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  1. Entertainment
  2. Movies

The Evolution of Leonardo DiCaprio

Features
By Matt Maytum published 13 July 2010

The Inception star, film by film…

When you purchase through links on our site, we may earn an affiliate commission. Here’s how it works.

The Outsiders/ The Young Lassie/ Santa Barbara (1990)

The Outsiders/ The Young Lassie/ Santa Barbara (1990)

A fifteen-year-old Leonardo DiCaprio got his first taste of public exposure with this trio of TV shows in 1990.

The Outsiders (based on the film of the same name) was exec-produced by Francis Ford Coppola , The New Lassie (pretty much what is says on the tin) saw him fleetingly portray 'Young Boy', and in a five-episode run of Santa Barbara Leo was dignified with a character name.

Does he die? The lives of these minor characters were pretty much irrelevant anyway.

Page 1 of 27
Page 1 of 27
Roseanne (1991)

Roseanne (1991)

Leo made an appearance in the long-running sitcom, which was a pretty big ratings hit and could've really got him noticed.

Sadly the little fella went uncredited in a background role as one of Darla's classmates. In the episode, Roseanne gives a talk on being a housewife at Darla's school, and you can momentarily glimpse the blonde moppet in the background.

Does he die? Who knows what has happened to Darla's enigmatic classmate? Answers on a postcard.

Page 2 of 27
Page 2 of 27
Parenthood (1990-1991)

Parenthood (1990-1991)

Another chance for DiCaprio to cut his teeth on a TV version of a well-known movie property (after Lassie and The Outsiders ) .

Leo was one of the Buckman kids, and he earned pretty good notices considering the show's limited one season run (only 12 episodes were made).

The show also benefited from the fact that it wasn't as terrible as some of the other movie-to-TV adaps doing the rounds at the time, including Ferris Bueller , Uncle Buck and Working Girl .

Does he die? No, but the show was killed after one series.

Page 3 of 27
Page 3 of 27
Critters 3 (1991)

Critters 3 (1991)

Leo made his first big screen appearance in the third in the Critters series.

While the original Critters was no Gremlins , it was still pretty decent B-movie fun, helped along by some knowing humour.

By the time the third movie came out, people were starting to lose patience with the ferocious Krites, as the pretty one-dimensional joke couldn't take the stretch to franchise length.

Does he die? He actually manages to survive the killer space hedgehogs' attack on his stepdad's tenement.

Page 4 of 27
Page 4 of 27
Growing Pains (1991-1992)

Growing Pains (1991-1992)

After Critters 3 , Leo was back for another run on the small screen, appearing as a supporting character in the seventh (and final) series of this sitcom.

He was homeless kid Luke Brower who briefly lived with shrink Jason Seaver and his family. Throughout its run, Growing Pains also acted as a stepping stone for Brad Pitt, Hilary Swank and Heather Graham.

By the time of the reunion movie in 2000, DiCaprio had moved onto slightly bigger things.

Does he die? No, he gets something of a reunion with his absent father.

Page 5 of 27
Page 5 of 27
This Boy's Life (1993)

This Boy's Life (1993)

You needed to be super skilful with the pause button to glimpse Leo in 1992's Poison Ivy , but he played the lead in This Boy's Life , an adaptation of Tobias Wolff's autobiography.

It's the mid-50s, and Toby's mother seems to have finally found a suitable bloke (De Niro), but optimism soon vanishes as he turns violent and abusive.

Not many nineteen-year-olds could go toe-to-toe with De Niro, but DiCaprio acquits himself admirably. There's also a tiny role for Leo's mate, Tobey Maguire.

Does he die? Well, Wolff went on to write his life story, so go figure.

Page 6 of 27
Page 6 of 27
What's Eating Gilbert Grape (1993)

What's Eating Gilbert Grape (1993)

Leo knocked it out of the park again, with the standout performance in an indie populated with talent (Johnny Depp, Juliette Lewis, John C. Reilly).

Nonchalant Gilbert (Depp) watches his life go by in a small Iowa town, caring for his obese mother and mentally-challenged brother, Arnie (DiCaprio). It's a tough character to pull off, but Leo makes him totally believable, and provides the movie's emotional core.

