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Best And Worst Ben Stiller Movies

Ben Stiller, he's an American comedy mainstay and a Hollywood renaissance man. He writes, directs, acts, and produces. As a result, he's a defining figure in some of the best and funniest movies to grace the screen in the past few decades ... but he's also a leading man in some of the biggest flops.

After all, Stiller is a comedy genius and a great artist, and every artist takes risks. And for Ben Stiller, many of those risks have paid off and rewarded audiences with lovable, memorable cinematic experiences. Other times, those risks have left Stiller falling flat on his face and losing money at the box office. But despite the lows, this brilliant comedian has always managed to brush himself off, get back up, and keep us laughing.

Of course, with his spotty track record — full of both gems and bombs — which Stiller movies are truly great, and which ones are truly terrible? Well, if you want a primer before preparing a comedy marathon, get ready, because we've got the rundown on the best and worst Ben Stiller movies.

Best: Greenberg features one of Ben Stiller's finest performances

This one is probably one of the more controversial entries on the list, but the critical acclaim is undeniable. Greenberg was released in 2010 and proved that Ben Stiller has the acting chops, in addition to the comedy cred, to carry a movie as leading man.

A film by Noah Baumbach, Greenberg follows Stiller as the titular character, Roger Greenberg, a guy who's spending time at his brother's house after a stint in a facility following a nervous breakdown. Along the way, he finds himself drawn into new relationships and old feuds as he confronts the mistakes and frustrations that haunt him. As this is a Baumbach film, it's filled with the director's signature realistic pacing and heartbreakingly intimate portraits of people coming to grips with lives that didn't turn out how they imagined.

Capturing that particularly Los Angeles ennui and balancing it with a script filled with dark laughs is also a hallmark of many a Noah Baumbach film, and Ben Stiller's gravely funny acting fits the tone perfectly. The vulnerable, complex character he portrays and his chemistry with indie darling Greta Gerwig made this movie a hit with critics. Some audiences didn't exactly feel the same way, and most moviegoers certainly didn't return to theaters again and again to see it. But hey, money isn't everything. Even though this movie lost cash at the box office, many view Stiller's performance in the film as one of his very best.

Worst: The Watch is a sci-fi flick that just doesn't work

Over the years, Ben Stiller has begun to stray from traditional slapstick comedy and wacky characters. Audiences have noticed him getting, well, pretty frickin' jacked and gearing towards more action comedies. The Watch, released in 2012, was one such attempt.

The premise is a ton of fun, as a ragtag neighborhood watch uncovers an alien conspiracy in their quiet suburban town. But the execution ... doesn't play. For one thing, even though the movie was released in 2012, it's basically a big boys' club, as the only plot lines for women either revolve around them desperately wanting children, being saved from sexual assault, or being a verbally abused mother. Evidently, the creators of The Watch could envision a world full of aliens, but they weren't able to realize that female characters can exist outside of the context of their reproductive organs.

Worse still, it just isn't funny, as it lazily relies on an overabundance of raunchy humor. Granted, there's a great cast alongside Ben Stiller. Jonah Hill, Richard Ayoade, and Vince Vaughn play the guys in the neighborhood watch, but their chemistry and comedy chops just aren't enough to save this failure of a film. Both critics and fans despised the movie, and honestly, the scathing reviews are funnier than the script.

Best: Zoolander is one of Ben Stiller's wildest comedies

Sometimes, the critics get it wrong. And a movie is much more than the awards it wins or the number of stars it earns from some snobby reviewer sitting in an ivory movie tower. A truly great movie will stick with its audience, even decades later. And 2001's Zoolander is that kind of movie. A goofy send-up of the fashion world and all its overblown, stuffed shirt inhabitants, Zoolander has an all-star cast and is packed with fun cameos.

Ben Stiller as Derek Zoolander and Owen Wilson as his rival turned ally, Hansel, are two top models vying for the public spotlight. When a shadowy cabal of fashion elites tasks designer Mugatu, played by Will Ferrell, with assassinating a world leader, the two airhead models become involved in a plot that's way, way over their heads. Along the way, we're treated to some hilarious appearances from David Bowie and Billy Zane, as well as stars like Heidi Klum, Natalie Portman, and Winona Ryder. Plus, diehard Ben Stiller fans might notice that his wife at the time, Christine Taylor, is playing skeptical reporter Matilda Jeffries, the smartest one in the room.

And yeah, as we mentioned, critics didn't love the film, but audiences did. Popping up in gifs, memes, and any time anyone says the name "Hansel", Zoolander is now engraved in the hearts and minds of Ben Stiller fans everywhere as one of his all-time best films.

