Can You Match The Ben Stiller Picture To The Correct Movie?


Ben Stiller has had a very long and varied career in Hollywood, and shows no sign of slowing down. Over the years he has starred in, written, directed or produced more than 50 films, and you have to go all the way back to 1987 to find his screen debut.

Naturally, he is most associated with making audiences laugh, and throughout his career he has proven he is adept at doing that in a variety of ways! But he has also starred in some top notch dramatic roles in his time, and has had a hand in writing a host of his own movies; he is clearly a man who likes having a certain amount of creative control over his projects.

Most actors would be happy to have a franchise they are involved in at some point in their career; it gives them a guaranteed audience pleaser that they know will make money, which in turn gives them more leverage in making smaller, more personal projects. But Stiller has not one, not two, but three legitimate franchises with three entries in the series!

This quiz will span the length and breadth of Stiller's career, covering several of his early indie roles, all the way through his big-budget franchise films and his directorial efforts.

How well do you know Ben Stiller? Let's find out!

Question 1

This 2000 franchise-starter solidified Stiller as a comedy star

Way back in the year 2000, Stiller teamed up with cinematic titan Robert De Niro for this modern comedy classic, which became a massive hit worldwide. It was one of the highest grossing films of the year, and was also very well-reviewed, with critics loving the comic chemistry between Stiller's character, so nervous and eager to please, and De Niro's character, so stoic and intimidating. The movie spawned two sequels, both of which were huge successes. The movie co-starred Teri Polo and Blythe Danner, and in a small but eye-catching role, Owen Wilson!

Question 2

Stiller's performance as the maniacal White Goodman in this 2004 film is hysterical

Over his career, Stiller has played a number of neurotic, nervous men who are the butt of the joke. However, he also has a talent for being completely, ludicrously over-the-top whenever he plays certain characters, and we love him for that. One of his best caricatures came in this gut-busting 2004 movie, in which he played White Goodman, the maniacal head of Globo Gym. Bizarrely, Stiller was nominated for a Golden Raspberry Award for Worst Actor for this performance, which is just...wrong!

Question 3

A beloved 70's TV show got this big screen version in 2003

Ben Stiller and Owen Wilson were, especially in the early to mid-2000's, almost inseparable on-screen. A great comedic double act, they played so well together due to Stiller's characters' uptight neuroses juxtaposing with Wilson's laidback nature. This 2003 effort, which was directed by Todd Phillips (The Hangover, Old School) and co-starred Vince Vaughn, Will Ferrell and Snoop Dogg, was a big screen version of a beloved 1970's cop show. The movie switched the personalities of the titular cops in order to better suit the actors, which rubbed some fans up the wrong way.

Question 4

Stiller co-starred with Naomi Watts and Adam Driver here

This 2014 indie comedy drama saw Stiller play a New York City documentary filmmaker who, along with his wife (Naomi Watts), begins hanging around with a much younger couple (Adam Driver and Amanda Seyfried). The film was written and directed by Noah Baumbach (The Squid And The Whale, Frances Ha) who had previously worked with Stiller on the comedy drama Greenberg This film outgrossed all of Baumbach's previous efforts, no doubt thanks to the starry cast, and it was well-received by critics.

Question 5

Stiller directed and starred in this big-budget action comedy

This 2008 action-comedy was one of Stiller's rare directorial efforts, and for our money, it's one of his very best films. As well as showing a genuine talent for action scenes and an ability to direct on a very grand scale, Stiller also starred in and co-wrote the film. Stiller plays the preposterously named Tugg Speedman, a macho action star who is thrown into a 'real' war situation while he and his castmates think they are filming a movie. Robert Downey Jr has a movie-stealing supporting role as Kirk Lazarus, a white method actor who is playing a black character, complete with racially insensitive accent and a bizarre commitment to staying in-character at all times!