DiCaprio's performance earned him his first Oscar nod.

Does he die? No, but his mama ain't so lucky.

Page 7 of 27
Page 7 of 27
The Quick and the Dead (1995)

The Quick and the Dead (1995)

After a short ( The Foot Shooting Party ) and an uncredited cameo in a French curio ( Les cent et une nuits de Simon Cinéma ), DiCaprio holstered up for Sam Raimi's surprisingly fun western.

He plays cocky gunsmith 'Kid', a sharpshooter who has something of a hostile relationship with his father John Herod (Gene Hackman). Herod rules the town of Redemption, and every year plays host to a quick-draw competition. Sharon Stone's 'The Lady' is in town with a score to settle.

Does he die? Yes! Leo got a taste for deathbed scenes here, as he's gunned down by his old man.

Page 8 of 27
Page 8 of 27
The Basketball Diaries (1995)

The Basketball Diaries (1995)

Leo was back in serious mode for this one, another autobiographical tale. He plays Jim Carroll, a talented high-school basketball star and occasional poet whose world crumbles when he gets gripped by a heroin addiction.

Another committed performance from DiCaprio (who has solid support from Mark Wahlberg and Lorraine Bracco) can't save this 'drugs are bad, m'kay?' lecture from feeling a little too familiar.

Does he die? Surprisingly not, considering the smack addiction, though the road to recovery ain't easy.

Page 9 of 27
Page 9 of 27
Total Eclipse (1995)

Total Eclipse (1995)

This biopic sees DiCaprio portraying Arthur Rimbaud, an enfant terrible of 19th-century poetry. The film documents his life through the eyes of his erstwhile lover Verlaine (David Thewlis), with a script from Christopher Dangerous Liaisons Hampton (from his own play).

DiCaprio doesn't shy away from the man-love scenes, but the relationship between Rimbaud and Verlaine never convinces, and the film lacks the creative finesse of Rimbaud's ground-breaking poetry.

Does he die? Rimbaud has croaked at the beginning of the film, and his life is reflected upon by Verlaine.

Page 10 of 27
Page 10 of 27
Romeo + Juliet (1996)

Romeo + Juliet (1996)

Playing the archetypal lovestruck teen confirmed Leo's stardom (and sowed the seeds of Leo-mania).

Baz Luhrmann's flamboyant and energetic update of Shakespeare's best-known play still feels fresh and vital 14 years on. DiCaprio and Danes are the movie's beating heart, managing to convey the overwhelming adolescent emotions with conviction and credibility ( Twilight take note). After the flashy, vibrant first half, you'll be sucker-punched by the finale.

Does he die? Well, it is one of Shakespeare's greatest tragedies: the prologue spells out the events to come pretty clearly.

Page 11 of 27
Page 11 of 27
 Marvin's Room (1996)

Marvin's Room (1996)

On his route to stratospheric stardom, Leo took a detour with this so-so tear-jerker. While it constantly threatens to go all movie-of-the-week on us (reunited sisters, bed-ridden father, bone marrow neediness), Marvin's Room manages to stay on the not-too-sickly side of sentimental.

The film's bolstered by performances from lady powerhouses Meryl Streep and Diane Keaton, and Leo, in troubled teen mode again, does fine alongside them.

Does he die? Despite the portentous themes, he survives the 98 minutes unscathed.

Page 12 of 27
Page 12 of 27
Titanic (1997)

Titanic (1997)

Well, you probably know the effect James Cameron's epic had on Leo's career. The biggest movie ever (right up until Cameron returned with Avatar ), it wasn't only Jam-Cam who was king of the world after this.

Despite Titanic's numerous flaws, it's a harsh critic who can watch it without misting up at some of the tender moments or being gobsmacked at the visual spectacle of Cameron's creation.

Does he die? Probably his most famous movie demise, as he freezes and gets plonked into ocean, after letting his beloved float on a hunk of wood.

Page 13 of 27
Page 13 of 27
The Man in the Iron Mask (1998)

The Man in the Iron Mask (1998)

Braveheart -scribe Randall Wallace had a crack at the Dumas tale, which sees Louis XIV (DiCaprio) ruling France, while his goodly twin brother (Leo again) is locked up in a dungeon.

