28 Reasons Why Leonardo DiCaprio Has Always Been a Winner in Our Hearts

Cady Lang
28 Reasons Why Leonardo DiCaprio Has Always Been a Winner in Our Hearts
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In recent years, Leonardo DiCaprio has become the de facto face for a certain brand of devil-may-care bad boy: rakishly handsome, shameless womanizer—or, as in Leo’s case, Victoria’s Secret modelizer—and somehow still generally endearing, despite some very poor sartorial choices (newsboy caps, cargo shorts, bushy beard, man bun, and general hirsuteness, among other things) and some semiquestionable lifestyle decisions (vaping at awards shows, playing with water guns topless, leaving the club with ALL of the models).

But Leo wasn’t always the serious actor with a playboy reputation. Once upon a time, his newfound dad bod was a slight, wiry frame, his man bun was a floppy, heavily gelled bowl cut, and his arm candy was nearly nonexistent.

With his first potential Oscar win just around the corner (after countless nominations, no less), we’ve delved deep into the archives for a look back at a younger, fresh-faced DiCaprio and his subsequent evolution into the Leo of present. Even if the Oscar continues to elude him, Leo’s always been a winner in our hearts.

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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.

Photo: Getty

1990: A fresh-faced Leo at 16.

Photo: Getty

1991: Leo enters the American mainstream with a recurring role as a homeless kid on "Growing Pains."

Photo: Getty

1992: Ball was life for Leo in '92.

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1993: DiCaprio receives his first Oscar and Golden Globe nominations for his role as Arnie in "What's Eating Gilbert Grape?" alongside Johnny Depp.

Photo: Getty

1994: Ah, who can forget mid-'90s Leo with that floppy haircut and middle part?

Photo: Getty

1995: Leo hits the red carpet sans tie and with a messy bowl cut.

Photo: Getty

1996: With "Romeo + Juliet" costar Claire Danes on the red carpet.

Photo: Getty

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.

Photo: Getty

1998: Jack and Kate forever!

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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.

Photo: Getty

2000: Leo's boyish good looks are evolving to a more mature look as he nears 25.

Photo: Getty

2001: With his "The Basketball Diaries" costar, Mark Wahlberg (you may remember him as Marky Mark).

Photo: Getty

2002: Hitting the red carpet with "Gangs of New York" costar Cameron Diaz.

Photo: Getty

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.

Photo: Getty

2004: With his "The Aviator" costar Gwen Stefani.

Photo: Getty

2005: With Gisele Bündchen, the first of many high-profile, leggy Victoria's Secret–model girlfriends.

Photo: Getty

2006: Leo makes a move to grittier roles with "The Departed," which solidifies his status as a Scorsese fave.

Photo: Getty

2007: Nearly 10 years after Titanic, Leo and Kate are still besties.

Photo: Getty

2008: Clean-cut, V-neck-clad Leo—rarely seen but much appreciated.

Photo: Getty

2009: Broing out courtside with Tobey Maguire, as one does.

Photo: Getty

2010: Another day, another supermodel. This time, it's Bar Refaeli accompanying Leo to the game.

Photo: Getty

2011: Marky Mark and Leo back at it.

Photo: Getty

2012: At 38, Leo proves that he can still clean up quite nicely for the red carpet.

Photo: Getty

2013: With Tobey Maguire, his costar in "The Great Gatsby."

Photo: Getty

2014: Even with a man bun and some excessive beard growth, Leo is still a heartbreaker.

Photo: Getty

2015: Blue steel at the SAGs.

Photo: Getty

2016: Is this the year that Leo wins his Oscar? No matter what the outcome, he'll always be a winner in our hearts.

Photo: Getty

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