedy like the dinner scene with Greg’s prayer and the broken urn and the line “I have nipples, Greg – could you milk me?” to slapstick comedy like the burning of the wooden, hand whittled altar. A lot of movies struggle to nail just one style of humor, let alone find a balance between a few styles of humor, but this movie does it. Every joke, every scene, every gag lands. All of the actors are perfectly cast in their roles, particularly Stiller and De Niro alongside each other as adversaries. It’s just a shame that the sequels never quite lived up to it.

3. There’s Something About Mary

Who says romantic comedies have to suck? Most of the time, they do, sure, and the problem is usually that there is more focus on the romantic side of things than the comedic side of things. And even then, the romance is formulaic and trite and, well, Hollywood. But when the Farrelly brothers made a romantic comedy with their style of humor, you could bet that it would have more focus on the comedy – and grossout, wacky, absurdist, and/or slapstick comedy at that – and it would be hilarious. Plus, the romance is less formulaic and more interesting to watch, as several men obsess over the same woman. This is one of the most popular and highest grossing comedy movies of all time, with a worldwide gross of over $300 million – and it deserved every penny! Ben Stiller is fantastic in the lead role, from his first scene as a teenager with his balls caught in his fly to the hitchhiker orgy scene to the dog fight scene to the final moments of his romance with Mary. Cameron Diaz proves to be a terrific comic foil opposite Stiller and it’s a shame that we never got to see their dynamic alongside each other again.

2. Tropic Thunder

Ben Stiller grew up as the son of an actor and then became a movie star in his own right, and so he has spent his entire life in the Hollywood fold. So, who better to satirize the film industry and poke fun at the vanity of Hollywood actors than him? Stiller writes, directs, and stars in this hilarious comedy about some actors in a war movie who end up unwittingly getting involved in an actual battle. Stiller based the movie on his experiences on the set of a war movie, where he saw the actors become all smug after shooting it as if they had been a part of an actual military unit in an actual war. There isn’t any dead weight in the brilliant ensemble cast of actors: Ben Stiller, Jack Black, Robert Downey, Jr., Steve Coogan, Danny McBride, Bill Hader, Nick Nolte, Matthew McConaughey – and last but not least, Tom Cruise as a balding, foul mouthed, big handed studio executive. Stiller’s direction, writing, and acting in this movie are all on point – it has the feel of a passion project and it’s an idea that could’ve easily been botched in the execution, but Stiller pulled it off spectacularly.

1. Dodgeball: A True Underdog Story

There’s no question that this is Ben Stiller’s best movie. It’s one of the most original and uniquely funny and smartly written comedies ever made. The absurdist humor – from the guy who’s convinced he’s a pirate to the random appearance of Chuck Norris as one of the judges in the dodgeball tournament – is some of the funniest ever put on film. “If you can dodge a wrench, you can dodge a ball.” It’s also one of the most endlessly quotable comedies ever made. The movie also offers us one of those rare chances to see Ben Stiller in the role of a villain. When he’s playing the good guy, Stiller is always a likable and relatable everyman who reacts accordingly to the absurdity around him. But when he’s playing a bad guy, like the abusive nursing home employee who terrorizes Happy Gilmore’s grandma, he relishes the opportunity to play a terrible guy. That’s what White Goodman is. He’s not only a pitch perfect satire of so called fitness gurus – he’s also a hilarious asshole. He’s the kind of character that would go on to make Adam Scott a star. So, with all of these things combined, this is by far Ben Stiller’s finest hour.

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