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We Love Leo: 12 Books Leonardo DiCaprio Brought to the Silver Screen

Tolani Osan joined Simon & Schuster’s Associate’s Program in 2015 where she spent her first rotation in S&S publicity. She recently earned a Master’s in Publishing & Writing from Emerson College. A daughter of Nigerian immigrants, Tolani enjoys literary fiction about the tensions between cultures and classes. Her favorite book is Khaled Hosseini’s “A Thousand Splendid Suns,” which she’s made a pact with herself to revisit every three years. She also founded and runs women’s interest blog, MyDresscapades.com, and writes on topics such as fashion, food, perpetual “singledom”, and feminism. You can enjoy her musings about pop culture, fashion, and literature on twitter @dresscapades  

I think we can all agree that Leonardo DiCaprio’s 2016 Oscar for Best Actor was hard-won. But even before he brought Michael Punke’s novel, THE REVENANT, to life, DiCaprio had a long history of delivering phenomenal performances in book-to-film adaptations. Though he’s noticeably absent from this year’s Oscar ballot, we’re still swooning over Leo. From his teen-heartthrob days to his most powerful performances, here’s a look a Leonardo DiCaprio’s career in page-to-screen adaptations.


This Boy's Life
by Tobias Wolff
After his “Growing Pains” days, Leo’s first major feature film role was as a young Toby Wolff in the 1993 film “This Boy’s Life.” The film is based on Wolff’s coming-of-age memoir about his fight for identity and self-respect against the unrelenting hostility of a new stepfather.
This Boy's Life
Tobias Wolff

A beautifully written memoir that at times is hard to read because the story is so intense. A teen-aged Wolff hops from state to state with his mother to escape her violent boyfriend yet when she finally remarries it's to a brutal abusive man. Wolff finds himself in a bitter battle of wills with this bully of a stepfather that is riveting.

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We Love Leo: 12 Books Leonardo DiCaprio Brought to the Silver Screen

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What's Eating Gilbert Grape
by Peter Hedges

Leo’s portrayal of Arnie Grape in the 1993 film “What’s Eating Gilbert Grape” is arguably one of the most memorable of his career. It also marked the first of his many Oscar nods (and losses). The Peter Hedges novel on which the film is based follows Gilbert Grape (played by Johnny Depp): a 24-year-old grocery clerk stuck in a microscopic Iowa town where he looks after his morbidly obese mother and mentally disabled brother, Arnie.

What's Eating Gilbert Grape
Peter Hedges

Leo’s portrayal of Arnie Grape in the 1993 film “What’s Eating Gilbert Grape” is arguably one of the most memorable of his career. It also marked the first of his many Oscar nods (and losses). The Peter Hedges novel on which the film is based follows Gilbert Grape (played by Johnny Depp): a 24-year-old grocery clerk stuck in a microscopic Iowa town where he looks after his morbidly obese mother and mentally disabled brother, Arnie.

MENTIONED IN:

We Love Leo: 12 Books Leonardo DiCaprio Brought to the Silver Screen

By Tolani Osan | February 24, 2017

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Basketball Diaries
by Jim Carroll
Jim Carroll, portrayed by DiCaprio in the 1995 film, grew up to become a renowned poet and punk rocker. But in the 60s, he was a rebellious teenager making a name for himself on the unforgiving streets of New York City. In his memoir, THE BASKETBALL DIARIES, Carroll shares diary entries of his restless youth and the result is an urban classic coming-of-age story about sex, drugs, and basketball.
Basketball Diaries
Jim Carroll

The story of a 60's New York Catholic school boy who sniffs glue at thirteen and winds up a strung out street hustler working for his next fix at age 16. Lyrical, wry, funny and so intensely raw in its depiction of his descent and his struggle to maintain, this memoir is a classic. Leaves the Leo DiCaprio film in the dust.