Worst: The Marc Pease Experience is just a bad experience

This one you may have never heard of, and honestly, that's probably for the best. The Marc Pease Experience was released in 2009 and stars Jason Schwartzman, Anna Kendrick, and of course, Ben Stiller. Surprised you've never heard of a movie with these three big name actors? Well, after reading the scathing reviews, you'll understand why

The film follows singer Marc Pease (Schwartzman) who's haunted by a high school musical disaster. As a result, he's unable to let go of his childhood and fully take the steps to embracing life as an adult. As for Stiller, he plays a high school teacher having an affair with a student (Kendrick), while also serving as the part-nemesis, part-helper to Scwhartzman's character. But unfortunately for everyone involved, The Marc Pease Experience was more like a very unpleasant experience. Roger Ebert wrote that, "It's badly written and inertly directed, with actors who don't have a clue what drives their characters," while critic William Goss added, "No character is worth caring about, worth pitying, worth paying attention to."

But perhaps critic David Hiltbrand summed it up best when he wrote, "A bad movie about cheesy a cappella and awful musical theater. What could be more excruciating?" And it seems even Paramount Studios knew they had a bomb on their hands. The movie was only released on a very limited basis, which is often what studios will do with a film that they're legally obligated to put in theaters, but they'd rather keep it quiet.

Best: Night at the Museum is a delightful Ben Stiller adventure

Night at the Museum features Ben Stiller as a down on his luck but good-hearted guy starting a new job as the night watchman at the Museum of Natural History. However, he soon finds that when the museum shuts down, the exhibits — from taxidermied lions to Wild West dioramas to the fossilized remains of a T-Rex — come to life!

It's every kid's fantasy realized on the big screen, and Ben Stiller is the perfect straight man, able to play into the wacky storm of characters coming to life around him. Owen Wilson is a lovable, teeny, tiny cowboy, and the late, great Robin Williams plays a fantastic Teddy Roosevelt. And yeah, the movie is also about a father becoming a better dad to his son, as well as a more confident, adventurous man, but that's really just a convenient tent pole to drape with fun, slapstick chase scenes, classic physical comedy gags, and cutesy history references.

Critics didn't love this movie, but it was never meant to win Oscars. This film is fun for the whole family, something to entertain everyone, and there's enough references and great performances to keep everyone engaged throughout the wild ride that is Night at the Museum. The film was wildly successful at the box office, which was plenty of incentive for studio execs to green light a sequel and then a third movie. Though the other films didn't make quite the same splash, the first Night at the Museum is still one of Ben Stiller's most beloved and imaginative movies.

Worst: Duplex was too old-fashioned for its own good

Anyone who knows anything knows about New York knows that an apartment is a sacred thing. New Yorkers love to talk real estate, and for a while in the '90s and early 2000s, there was a weird amount of movies about houses and property. Duplex is one of those movies, and it follows a couple moving into their dream home, only to find that their elderly neighbor upstairs is a living nightmare. It's a wacky comedy directed and co-written by Danny DeVito, and it stars Ben Stiller and Drew Barrymore as the aforementioned couple. But as is so often the case, talented people coming together to create doesn't always mean a recipe for success.

As the old lady upstairs begins to annoy the couple more and more, the two move towards thinking they should end her lease ... by ending her life. Any movie that's going for laughs by having the two main characters try to murder an old woman definitely qualifies as a dark comedy, but to many viewers, Duplex felt totally vacant. It was released in 2003 but felt like a holdover from an earlier time period when big, wacky gags were more acceptable, and cartoonish explosions, crashes, and mishaps were commonplace in almost every comedy.

Best: Meet the Parents is a true Ben Stiller classic

A classic comedy from 2000, Meet the Parents tells the story of one of the most harrowing, fear-inducing, white-knuckle experiences a human can have — meeting your significant other's family for the first time. 

Ben Stiller plays Greg Focker, on a trip to meet his in-laws-to-be, but what he doesn't know is that his future father-in-law, played by Robert De Niro, is an ex-CIA operative. The two instantly take a dislike to each other, and we as the audience watch Ben Stiller struggle through hilariously awkward situations. It's certainly a movie from a different time, laced with sexism and some tropes that haven't exactly aged well, but at its heart, the movie is a funny love story about the ties of family and the struggles of forging a new one. And while Ben Stiller is always excellent, many of his movies are either loved by fans and panned by critics or vice versa. However, Meet the Parents is an undeniable win because it was beloved by everyone, and its box office success spawned two sequels and inspired a few TV shows with a similar premise.

Yet again, Owen Wilson appears alongside Ben Stiller as a nemesis to great effect. That, plus the all-star cast and hilarious writing, makes this one of Ben Stiller's best.

