Leonardo DiCaprio Then & Now: Photos

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Leonardo DiCaprio: Then & Now

Leonardo DiCaprio: Then & Now — Leonardo DiCaprio got his start in the film industry by acting in television commercials. He found success after that by playing Luke Brower, a homeless kid who go to know the Seaver family, on ‘Growing Pains.’ Leo acted on the family sitcom for two years, from 1991 to 1992.

Leo got critical acclaim for his acting in ‘What’s Eating Gilbert Grape’ and ‘The Basketball Diaries,’ and tweens and teens alike fell in love with him when he played Romeo in ‘Romeo + Juliet.’ Leo then acted in ‘Catch Me If You Can,’ a fun film about a man who hops between industries, conning people for money.

He has taken on more serious roles in the last decade or so, with his three-film Martin Scorsese streak including ‘Gangs of New York,’ ‘The Aviator,’ and ‘The Departed.’ We personally were huge fans of ‘Inception’ and ‘Shutter Island.’ His latest film, ‘Once Upon a Time in Hollywood,’ pays homage to a long-gone time in the industry. Scroll through to see pics of Leo through the years!

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Leonardo DiCaprio in ‘Growing Pains’ Shirt

Leonardo DiCaprio in ‘Growing Pains’ Shirt — Leonardo DiCaprio was seen here in a ‘Growing Pains’ t-shirt. He acted in the sitcom as Luke Brower, a homeless kid who got to know the Seaver family.

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‘Growing Pains’

‘Growing Pains’ — Editorial use only. No book cover usage.
Mandatory Credit: Photo by Kobal/Shutterstock (5868005c)
Leonardo Dicaprio
Di Caprio, Leonardo – 1991
TV Portrait
Growing Pains

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‘Total Eclipse’

‘Total Eclipse’ — Leonardo DiCaprio posed while in character for ‘Total Eclipse.’ The movie came out in 1995.

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‘Romeo + Juliet’

‘Romeo + Juliet’ — Leonardo DiCaprio was seen here as Romeo in ‘Romeo + Juliet.’ He sat in a patterned shirt and wrote in a journal.

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‘Titanic’

‘Titanic’ — Leonardo DiCaprio was seen here as Jack Dawson in the classic ‘Titanic.’ He looked up at Rose on the stairs in this moment.

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Golden Globes 1998

Golden Globes 1998 — Leonardo DiCaprio and Kate Winslet walked the Golden Globe red carpet together in 1998. Kate wore a Pamela Dennis dress while Leo stunned in a suit.

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‘Catch Me If You Can’

‘Catch Me If You Can’ — Leonardo DiCaprio was seen here filming ‘Catch Me If You Can’ in April 2002. He played a man who conned he way through various careers, including being a pilot.

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Gangs of New York Photocall During 55th Cannes Film Festival Cannes, France – 20 May 2002

Gangs of New York Photocall During 55th Cannes Film Festival Cannes, France – 20 May 2002 — Cameron Diaz and Leonardo Dicaprio posed for pictures for ‘Gangs of New York’ at the Cannes Film Festival on May 20, 2002. Leo wore a simple black suit.

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‘The Aviator’

‘The Aviator’ — Leonardo DiCaprio got out of a plane on set of ‘The Aviator’ while in character. We loved his pilot look!

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‘Earth to LA’ Benefit Concert

‘Earth to LA’ Benefit Concert — Leonardo DiCaprio smiled on the green carpet for ‘Earth to LA,’ which was a charity benefit concert on May 6, 2004. Leo wore a grey suit and a blue shirt.

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Golden Globes 2005

Golden Globes 2005 — Leonardo DiCaprio was seen at a Golden Globes after party at the Beverly Hilton hotel in Los Angeles on Jan. 16, 2005. He gladly sat down after an eventful evening.

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‘Blood Diamond’

‘Blood Diamond’ — Leonardo DiCaprio acted in the 2006 film ‘Blood Diamond.’ He was photographed here on set in character.

