Early Roles
What TV sitcom gave Leo his first major break as a recurring character?
Growing Pains
In Inception, what object does Leo’s character use to test reality?
What is a spinning top?
Who played Rose opposite Leo in Titanic?
Who is Kate Winslet?
For which film did Leo win his first Oscar?
What is The Revenant?
In Catch Me If You Can, Leo plays this real-life con artist.
Who is Frank Abagnale Jr.?
In which 1993 film did Leo play a mentally challenged boy opposite Johnny Depp?
What is What's Eating Gilbert Grape?
Who directed Shutter Island and The Departed, both starring Leo?
Who is Martin Scorsese?
Who played Juliet opposite of Leo in Romeo and Juliet?
Who is Claire Danes?
How many times has Leo been nominated for an Academy Award (as of 2024)?
What is 7
Leo portrayed this eccentric billionaire and aviation pioneer in The Aviator.
Who is Howard Hughes?
What was Leo’s character’s name in Titanic?
Who is Jack Dawson?
What is the name of the plantation owned by Leonardo DiCaprio’s character, Calvin Candie, in the Western thriller Django Unchained?
What is Candyland?
In The Great Gatsby, who is Gatsby hopelessly in love with?
Who is Daisy Buchanan?
For which Quentin Tarantino film was Leonardo DiCaprio nominated for an Academy Award for Best Actor?
What is Once Upon a Time in Hollywood
In The Wolf of Wall Street, Leo plays this controversial stockbroker.
Who is Jordan Belfort?
Which 1995 western featured Leo as “The Kid”?
What is The Quick and the Dead?
In The Departed, what is Leo’s undercover role?
What is a cop infiltrating the mob?
Who portrayed Sharon Tate in Once Upon a Time in Hollywood?
What year did Leo finally win his first Oscar?
What is 2016?
What 2011 film stars Leo as the longtime FBI director?
What is J. Edgar?
What was Leo’s first Oscar nomination for?
What is What's Eating Gilbert Grape?
Who directed the 2010 film that Leo starred in which features dream layers and subconscious espionage?
Who is Christopher Nolan?
In addition to Titanic, which 2008 film featured Leonardo DiCaprio and Kate Winslet together on screen?
What is Revolutionary Road?
Which film earned Leonardo DiCaprio a Best Actor nomination the same year Jamie Foxx won for portraying Ray Charles?
What is The Aviator?
In which film did Leonardo DiCaprio portray a fictional actor set against the backdrop of the real-life Manson Family murders and the death of Sharon Tate?
What is Once Upon a Time in Hollywood?