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Romeo and Juliet
by William Shakespeare
In the thick of his heartthrob era, Leo starred in the 1996 modern-day adaptation of the most famous romantic tragedy of all time: ROMEO AND JULIET. The Baz Luhrmann–directed movie is a cult classic for those who watched it as teenagers and for 90s enthusiasts. DiCaprio plays Romeo opposite Claire Danes’s Juliet.
Romeo and Juliet
William Shakespeare

“A plague o’ both your houses!/They have made worms’ meat of me: I have it,/And soundly too. Your houses!” —Mercutio

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The Man in the Iron Mask
by Alexandre Dumas

DiCaprio acted as both King Louis XIV and his mysterious twin brother, Philippe, in the 1998 adaptation of Alexandre Dumas’s final Musketeers book. In THE MAN IN THE IRON MASK, the Musketeers have gone their separate ways, but D’Artagnan remains in the service of the corrupt king. Soon, the Three Musketeers find themselves caught between conflicting loyalties when King Louis XIV and Philippe’s destinies begin to converge.

The Man in the Iron Mask
Alexandre Dumas

DiCaprio acted as both King Louis XIV and his mysterious twin brother, Philippe, in the 1998 adaptation of Alexandre Dumas’s final Musketeers book. In THE MAN IN THE IRON MASK, the Musketeers have gone their separate ways, but D’Artagnan remains in the service of the corrupt king. Soon, the Three Musketeers find themselves caught between conflicting loyalties when King Louis XIV and Philippe’s destinies begin to converge.

MENTIONED IN:

We Love Leo: 12 Books Leonardo DiCaprio Brought to the Silver Screen

By Tolani Osan | February 24, 2017

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The Beach
by Alex Garland

In his suspenseful debut novel, THE BEACH, Alex Garland illuminates a generation in their twenties burdened with the legacy of the preceding generation and saturated by popular culture. Leonardo DiCaprio was in his twenties when he played a young man who sets off to explore an idyllic beach forbidden to tourists in Bangkok. But it soon becomes clear that The Beach has troubling, even deadly, undercurrents.

The Beach
Alex Garland

In his suspenseful debut novel, THE BEACH, Alex Garland illuminates a generation in their twenties burdened with the legacy of the preceding generation and saturated by popular culture. Leonardo DiCaprio was in his twenties when he played a young man who sets off to explore an idyllic beach forbidden to tourists in Bangkok. But it soon becomes clear that The Beach has troubling, even deadly, undercurrents.

MENTIONED IN:

We Love Leo: 12 Books Leonardo DiCaprio Brought to the Silver Screen

By Tolani Osan | February 24, 2017

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Catch Me If You Can
by Frank W. Abagnale
DiCaprio teams up with Hollywood greats Steven Spielberg and Tom Hanks in this true cat-and-mouse story, “Catch Me If You Can.” The Oscar-nominated film is based on a memoir by Frank W. Abagnale (aka Frank Williams, Robert Conrad, Frank Adams, and Robert Monjo)—the world’s most sought-after con man.
Catch Me If You Can
Frank W. Abagnale

Frank W. Abagnale, alias Frank Williams, Robert Conrad, Frank Adams, and Robert Monjo, was one of the most daring con men, forgers, imposters, and escape artists in history. In his brief but notorious criminal career, Abagnale donned a pilot's uniform and copiloted a Pan Am jet, masqueraded as the supervising resident of a hospital, practiced law without a license, passed himself off as a college sociology professor, and cashed over $2.5 million in forged checks, all before he was twenty-one. The basis for the great Leo DiCaprio film, hopefully he's not flying your plane.

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Body of Lies
by David Ignatius

In David Ignatius’s spy thriller, CIA soldier Roger Ferris (played by DiCaprio in the 2008 adaptation) must penetrate the network of a master terrorist known only as "Suleiman." His scheme binds friend and foe in a web of extraordinary complexity. When it begins to unravel, Ferris’s only hope is the head of Jordan's intelligence service. But can he trust him?