D'Artagnan and the three musketeers set about on a twin-trading mission. The plodding second act of this swashbuckler is something of an energy drain, but there's plenty of fun to be had if you treat it as a light-hearted starry romp.

Does he die? Both the snotty fiend and hard-done-by peasant survive.

Page 14 of 27
Page 14 of 27
Celebrity (1998)

Celebrity (1998)

This hardly-vintage Woody Allen comedy sees Kenneth Branagh (in a role that Allen would have undoubtedly taken himself had he been a few years younger) as a novelist who turns to celebrity journalism when times get tough.

Leo, as a hot young movie star (big stretch, you say), plays it arrogant, impulsive and more than a little hedonistic.

The movie may not be perfect, but DiCaprio certainly makes the most of his 10 minutes' screen time.

Does he die? Nah, despite his destructive temperament he makes it out ok.

Page 15 of 27
Page 15 of 27
The Beach (2000)

The Beach (2000)

After flirting with the lead role in American Psycho (which first choice Christian Bale made his own), DiCaprio snaffled the role of Richard from Ewan McGregor in this Danny Boyle adaptation.

The Beach starts promisingly, with a suitably exciting hunt for the mysterious island paradise, and the cinematography ably captures the tropical environment in all its intoxicating beauty. The film just never really takes off once Richard and his companions settle on the island, and the paradise politics fail to resonate.

Does he die? He lives to return to civilisation.

Page 16 of 27
Page 16 of 27
Don's Plum (2001)

Don's Plum (2001)

Shot five years earlier, this black and white low-budget effort made it to the Berlin Film Festival in 2001, against Leo and fellow cast member Tobey Maguire's wishes.

The pair were involved in making the low-budget drama when they were aspiring young actors, but some studio suits smelled a cash-in when the two best buds had gone stellar.

By all accounts, the film, which saw some cool kids hang out in a diner and shoot the shit, was pretty lame.

Does he die? We're guessing no…

Page 17 of 27
Page 17 of 27
Gangs of New York (2002)

Gangs of New York (2002)

Leo returned to cinemas with a bang in 2002, with a mean double-hander.

Gangs was the first time Leo worked with Martin Scorsese, and it was the start of a beautiful friendship (they've teamed up thrice since). Leo plays Irish immigrant Amsterdam Vallon, who comes to the United States seeking vengeance for his father's death.

Despite an iffy Oirish accent, Leo turns in a decent performance, but is unceremoniously blown out of the water by Daniel Day-Lewis' Oscar-nommed grandstanding.

Does he die? Despite dicing with death, he survives this one.

Page 18 of 27
Page 18 of 27
Catch Me If You Can (2002)

Catch Me If You Can (2002)

Released just a matter of weeks after Gangs , Spielberg's con-man caper couldn't have been more different.

Leo plays Frank William Abagnale Jr, the schoolboy charmster who impersonated pilots, doctors and lawyers during a costly, but good-natured, crime spree.

An ace supporting cast (including Tom Hanks as his FBI pursuer, and Christopher Walken as Frank Sr) is on hand to back up Leo, who deftly channels teen insecurities through the confident crim.

Does he die? He made it through this one too…

Page 19 of 27
Page 19 of 27
The Aviator (2004)

The Aviator (2004)

His second team-up with Marty saw him playing millionaire mogul, aircraft designer and occasional moviemaker Howard Hughes.

Despite being arguably a little young for the role, DiCaprio delivers one of his best performances in this glamorous biopic, finding time to romance Jean Harlow (Gwen Stefani), Katharine Hepburn (Cate Blanchett) and Ava Gardner (Kate Beckinsale).

Does he die? No, but he's pretty mentally frail by the end.

Page 20 of 27
Page 20 of 27
The Departed (2006)

The Departed (2006)

The third Scorsese-DiCaprio collaboration saw Marty take home his long overdue Oscar, and the film also nabbed Best Picture.

Leo (edgy, frenetic) is the undercover cop infiltrating a Boston crime outfit, and Matt Damon (calm, sinister) is the criminal mole in the police force. As the warring factions try to smoke out the rats, tension, and the body count, rises.

