Will He Win Again? A Brief History of Leonardo DiCaprio and the Oscars

After years of fans hoping, wishing, praying (and making jokes) — not to mention some pretty insane role preparation — 2016 was finally, finally the year that Leonardo DiCaprio took home an Academy Award for playing fur trapper Hugh Glass in The Revenant.

This year, he’s up for Best Actor again, this time for his role as Rick Dalton in Once Upon a Time … in Hollywood. This nomination marks Leo’s sixth in total and second possible Oscar win. He’s up against Jonathan Pryce, Antonio Banderas, Adam Driver and Joaquin Phoenix.

Before we can look ahead to Feb. 9, it seems only right that we take a look back at DiCaprio’s long road to 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
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
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
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
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)

2016, The Revenant
Nominated for: Best Actor, for his role as the vengeful frontiersman, Hugh Glass, who gets brutally attacked by a bear and left for dead … but survives against all odds.
Age: 41
His Date: His mom (again!). He walked the red carpet with his BFF, Kate Winslet, though
Lost to: No one! He finally snagged the trophy!
Level of Elation at His Win: Happier than DiCaprio was to never have to sleep in animal carcasses or eat raw bison liver ever again.