Body of Lies
David Ignatius

In David Ignatius’s spy thriller, CIA soldier Roger Ferris (played by DiCaprio in the 2008 adaptation) must penetrate the network of a master terrorist known only as "Suleiman." His scheme binds friend and foe in a web of extraordinary complexity. When it begins to unravel, Ferris’s only hope is the head of Jordan's intelligence service. But can he trust him?

MENTIONED IN:

We Love Leo: 12 Books Leonardo DiCaprio Brought to the Silver Screen

By Tolani Osan | February 24, 2017

Close

Revolutionary Road
by Richard Yates
Although Leo didn’t score any Oscar nods for his heartrending performance as the hopeless suburban-dweller Frank Wheeler, the adaptation of the Richard Yates novel was a formidable contender at the 2009 Academy Awards. REVOLUTIONARY ROAD tells the story of a young couple raising their two children in a Connecticut suburb during the mid-1950s while struggling to come to terms with their personal problems.
Revolutionary Road
Richard Yates

An evocative portrayal of the opulent desolation of the American suburbs, Revolutionary Road is perhaps literature’s most penetrating portrait of the Mad Men era. The story of a couple who have lived on the assumption that greatness is only just around the corner, Richard Yates demonstrates with heartbreaking compassion and remorseless clarity how Frank and April betray not only each other, but their best selves.

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Shutter Island
by Dennis Lehane
Martin Scorsese directed DiCaprio in this 2010 psychological thriller based on Dennis Lehane’s mind-bending novel. Like its film counterpart, SHUTTER ISLAND delivers a twist to put all plot twists to shame. DiCaprio plays U.S. Marshal Teddy Daniels, who visits a hospital for the criminally insane on the isolated and eerie Shutter Island.
Shutter Island
Dennis Lehane

Multiple murderess Rachel Solando is loose somewhere on Shutter Island, home of Ashecliffe Hospital for the Criminally Insane, and U.S. Marhsal Teddy Daniels and Chuck Aule are on the case. As a killer hurricane bears down on the island, hints of radical experimentation and covert government machinations add darker, more sinister shades to an already bizarre case. Just as deliciously un-put-down-able and full of twists and turns as a Gillian Flynn favorite.

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By Tolani Osan | February 24, 2017

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The Great Gatsby
by F. Scott Fitzgerald
Though DiCaprio was not the first to portray the fabulously wealthy Jay Gatsby on the silver screen, this adaptation directed by Baz Luhrmann probably came closest to displaying the opulence of a Gatsby-thrown party. F. Scott Fitzgerald’s Jazz Age classic is an exquisitely crafted tale of America in the 1920s.
The Great Gatsby
F. Scott Fitzgerald

Some consider it “the great American novel.” The story of the fabulously wealthy Jay Gatsby and his powerful love for the beautiful Daisy Buchanan is an exquisitely crafted tale that has been essential reading since it was published.

Read the full review here.

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The Wolf of Wall Street
by Jordan Belfort

Leo teamed up with Martin Scorsese again to bring to life the story of Wall Street kingpin Jordan Belfort and illuminate the corruption on Wall Street in the 1990s. By day Belfort made thousands of dollars a minute at the notorious investment firm Stratton Oakmont. By night he spent it as fast as he could, on drugs, sex, and international globe-trotting. In this astounding and hilarious tell-all autobiography, Belfort narrates a story of greed, power, and excess that no one could invent.

The Wolf of Wall Street
Jordan Belfort

Leo teamed up with Martin Scorsese again to bring to life the story of Wall Street kingpin Jordan Belfort and illuminate the corruption on Wall Street in the 1990s. By day Belfort made thousands of dollars a minute at the notorious investment firm Stratton Oakmont. By night he spent it as fast as he could, on drugs, sex, and international globe-trotting. In this astounding and hilarious tell-all autobiography, Belfort narrates a story of greed, power, and excess that no one could invent.

MENTIONED IN:

We Love Leo: 12 Books Leonardo DiCaprio Brought to the Silver Screen

By Tolani Osan | February 24, 2017

Close

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