David Fisher/Rex USA
Julia Emmanuele
January 14, 2016 09:05 AM

Break out your lucky charms, find a shooting star to wish on and light the candles in front of your Titanic shrine – Leonardo DiCaprio has earned his fifth Academy Award nomination, for playing fur trapper Hugh Glass in The Revenant.

DiCaprio will face off against Bryan Cranston, Matt Damon, Michael Fassbender and Eddie Redmayne for the Best Actor trophy, which would mark his very first Academy Award win.

And after years of fans hoping, wishing, praying (and making jokes) – not to mention some pretty insane role preparation – it seems like 2016 may finally, finally be the year that DiCaprio takes home the trophy. But before we can look ahead to Feb. 28, it seems only right that we take a look back at DiCaprio’s long road to (possible) Oscar glory.

1994, What’s Eating Gilbert Grape
Nominated for: Best Supporting Actor for playing Arnie Grape, the developmentally disabled younger brother of Johnny Depp‘s Gilbert
Age: 19
His Date: His mother, Irmelin
Who He Lost to: Tommy Lee Jones, for his performance as U.S. Marshal Samuel Gerard in The Fugitive
Level of Heartbreak at His Loss: Jay Gatsby longingly staring across the sound at Daisy Buchanan’s lighthouse

2005, The Aviator
Nominated for: Best Actor for his role as Howard Hughes, the obsessive-compulsive tycoon, aviation pioneer and director who was a prominent figure in Hollywood in the 1920s through the 1940s
Age: 31
His Date: Then-girlfriend, Gisele Bündchen
Who Lost to: Jamie Foxx, for his performance as legendary soul singer Ray Charles in Ray
Level of Heartbreak at His Loss: Rose watching Jack freeze to death after the Titanic goes down

2007, Blood Diamond
Nominated for: Best Actor for his role as Danny Archer, a white Rhodesian gun runner and diamond smuggler
Age: 33
His Date: His mother Who He Lost to: Forest Whitaker, for his performance as Idi Amin, the former President of Uganda, in The Last King of Scotland
Level of Heartbreak At His Loss: Romeo drinking poison because he thinks that Juliet has died

2014, The Wolf of Wall Street
Nominated for: Best Actor, for his role as the hedonistic, hard-partying king of Wall Street, Jordan Belfort. As one of the film’s producers, DiCaprio was also up for Best Picture
Age: 39
His Date: His mother Who He Lost to: Matthew McConaughey, for his performance as Ron Woodroof in Dallas Buyers Club
Level of Heartbreak at His Loss: Not nearly as intense as the complete emotional devastation we felt watching Chiwetel Ejiofor lose that year (sorry, Leo)

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