Based on Hong Kong thriller Infernal Affairs , this is proof that not all remakes have to be naff.

Does he die? Taken down with a shocking head shot.

Page 21 of 27
Page 21 of 27
Blood Diamond (2008)

Blood Diamond (2008)

An action thriller with a conscience, set during the Sierra Leone Civil War. Leo plays Danny Archer, a mercenary/diamond trader who's in town on the lookout for a mahoosive rock that Solomon (Djimon Hounsou) has found.

Cue much poe-faced sermonising from director Ed Zwick, who's not afraid to lecture while blowing stuff up. Leo and Hounsou make a decent reluctant duo, but the less said about Jennifer Connelly's preachy journo the better.

Does he die? He takes a fatal bullet, but not before he's been able to see the error of his ways.

Page 22 of 27
Page 22 of 27
The 11th Hour (2007)

The 11th Hour (2007)

DiCaprio produced and narrated this eco doc, which bears comparison to Al Gore's An Inconvenient Truth badly.

Sure, Leo looks good in front of a camera, and his heart is in the right place when it comes to these issues. But as the scientific evidence is gradually weakened by the presence of so many crackpot theorists, it's impossible to take this seriously and sustain interest.

Does he die? No, he's still around today.

Page 23 of 27
Page 23 of 27
Body of Lies (2008)

Body of Lies (2008)

We were expecting more when DiCaprio teamed up with Ridley Scott. Leo is horribly bearded as Roger Ferris, a CIA agent in Iraq.

There's no denying Scott knows how to shoot a quality action scene, and DiCaprio has a good rapport with greasy boss-man Russell Crowe (even if most of their exchanges do happen over the phone), but the action quickly turns tiresome without a plot to speak of or any characters (except Mark Strong's shady intelligence man) that demand interest.

Does he die? He's bailed out after some nasty hammer work on his hands.

Page 24 of 27
Page 24 of 27
Revolutionary Road (2008)

Revolutionary Road (2008)

Leonardo was reunited with Titanic co-star Kate Winslet (and Kathy Bates!), although they make an altogether different pair in this one.

Directed by Winslet's then-husband Sam Mendes, Revolutionary Road is a pretty unrelenting look at the marital tensions of a young couple in 50s suburbia: he's unsatisfied with his monotonous job, and she's a failed actress forced to play the housewife part. It's certainly uncomfortable viewing, but great performances make this essential, even if you're only likely to watch it the once.

Does he die? No, it's Kate's turn now.

Page 25 of 27
Page 25 of 27
Shutter Island (2010)

Shutter Island (2010)

Leo's fourth time under the instruction of Scorsese, Shutter Island was the pair's biggest box office opening to date, and Scorsese's highest-grossing film worldwide.

Teddy Daniels (DiCaprio) is a U.S. Marshal investigating an escape at a maximum-security mental institute. The twisty nature of the plotting divided audiences (as did Scorsese's unusually extroverted genre touches). Still it ensured the film would gain healthy DVD interest, as one of those that you just had to watch again.

Does he die? "Which would be worse: to live as a monster, or to die as a good man?" Chilling.

Page 26 of 27
Page 26 of 27
Inception (2010)

Inception (2010)

Leo is back in blockbuster mode, though that's not to say that there will be anything dumb about Inception .

Playing dream-invader Cobb, DiCaprio adds working with Christopher Nolan to his CV, as if he's working through a tick list of all the modern greats.

Combine the brain-melting invention of Memento with the huge-scale thrills of The Dark Knight and you get the idea why Inception will be the movie event of the year.

The movie hits cinemas (regular size and IMAX) on Friday.

Read our Inception review .

Page 27 of 27
Page 27 of 27
Matt Maytum
Matt Maytum
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Matt Maytum is the former Editor of Total Film magazine. Over the past decade, Matt has worked in various roles for TF online and in print, including at GamesRadar+. Bucket-list-ticking career highlights have included reporting from the set of Tenet and Avengers: Infinity War, as well as covering Comic-Con, TIFF and the Sundance Film Festival.

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