Entertainment Movies Will He Win Again? A Brief History of Leonardo DiCaprio and the Oscars DiCaprio is nominated for the sixth time this year, and hoping to snag his second win By Julia Emmanuele Published on February 7, 2020 04:10 PM Share Tweet Pin Email 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. A.M.P.A.S/REX/Shutterstock 1994, What’s Eating Gilbert GrapeNominated for: Best Supporting Actor for playing Arnie Grape, the developmentally disabled younger brother of Johnny Depp‘s GilbertAge: 19His Date: His mother, IrmelinLost to: Tommy Lee Jones, for his performance as U.S. Marshal Samuel Gerard in The FugitiveLevel of Heartbreak at His Loss: Jay Gatsby longingly staring across the sound at Daisy Buchanan’s lighthouse 2005, The AviatorNominated 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 1940sAge: 31His Date: Then-girlfriend, Gisele BündchenLost to: Jamie Foxx, for his performance as legendary soul singer Ray Charles in RayLevel of Heartbreak at His Loss: Rose watching Jack freeze to death after the Titanic goes down 2007, Blood DiamondNominated for: Best Actor for his role as Danny Archer, a white Rhodesian gun runner and diamond smugglerAge: 33His Date: His motherLost to: Forest Whitaker, for his performance as Idi Amin, the former President of Uganda, in The Last King of ScotlandLevel of Heartbreak at His Loss: Romeo drinking poison because he thinks that Juliet has died 2014, The Wolf of Wall StreetNominated 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 PictureAge: 39His Date: His motherLost to: Matthew McConaughey, for his performance as Ron Woodroof in Dallas Buyers ClubLevel 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: 41His Date: His mom (again!). He walked the red carpet with his BFF, Kate Winslet, thoughLost 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.