Who Can Name All Of These Leonardo DiCaprio Movies?

Today's quiz will determine who the true fans of Leonardo DiCaprio are! We're looking for the folks who know all his movies, not just the ones that were commercially successful like Titanic and The Wolf of Wall Street. We want the people who seen his earlier movies too and who know him from his more obscure roles. These are the fans who will be able to score 100% on this one.

DiCaprio began his career in entertainment as a child, working first in commercials before moving up to small TV roles. He eventually landed a small role in a film and gradually began to pick up more and more roles as people began to notice his talent. His breakout role came in 1996 when he played the role of Romeo in Baz Luhrmann's Romeo + Juliet. Just one year later he starred in James Cameron's Titanic, a film which went on to become the highest grossing film of all time at that point. Since then he's starred in dozens of successful films including titles such as The Revenant, Shutter Island, Inception, and The Departed.

To ace this quiz simply match the picture with the correct Leonardo DiCaprio movie. Any true fan should have no trouble getting them all right!

Question 1

In which 2000 movie did DiCaprio play a young traveller?

In this film, a young DiCaprio played the role of a traveler looking for adventure away from the regular tourist traps. He learns about an island where wanderers like himself are living in a small freewill society and decides to try and join them. This movie didn't fare so well at the box office but even if the storyline wasn't that strong it's still worth a watch for the beautiful location and to see DiCaprio losing his mind. Anyone remember the name of this movie?

Question 2

Who can match this picture to the right movie?

In this 2006 Martin Scorsese crime drama DiCaprio starred alongside Matt Damon and Jack Nicholson as an undercover cop trying to infiltrate a notorious Boston gang. But little does he know that he's not the only rat around because Matt Damon's character is also playing both sides. It's an edge of your seat game of cat and mouse all the way as each side tries to discover who is selling them out. Who can remember the name of this gripping movie?

Question 3

In which movie did he play the role of Frank Wheeler?

No one wants to end up working long hours at a job they hate and feeling unfulfilled but sometimes it happens so gradually that we don't even notice. In this movie, set in the 1950's, DiCaprio plays the role of a husband who finds himself in this position and decides to take drastic steps to have a more fulfilling life with this wife (played by Kate Winslet, who also starred with him in Titanic). Who knows the name of this 2008 romantic drama?

Question 4

In which Quentin Tarantino flick did he play Calvin Candie?

In this 2012 drama, Quentin Tarantino-directed flick DiCaprio plays the supporting role of a plantation owner named Calvin Candie, a shady character who enjoys making his slaves fight each other and punishing them in extreme ways. The two heroes of the story Django (played by Jamie Foxx) and Dr. Schultz (portrayed by Christopher Waltz who you'll also remember as Hans Landa from Inglorious Basterds) arrive at Candie's sprawling homestead with the hidden intention of freeing Django's long-lost wife from slavery. What was the name of this movie?

Question 5

What was the name of this 2016 documentary film?

DiCaprio uses his fame to bring attention to the causes he is passionate about and one of them is the environment. In this eye-opening 2016 documentary, he meets with all types of activists, scientists, specialists and world leaders to discuss the impending dangers associated with climate change and the possible solutions to this global problem. This movie won the award for Best Documentary at the Evening Standard British Film Awards as well as the Hollywood Documentary Award at the Hollywood Film Awards. What is it called?

Question 6

In which 1993 coming of age film did he star with Robert De Niro?

As kids, we often have very little say about where we live and who our parents decide to get into relationships with. That was the case for the lead character in this 1993 coming-of-age film, played by a young Leonardo DiCaprio. In this movie, his mother meets a man who she initially thinks is perfect for her and her son but as time goes on she realizes that he wants to control everyone around him. The young characters only hope to escape from his dreadful home life is to get a scholarship...

Question 7

In which movie did he play Hugh Glass?

Just how much can one man survive? Well before you answer that you should watch this movie again! This film told the true (yes, it's all true) story of Hugh Glass, a frontiersman betrayed by his fellow men and left to die in the wilderness after a brutal bear attack. But this was a man who a never say die attitude and it would take a lot more than a bear to stop him. DiCaprio deservedly picked up the Academy Award for Best Actor for this role.

Question 8

What was this short film by Martin Scorsese called?

Some folks say they are DiCaprio fans but they only really know him from his mainstream, big budget movies. Start asking them about his early roles, documentaries or short films (like this one) and they draw a blank. This 2015 short film was directed by Martin Scorsese (whom DiCaprio has collaborated with many times) and starred Robert De Niro and Leonardo DiCaprio as fictionalized versions of themselves competing for a role in Scorsese's next movie. Any super fans want to tell us the name of this movie?

Question 9

Which movie did Leonardo DiCaprio make his film debut in?

