The Life and Loves of Leonardo DiCaprio

The Finish Line

DiCaprio then starred in the stunning survival epic The Revenant, playing frontiersman Hugh Glass, who was left for dead in the Dakota Territories after a brutal bear attack.

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Viewers watched stunned as DiCaprio’s character struggled across frozen wastelands, injured and alone, in an epic survival story. He also transformed himself physically for the role, growing his hair and a long, wild beard. And the hard work paid off—after an Oscar chase that somewhat mirrored his character’s painful, long struggle through the wilderness, DiCaprio finally reached that coveted trophy, receiving the Academy Award for Best Actor in 2015.

Girlfriends Illustrated

Hot off the heels of his long-awaited Oscar win, DiCaprio now had even more Hollywood clout and critical acclaim than he had before.

Perhaps it was this new accolade that gave him a bit of extra luck in the romance stakes, because, in 2015 and 2016, he dated Sports Illustrated model and D1 golfer Kelly Rohrbach, and was even rumored to have got engaged to her at one point. However, the two split up in 2016, and DiCaprio sought comfort in the arms of Nina Agdal—who also happened to be a Sports Illustrated model!

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