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‘The Departed’

‘The Departed’ — Leonardo DiCaprio was photographed while filming ‘The Departed.’ The 2006 flick was directed by Martin Scorsese.

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Academy Awards Vanity Fair Party 2007

Academy Awards Vanity Fair Party 2007 — Leonardo DiCaprio and Kate Winslet intimately posed for a photo together at the Vanity Fairy Academy Awards party on Feb. 25, 2007. We love these two together!

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‘Revolutionary Road’

‘Revolutionary Road’ — Leonardo DiCaprio was photographed in character for ‘Revolutionary Road.’ He acted in the 2008 film alongside actress Kate Winslet.

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‘Revolutionary Road’ Los Angeles Premiere

‘Revolutionary Road’ Los Angeles Premiere — Leonardo DiCaprio posed ont he red carpet for the ‘Revolutionary Road’ premiere on Dec. 15, 2008 in Los Angeles. He played a man in the ’50s who was in a relationship with a woman portrayed by Kate Winslet.

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Golden Globe Awards 2009

Golden Globe Awards 2009 — Leonardo DiCaprio and Kate Winslet reunited on the Golden Globe red carpet in 2009 after acting in ‘Revolutionary Road’ together. They also, of course, starred in ‘Titanic’ decades earlier.

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Thunder vs. Lakers Basketball Game

Thunder vs. Lakers Basketball Game — Leonardo DiCaprio and his friend Tobey Maguire watched the Oklahoma City Thunder play the Los Angeles Lakers. It looked like a great time!

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‘Inception’ Tokyo Premiere

‘Inception’ Tokyo Premiere — Leonardo DiCaprio posed for pics at the premiere for ‘Inception’ in Tokyo, Japan. He looked amazing!

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‘The Wolf of Wolf Street’

‘The Wolf of Wolf Street’ — Leonardo Dicaprio filmed ‘The Wolf of Wall Street’ on August 25, 2012. He played a Wall Street scammer in the film.

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‘The Great Gatsby’

‘The Great Gatsby’ — Leonardo DiCaprio took a photo while in character for ‘The Great Gatsby’ in 2013. He played the titular role.

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Leonardo DiCaprio Portrait

Leonardo DiCaprio Portrait — Leonardo DiCaprio posed for a portrait in New York City on Dec. 15, 2013. He wore a plaid shirt and black blazer.

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Solutions Project Garden Party

Solutions Project Garden Party — Leonardo DiCaprio addressed a crowd at the Solutions Project garden party in New York on June 18, 2015. He had a full beard and wore a cap during his speech.

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88th Annual Academy Awards 2016

88th Annual Academy Awards 2016 — Leonardo DiCaprio posed with his Academy Award on Feb. 28, 2016. Leo looked incrdible in his black suit!

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CinemaCon Photo Call for ‘Once Upon a Time in Hollywood’

CinemaCon Photo Call for ‘Once Upon a Time in Hollywood’ — Leonardo DiCaprio posed for a pic at the CinemaCon Photo Call for ‘Once Upon a Time in Hollywood’ in Las Vegas on April 23. He wore a black outfit with a blue jacket.

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Leonardo DiCaprio & Brad Pitt On ‘Once Upon a Time in Hollywood’ Set

Leonardo DiCaprio & Brad Pitt On ‘Once Upon a Time in Hollywood’ Set — Leonardo DiCaprio and Brad Pitt posed for a picture on set for ‘Once Upon a Time in Hollywood.’ The two A-Listers starred in the movie together.

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‘Once Upon a Time in Hollywood’ Premiere

‘Once Upon a Time in Hollywood’ Premiere — Leonardo DiCaprio looked as suave as ever at the ‘Once Upon a Time in Hollywood’ premiere in Los Angeles on July 22, 2019. He wore a black suit and brown shoes.

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