Leo started his career in entertainment at a young age, appearing first in commercials and working his way up to small TV roles. His film debut came in 1991 when he played a role in a horror film, which went directly to video upon release. But his breakout role followed just a few years later. This movie was his starting point and it would lead him all the way to where he is today: superstar status. What was the name of this movie?

Question 10

In which 1993 film did he star along with Johnny Depp?

In this 1993 drama film, Leonardo co-starred as the mentally handicapped brother of a character played by Johnny Depp. The director of this movie was initially relucent to hire DiCaprio as he felt he was too good-looking for the role but he was impressed by his skills and decided to cast him. The film was a critical success and people started to notice that Leo had a rare talent. His breakout movie followed just three years later. What was the name of this film?

Question 11

Which DiCaprio film was this?

Anyone who doesn't instantly recognize this film has no place calling themselves a fan of Leo in any way, shape or form. This was the movie that took him from star to superstar status, practically overnight. In this movie, he played the love interest of Kate Winslet's character abroad an ill-fated passenger cruise liner. The film, directed by James Cameron, was the highest grossing film of all time until the release of Avatar in 2010. What was the name of this movie?

Question 12

In which movie did he pose as a doctor?

In this movie, DiCaprio plays the role of a cunning young man who runs away from home and makes a life for himself by pulling off daring confidence tricks. He pretends to be an airline pilot; traveling thousands of miles for free, a lawyer, and at one stage even a doctor; in charge of a hospital emergency room. He's a master of cheque fraud but eventually, the long arm of the law (in this case Tom Hanks) catches up with him.

Question 13

In which movie did he have a South African accent?

Skilled actors are able to play all types of different characters, sometimes even changing their voices to affect different dialects and accents. Some are more difficult than others to get right and one of the harder ones is the South African Afrikaner accent. This was the accent that Leonardo DiCaprio had to perfect for his role in this gritty 2006 drama and he pulled it off perfectly. In this story, DiCaprio and Djimon Hounsou play a mercenary and a fisherman respectively who team up to try and recover a rare gem during the midst of a war-torn Sierra Leone.

Question 14

Match this picture to the right DiCaprio flick:

We have to be in the right mood to really enjoy an intense thriller like this but it's worth it for the performances. In this film, another Martin Scorsese neo-noir thriller flick Leonardo DiCaprio's character travels to a mental hospital located on an island and becomes trapped there as a storm blows in. He thinks he is there to investigate the disappearance of one of the patients but that's not the case at all. Who remembers the name of this 2010 film?

Question 15

What the name of this mind-bending movie?

In this 2010 movie, DiCaprio plays the role of Dom Cobb, a thief who is able, thanks to high-tech equipment, to enter into people's dreams and steal ideas and secrets straight from their subconscious, without them ever being aware of what happened. He gets offered the opportunity to take on a new assignment but for this one, he will need to implant an idea instead of steal one. This mind-bending thriller also starred Tom Hardy, Ellen Page, and Joesph Gordon Levitt. What was it called?

Question 16

In which movie was he Jay Gatsby?

Leo first worked with director Baz Luhrmann during the making of Romeo + Juliet in the mid-90's. In 2013 he once again took on a leading role in one of Luhrmann's films, this time as a wealthy socialite during the Roaring Twenties. The film was a hit with audiences and critics and became Luhrmann's highest grossing film to rate, raking in a smooth $353 million off a $190 million budget. It also picked up two Academy Awards: Best Production Design and Best Costume Design. Name this film for us.

Question 17

In which movie was he the director of the FBI?

Often the most compelling stories aren't the type dreamed up by writers but those that really happened. These can of personal stories are often even more outrageous than any fictional story. In this biographical movie, DiCaprio plays the role of a real-life person with such a story, a man made famous by his job as the director of the FBI. The film, which also featured Naomi Watts and Judi Dench, was released in 2011. Anyone know the name of this one?

Question 18

In which movie did he play poet Arthur Rimbaud?

This is one of Leonardo's lesser known films but a true fan should have no problem giving us the title. This film, which was released in 1995, just a year before Leonardo enjoyed his breakout role in Romeo + Juliet, tells the story of a 19th-century poet named Arthur Rimbaud and his stormy sometimes violent relationship with Paul Verlaine, also a poet. The story is historically accurate and based on letters and poems written by the two men. What was the name of this film?

Question 19

Match this character to the right movie:

This 1995 western film starred Leonardo DiCaprio as well as Sharon Stone, Gene Hackman, and Russel Crowe. In this movie, DiCaprio played the role of Fee "The Kid" Herod, the owner of a gun store. At the time Leonardo was not a big name yet and the studio was relucent to hire him but Sharon Stone, who believed in the young up and coming actor, paid his salary for the movie herself. Which Leo fans can tell us the name of this movie?

Question 20

In which movie was DiCaprio King Louis XIV?

Pulling off one character in a movie is impressive, but pulling off two very different characters in the same movie takes some mad skills. And as we know, Leo has those! In this 1998 action drama, he plays the role of both the villain and the hero. He plays the role of the tyrannical King Louis XIV and the part of a mysterious prisoner who is forced to wear a bulky type of mask in order to conceal his face. What was this movie called?

