TJ Martell Music Event, 1989
1989: A 15-year-old Leo already showing a penchant for hats—later, this will devolve into unfortunate newsboy caps, but for now, his beanie is both cute and functional.
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Leonardo Di Caprio attending NBC up front press conference for his 1990 series Parenthood in Los Angeles
1990: A fresh-faced Leo at 16.
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DiCaprio In Classroom From ‘Growing Pains,’ c. 1991.
1991: Leo enters the American mainstream with a recurring role as a homeless kid on “Growing Pains.”
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1992 MTV Rock ‘n’ Jock Basketball
1992: Ball was life for Leo in ’92.
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“Benny & Joon” Los Angeles Premiere
1993: DiCaprio receives his first Oscar and Golden Globe nominations for his role as Arnie in “What’s Eating Gilbert Grape?” alongside Johnny Depp.
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66th Annual Academy Awards
1994: Ah, who can forget mid-’90s Leo with that floppy haircut and middle part?
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“The Basketball Diaries” Premiere – Westwood, California
1995: Leo hits the red carpet sans tie and with a messy bowl cut.
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“Romeo & Juliet” Los Angeles Premiere
1996: With “Romeo + Juliet” costar Claire Danes on the red carpet.
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“Titanic” Hollywood Premiere, 1997
1997: Leo is the cover star of People’s “Most Beautiful” list and for good reason; this is the year that he also loses his flippy hairstyle for a more clean-cut ‘do.
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55th Annual Golden Globe Awards
1998: Jack and Kate forever!
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1999 Comic Relief
1999: With a pre-“Entourage” Kevin Connolly at a theme park. Along with Tobey Maguire, Harmony Korine, David Blaine, and others, they make up the Pussy Posse—the name is pretty self-explanatory.
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“The Beach” – Hollywood Premiere
2000: Leo’s boyish good looks are evolving to a more mature look as he nears 25.
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The Concert for New York City – Backstage
2001: With his “The Basketball Diaries” costar, Mark Wahlberg (you may remember him as Marky Mark).
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Cameron Diaz and Leonardo DiCaprio
2002: Hitting the red carpet with “Gangs of New York” costar Cameron Diaz.
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Catch Me If You Can
2003: Catch him if you can—it’s not hard to see why anyone wouldn’t fall for Leo’s tricks when he looks this dashing.
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“The Aviator” Los Angeles Premiere – Red Carpet
2004: With his “The Aviator” costar Gwen Stefani.
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77th Annual Academy Awards – Arrivals
2005: With Gisele Bündchen, the first of many high-profile, leggy Victoria’s Secret–model girlfriends.
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Warner Bros. Pictures Premiere Of “The Departed” – Arrivals
2006: Leo makes a move to grittier roles with “The Departed,” which solidifies his status as a Scorsese fave.
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2007 Vanity Fair Oscar Party Hosted by Graydon Carter – Inside
2007: Nearly 10 years after Titanic, Leo and Kate are still besties.
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Body Of Lies Paris Photocall
2008: Clean-cut, V-neck-clad Leo—rarely seen but much appreciated.
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Utah Jazz v Los Angeles Lakers, Game 5
2009: Broing out courtside with Tobey Maguire, as one does.
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Celebrities At The Lakers Game
2010: Another day, another supermodel. This time, it’s Bar Refaeli accompanying Leo to the game.
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Hollywood Foreign Press Association’s 2011 Installation Luncheon – Presentation Of Grants
2011: Marky Mark and Leo back at it.
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69th Annual Golden Globe Awards – Arrivals
2012: At 38, Leo proves that he can still clean up quite nicely for the red carpet.
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Opening Ceremony And ‘The Great Gatsby’ Premiere – The 66th Annual Cannes Film Festival
2013: With Tobey Maguire, his costar in “The Great Gatsby.”
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8th Annual Clinton Global Citizen Awards – Arrivals
2014: Even with a man bun and some excessive beard growth, Leo is still a heartbreaker.
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2015
2015: Blue steel at the SAGs.
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NBC’s “73rd Annual Golden Globe Awards” – Show
2016: Is this the year that Leo wins his Oscar? No matter what the outcome, he’ll always be a winner in our hearts.