Question 6

This sequel is part of Stiller's most lucrative franchise

We've already spotlighted one of Stiller's franchises in this quiz, and here's another! This is the third entry in a highly lucrative series that saw Stiller turn his attention to big-budget, CGI-heavy comedy for kids. The first movie was released in 2006, followed by the first sequel in 2009. Then, a full five years after, this third entry followed in 2013 and saw Stiller's security guard Larry Daley travel to London to return the Tablet of Ahkmenrah, the Ancient Egyptian artifact that causes museum artifacts to come to life.

Question 7

Stiller headed up a starry cast in this 2011 comedy

When the idea for this film was first pitched in 2005 by Eddie Murphy to producer Brian Grazer and eventual-director Brett Ratner, he had planned for it to star a team of black comedians who would be attempting to infiltrate a building owned by Donald Trump! We're not sure if that plot would gain any traction these days, given the current political climate. Ahem. Anyway, Stiller starred in this ensemble comedy opposite Murphy (in a true, if short-lived, return to form) and other stars such as Casey Affleck, Michael Pena and Matthew Broderick. It was pretty decent, though nothing special, and its box office performance reflected this!

Question 8

Stiller has a scene-stealing cameo in this mid-90's Adam Sandler movie

"You can trouble me for a warm glass of SHUT THE HELL UP!" Stiller has an uncredited cameo in this 1996 Adam Sandler comedy, and it's a doozy. Likely filmed as a favour to Sandler (or maybe it was simply something fun to film for a day or two), Stiller plays a sadistic orderly at Sandler's grandmother's nursing home. And when this nice, sweet old lady asks him if she could trouble him for a glass of warm milk, as it helps her sleep, he responds with the above nastiness. What a villain.

Question 9

This big-budget sci-fi comedy was torn apart by critics

This movie was one of those anomalies in Hollywood in which a large group of extremely talented comedians got together...and made a complete stinker. Oops. The movie starred Stiller, Vince Vaughn and Jonah Hill, all of whom have been genuinely hilarious in other films. It co-starred Richard Ayoade (The IT Crowd), an off-kilter comedian beloved in his British homeland. It was even co-written by Seth Rogen and Evan Goldberg, who wrote the brilliant Superbad and Pineapple Express. And yet this was painfully, inexplicably unfunny. It even bombed at the box-office too. Oh well.

Question 10

This 1999 superhero comedy has become a cult classic over the years

We can't help but think that if this 1999 superhero comedy had been released 10 or even 15 years later, during the current comic book movie boom, that it would've found a much larger audience. As it was, the film was a disaster that made less than half its budget back at the US box-office, which was a crying shame as it's actually a pretty excellent piece of superhero satire. To give you a taste of the inspired silliness, Stiller stars as Mr Furious, a 'superhero' who assumes he gains super-strength when he gets angry. But he doesn't!

Question 11

Stiller voices a cowardly lion in this hugely successful 2005 computer-animated hit

Stiller's third major franchise is this computer animated comedy series in which he plays a cowardly lion who is one of four pampered Central Park Zoo animals who are accidentally shipped to Africa and must team together to find their way back to New York. This original 2005 film spawned two sequels and a movie spin-off (and animated TV series) focussing on the scene-stealing penguins. The movie co-starred Chris Rock as a streetwise Zebra, David Schwimmer as a hypochondriac Giraffe and Jada Pinkett-Smith as a swet Hippo.

Question 12

Stiller and Ed Norton co-star with Jenna Elfman in this 2000 romantic comedy

Stiller and Edward Norton co-starred in this 2000 romantic comedy, which Norton also directed. Norton played a drunken and downtrodden Catholic Priest, while Stiller played his best friend, himself the youngest Rabbi at his Synagogue. They are both planning on opening a joint community center to unite their religions. However, the two men end up fighting over the affections of the same woman (Jenna Elfman), who had been in their lives when they were children and comes back into the scene as a vibrant, attractive adult.