Question 21

What was the name of this period drama?

This 2002 epic period drama followed the story of a New York gang leader named William "Bill the Butcher" Cutting (played by Daniel Day-Lewis). In this movie, Leonardo DiCaprio played the role of the protagonist who comes up against Bill. Directed by the legendary Martin Scorsese this film received ten Academy Awards for it's gritty and original storyline. Unfortunately, Leo didn't win any awards for this one although Daniel Day-Lewis walked off with an Oscar for this work. What was this movie called?

Question 22

In which movie was Leo a CIA operative in Iraq?

Who doesn't love a good spy thriller right? All the intrigue, all the excitement, all the gadgets...But often the spy movies that we end up watching don't really give us an accurate portrayal of how things really are. The world of espionage is crammed full of politics, most of it internal, and that can be the trickiest obstacle to overcome. In this 2008 spy movie, DiCaprio plays the role of a CIA operative stationed in the Middle East. What was the name of this film?

Question 23

Match this picture to the correct DiCaprio movie:

There are only two ways to make money: honestly and dishonestly. Most of us prefer to make our money the hard way, through hard work because we have integrity and we couldn't sleep at night knowing that we ripped someone off. But not everyone is like that and in this hit movie, Leonardo DiCaprio played the role of a man who wanted to make it to the top, no matter what he had to do. Which fans can name this movie for us?

Question 24

Which 2001 black and white indie film did Leo try and prevent from being released?

This one is for the hardcore fans! This 2001 low budget black and white indie film directed by R.D Robb featured Leonardo DiCaprio, Tobey Maguire, and Kevin Connolly and follows a group of young friends who spend a night at a diner discussing life. DiCaprio and Maguire later tried to stop the film from being released and eventually a court ruled that it would only be released outside the USA and Canada. It is still blocked from being aired in these countries and that's why only hardcore DiCaprio fans will know the name of this obscure film. Does anyone want to guess?

Question 25

In which 90's film did he play the role of Hank Lacker?

This 1996 family drama followed the lives of two sisters, one who fled from her family after her father suffered a stroke and one who remained behind to care for him for more than two decades. After being estranged for many years the two are forced to reconnect after the one is diagnosed with cancer. In this film, Leo plays the role of one of the sisters' son's who spends time in a mental institution. Who remembers the name of this one?

Question 26

In which movie did he play Frank Abagnale?

In this hit film, Leonardo DiCaprio starred as Frank Abagnale, a young but enterprising runaway who managed to amass a small fortune posing as an airline pilot, a doctor, and a lawyer, all before his 19th birthday. Working as a confidence trickster his main crime was check fraud and this eventually got him caught by the FBI. But he was so skilled that the agency ended up using his knowledge to help them catch other forgers. What was the name of this 2002 biographical crime drama?

Question 27

Match this picture to the right movie:

In this controversial 1995 coming-of-age drama flick, Leonardo DiCaprio plays the role of an up and coming high school basketball player and budding writer with a promising future who develops a drug addiction and spirals out of control, eventually living on the streets. But after reaching his lowest point he ends up serving time and this is when he manages to turn his life around. This film was based on the life of real-life poet and memoirist Jim Carroll. What was the name of this movie?

Question 28

Which 90's film was this?

In one of the most popular re-tellings of this Shakespean tale of love and tragedy, Leonardo took the leading male role alongside Claire Danes in this 1996 MTV-inspired Baz Luhrmann film. The two meet when Leonardo's character crashes a party and instantly fall in love but soon discover that they have a problem; their families hate each other. It's one of the most well-known love stories of all times and the film that helped DiCaprio make it onto the A-list. What is the name of this movie?

Question 29

Which 1998 Woody Allen film did he star in?

This 1998 comedy-drama was directed by Woody Allen and featured a star-studded ensemble cast which included Leonardo DiCaprio, Kenneth Branagh, Judy Davis, Melanie Griffith, Winona Ryder, and Charlize Theron. The film follows the lives of a couple who both pursue careers in celebrity journalism after their divorce. The film was a commercial failure, bombing at the box office and making only $5 million dollars on a $12 million budget. Did anyone see this movie? Can you tell us the name of this one?

Question 30

In which film did Leo play the role of Howard Hughes?

In this Martin Scorsese film, DiCaprio played the role of Howard Hughes, an aviation pioneer, and film director. The film follows his life from 1927–1947 when he reached the pinnacle of both his film career and as an aviation magnate while suffering from debilitating OCD(Obsessive Complausive Disorder) and gradually becoming more and more mentally unstable. This biographical film was released in 2004 and also starred Cate Blanchett (as Katharine Hepburn) and Kate Beckinsale (as Ava Gardner). Which DiCaprio fan can name this movie for us?

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