His role in the dramatic thriller, The Revenant, has positioned him as a presumed favorite in the race for Best Actor at the 88th Annual Academy Awards on Sunday. If DiCaprio does walk away with his first statuette as expected, the win will certainly be all the more sweeter given the numerous losses that have come before it.
As we wait to hear the final results of the Academy's voting, we're looking back at all the times one of the greatest actors in cinematic history had to clap, grin and bare it while watching the coveted honor get handed to someone else.
1994: Best Supporting Actor, What's Eating Gilbert Grape
If DiCaprio seems almost relieved not to hear his name called in the clip, it's for good reason. The 41-year-old actor recently admitted to ET that he wasn't even sure he wanted to win at the time.
"I remember being really paranoid about ever having to go up in front of a billion people," he said. "I didn't quite have the concept that if you ever gave a speech at the Oscars, like a billion people are watching you. As soon as I heard that, I remember saying, 'I really don't want to have a speech even prepared because I don't want to go up there.'"
As they say, be careful what you wish for. The award ultimately went to Tommy Lee Jones for The Fugitive.
2005: Best Actor, The Aviator
More than a decade after his first Oscar nomination, DiCaprio was more sure of himself and had now been upgraded from Best Supporting Actor to Best Actor. And even if he was still reluctant to win, his then-girlfriend, Giselle Bundchen, certainly wanted him to, judging by the look in her eye when he was introduced by presenter Charlize Theron.
In the end, he lost to Jamie Foxx's impeccable portrayal of Ray Charles in the biopic, Ray. The two would later work together in Quentin Tarantino's 2012 western film, Django Unchained.
For his next trip to Hollywood's biggest night, DiCaprio had his mom close by for support when he was overlooked yet again, this time losing to Forest Whitaker for his performance in The Last King of Scotland.
2014: Best Actor, The Wolf of Wall Street
By his fourth acting nomination, it seemed as if fate was coming up with more creative ways to pass DiCaprio up, as his Wolf of Wall Street co-star, Matthew McConaughey, beat him with his performance in Dallas Buyers Club.
As if the loss itself wasn't enough torture, he also had to sit through Jennifer Lawrence's painfully awkward presentation just to not hear his name called once again.