Question 13

Stiller is part of a massive ensemble in this quirky 2001 Wes Anderson movie

Wes Anderson is a true cinematic auteur; a director whose movie all have an unmistakably 'Wes Anderson' vibe and style to them. They are often quirky dramas, with offbeat humour running through them, as well as a cavalcade of famous faces lining up to star in them. This one alone stars Stiller, Gene Hackman, Anjelica Huston, Bill Murray, Gwyneth Paltrow and Owen Wilson (who also co-wrote the film). The movie was a critical darling, and Gene Hackman was nominated for a Golden Globe for his performance. The screenplay was also nominated for an Academy Award.

Question 14

Another brilliant cameo from Stiller in this Jack Black effort

Jack Black is, like Stiller, a multi-talented guy. He's an actor, a writer and a producer, but he goes even further by being a singer and a musician as well! In 2006, a movie was released which detailed the (heavily fictionalized) early 1990's origins of Black's real life band, which he formed in 1994 with Kyle Gass. The movie was a box-office dud, unfortunately, but it did feature cameos from some Hollywood elite: Tim Robbins, John C. Reilly, Amy Adams and Stiller all appear at various points!

Question 15

'Maybe there's more to life than being really, really, really ridiculously good looking?'

In 2001, Stiller's definitive character (in our humble opinion) debuted on the big screen. Based on two short films co-written by Stiller and made in 1996 and 1997 for the VH1 Fashion Awards TV Specials, this film told the story of a dim-witted male model becoming the pawn of evil fashion moguls plotting to assassinate the Prime Minister of Malaysia. Which is just as ridiculous, and hilarious, as it sounds. The movie co-starred Owen Wilson, Will Ferrell and Christine Taylor, and became a cult classic over the years. This led to a much-delayed sequel in 2016...which sucked. But we'll always have the original movie!

Question 16

This disappointing Farrelly Brothers comedy was released in 2007

Undoubtedly one of the more forgettable movies in Stiller's career, this Farrelly Brothers comedy was released in 2007 and co-starred Malin Akerman, Michelle Monaghan and Danny McBride. It was a remake of a 1972 film, but originally was given a different title: The Seven Day Itch. Unfortunately, the filmmakers lost a lawsuit over the title and after they were unable to agree on a new title, had to settle for the original title of the '72 film. The idea of a man marrying his ideal woman, then discovering on their honeymoon how mismatched they are, certainly has a lot of potential for laughs. Sadly, they turned out to be few and far between here!

Question 17

This franchise sequel introduced Dustin Hoffman and Barbra Streisand to the mix

Four years after the original movie, this sequel was released in 2004. It became an even bigger hit than the first one, and in fact, still stands as Robert De Niro's highest grossing movie ever! Stiller and De Niro's chemistry was as strong as ever, but this time they were joined by Dustin Hoffman and Barbra Streisand as Stiller's parents, and they brought a great many laughs to the table as well. But the movie might very well be best remembered for the image of De Niro, one of cinema's most intimidating presences, wearing a homemade breastfeeding apparatus for men, which he dubbed the 'Mannary Gland'. Priceless!

Question 18

Stiller shot to fame in this classic 1998 gross-out comedy

Prior to this 1998 romantic comedy, directed by the Farrelly Brothers, Stiller was mostly known for his MTV comedy sketch show The Ben Stiller Show, as well as appearances in movies like Flirting With Disaster and Reality Bites. But he shot to fame as a leading comic actor after this movie, which also starred Cameron Diaz, Matt Dillon and Lee Evans. The movie had a few iconic scenes, one of which involved Diaz' character mistaking a...substance for hair gel, and another which involved Stiller's character getting his boy parts caught in his zipper! Ouch!