Worst: Zoolander 2 can't compare to the original

Zoolander 2 has a lot of problems. The first being that producers totally flubbed the name, which clearly should've been Two-lander. But that's just the tip of the iceberg. Zoolander 2 came out ten years after the original, and even the signature Wilson/Stiller magic wasn't enough to relight that spark.

Once again, Derek Zoolander and Hansel must team up and return to the world of fashion to unravel a mystery and fight an enemy that threatens world peace. And once again, the movie is filled with celebrity cameos from some of the funniest and most talented actors in Hollywood. But unlike the first movie, this film wasn't liked by critics or fans.

Like so many failed sequels, Zoolander 2 plays with the same jokes and tropes as the original. Instead of trying to tell a new story, it just heats up the old one. And just like leftovers in the real world, it's not very good ten years later. Aside from the borderline offensive and definitely tone deaf portrayal of a non-binary model named All, played by Benedict Cumberbatch, the movie doesn't really bring anything new to the table.

Ultimately, the story goes way out of it's way to reference things from the original movie, and despite the amazing cast — including Penelope Cruz, Will Ferrell, and Kristen Wiig — seeing the same jokes played out ten years later by the same actors just doesn't feel right at all.

Best: The Royal Tenenbaums is a heartbreaking comedy

That rare mix of a movie that both critics and fans adore, The Royal Tenenbaums might just be the best movie on this list. This Wes Anderson film is an adult coming-of-age story and a tale about family and accepting life on its own terms. And ultimately, it's a love story.

The film features an incredible cast, including the likes of Gene Hackman, Gwyneth Paltrow, and Danny Glover. But Ben Stiller absolutely shines as Chas Tenenbaum, a neurotic and heartbroken father of two quirky, track-suit wearing sons who all return to the house he grew up in. See, Chas lost his wife, and now, he's a hilarious and tragic figure, desperately afraid that something will happen to his children, all while nursing a grudge against his long-absent father (Hackman). If this sounds like a far cry from a comedy, then you probably haven't seen the masterful way that Wes Anderson wrings the bittersweet laughs out of even the saddest situations.

A stylish movie, each frame is lovingly crafted and designed to be a mishmash of many different time periods, leaving the audience with the sense of a wholly unique but achingly familiar world. Part of the movie's success is due to its co-writer, none other than Owen Wilson, who also appears in the film. That's right, Owen Wilson and Ben Stiller are yet again acting alongside each other to give audiences and critics alike a movie to love and cherish.

Worst: We're definitely not envious of Envy

Released in 2004, Envy takes the cake for the worst-rated movie on this list, with a measly 8% over on Rotten Tomatoes. In fact, it's the perfect example of a film with an all-star cast and a decent premise that just didn't take off. Ben Stiller is once again a hapless, slightly uptight everyman named Tim Dingman whose life isn't exactly panning out. That's because his old friend, Nick Vanderpark (comedy god Jack Black), invents a spray that makes dog poo disappear, and as a result, he becomes wildly rich and successful.

As you've probably guessed from the title, Dingman becomes filled with, yep, envy, and their friendship soon turns into a rivalry. Granted, you could probably make something pretty funny out of that premise. And in addition to Stiller and Black, you've got Rachel Weisz and Amy Poehler playing their wives, respectively. You'd be hard-pressed to find a cast with more talent or higher comedy creds, and that just goes to show that good actors can't save a bad script. The jokes don't land, and even casual viewers were turned off, giving the film a Rotten Tomatoes audience score of 27%. In other words, Envy is probably the worst movie on this list ... and of Ben Stiller's career. After all, it's the film that led critic Richard Roeper to say, "One of the worst comedies I have ever seen."


Best: There's Something About Mary is both gross and great

Written and directed by the Farrelly brothers, the pop culture heroes behind Dumb and Dumber and Kingpin, There's Something About Mary was a defining film for the 1990s. It set the era's comedic tone with its raunchy jokes, wacky antics, and big heart. Plus, it's probably the textbook example of the Farrelly brothers' signature style.

Ben Stiller plays Ted Stroehmann, a hapless guy who's been in love with the same girl since high school. He lost track of her as the years went by, and truly wacky, very painful circumstances kept them apart, but he eventually hires a sleazy private investigator to track her down. But when the P.I., played by Matt Dillon, ends up falling in love with her, a love triangle and hilarity ensues. 

As the titular Mary, Cameron Diaz gives off classic '90s smoking hot girl-next-door vibes and showcases her genuine acting talent to boot. This film is beloved by adults and teens alike for its particular brand of comedy. It definitely earns its R rating with some truly gross-out humor and its numerous, painful, genital based gags. Some would say the movie is sophomoric, and some would say that's just perfect.