Question 19

Stiller played Spanish reporter Arturo Mendes in this bizarre cameo

Another scene-stealing cameo here for Stiller, as a Spanish reporter with a preposterous moustache! This classic 2004 comedy was Will Ferrell's coming-out party as a leading man, and also helped familiarize the world with the comic stylings of Paul Rudd and Steve Carell (who would go on to star together in The 40-Year Old Virgin the next year). Christina Applegate and David Koechner also starred, and the movie wound up becoming responsible for providing people with amazing quotes for years to come. Well, quotes that started out amazing, but maybe have crossed over into annoying territory after such repetition!

Question 20

This 2004 romcom is surprisingly funny

Stiller has starred in quite a few romantic comedies, but we reckon this one is up there in the upper tier of those efforts. Namely, because it's actually funny, and also actually sweet and endearing. So that's a win! Stiller starred as Reuben Feffer, a neurotic risk-assessor, who becomes romantically involved with Jennifer Aniston's character, a freewheeling and carefree woman who is the exact opposite of himself. It's all quite predictable, but the cast plays it well, and a lot of laughs come from supporting players like Phillip Seymour Hoffman (in a rare comedy role) and Hank Azaria as a musclebound Frenchman obsessed with 'scuba'.

Question 21

This surreal 2013 remake stuttered at the box office

All in all, Stiller has directed seven films in his career, which is likely more than many people would think. This 2013 remake was one of his directorial efforts, and it was a new version of a 1939 short story by James Thurber (which had previously also been adapted to film in 1947). The movie co-starred Kristen Wiig, Shirley MacLaine, Sean Penn and Adam Scott, and told the story of a bored negative assets manager working at Life Magazine who has vivid daydreams of himself on grand adventures.

Question 22

Stiller directed this controversial 1996 black comedy

Eagle eyed quiz takers may recognize that, yes, that is NOT Ben Stiller in the picture! It's actually Jim Carrey, who starred in this 1996 black comedy that was directed by Stiller. It had a decidedly mixed reception upon its release, due mainly to the darker tone than Carrey's usual comedies at that time. It has since gone on to gain a cult following on VHS and DVD, and perhaps audiences just weren't ready in 1996 for Carrey to subvert his rubber-faced image so much. Stiller cameos in the film.

Question 23

This 1998 mystery film paired Stiller with Bill Pullman

Jake Kasdan is a director with a few hits under his belt: Sex Tape and Bad Teacher to name a few. He is also the director of the current Jumanji sequel starring Dwayne Johnson, Kevin Hart and Jack Black. But back in 1998, he made his feature film debut with this mystery drama starring Bill Pullman as 'the World's Most Private Detective' and Stiller as his assistant. The plot of the film is loosely based on the Sherlock Holmes story 'A Scandal In Bohemia', but the makers updated it to modern day and shot it through with some off-kilter humour.

Question 24

This 2004 flop is a black mark on both Stiller and Jack Black's CV's

This 2004 disaster was actually filmed in 2002, but wound up being left on the studio shelf due to poor audience reaction to test screenings. In fact, it was in danger of going straight to home video until Jack Black's star rose in 2003, which convinced the studio to finally give it a theatrical release. In hindsight, they probably shouldn't have! Stiller and Black played best friends and neighbours Tim and Nick, and when Nick invents a spray that instantly removes dog poo (seriously), Tim's anger toward his friend grows exponentially as Nick gets richer and richer.

Question 25

This 1987 Spielberg war epic also starred a 12-year-old Christian Bale

Steven Spielberg directed this 1987 coming-of-age war film, which was based on a semi-autobiographical novel by J.G. Ballard (Crash, High-Rise). John Malkovich and Miranda Richardson starred alongside a 12-year-old newcomer, who was chosen after more than 4000 child actors auditioned: Christian Bale! Yep, Batman has been on our screens for much longer than you might think! Stiller has a small role in the film, though a mistake he made on-set made a big impression. He screwed up his line and audibly said 'Maybe we should cut?', which ruined a six-minute shot, and raised the ire of Spielberg who responded with 'No! No, you never cut!'. Apparently they've laughed about it in the years since, but Stiller said he was mortified.

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