A Trail of Heartbreak: Leonardo DiCaprio's Near Misses at Oscar Glory

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For more than 20 years, ET has followed Leonardo DiCaprio over the years as he went through four Best Actor losses at the Academy Awards. As he prepares for another Oscar ceremony this February, ET is looking back at his past four Oscar losses.

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DiCaprio earned his first Oscar nomination at age 22 for the 1993 drama What's Eating Gilbert Grape?, in which he played Johnny Depp's developmentally-challenged younger brother. The film proved to be his breakout role and earned him a nod in the Supporting Actor category, but the award ultimately went to the more seasoned pro, Tommy Lee Jones for his memorable role in The Fugitive.

The actor had to wait more than a decade before he was invited back to the big awards show as an Osacr nominee, but in that time, DiCaprio came into his own. He established himself as an undeniable talent as well as a bankable star with films like Titanic, Catch Me If You Can and Gangs of New York. He was finally nominated for a second time after playing the eccentric business tycoon Howard Hughes in The Aviator. The nod marked his first time being recognized in the Best Actor category, but he fell to Jamie Foxx, who won for his uncanny portrayal of Ray Charles in Ray.

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It wasn't long before the Academy gave DiCaprio another shot at Oscar gold, as he was nominated for portraying an opportunistic Rhodesian diamond smuggler in Blood Diamond. Despite the critical acclaim, the Academy decided it was Forest Whitaker's time to shine. More than two decades after his breakout role in Fast Times at Ridgemont High, the esteemed actor won the Oscar on his first (and so far only) nomination.

DiCaprio was thought to be a frontrunner for his dynamic role as a hedonistic stockbroker in The Wolf of Wall Street, especially after he took home a Golden Globe. In the end, voters sided with the man who won the Globe in the drama category that year, Matthew McConaughey, for his portrayal of an AIDS patient in Dallas Buyers Club.

GoldDerby.com's Tom O'Neil offered a possible explanation as to why the talented actor has been overlooked so often.

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"Leo hasn't won in the past, because he suffers from what experts call 'Slap the Stud Syndrome,'" O'Neil told ET. "It's as if the old men in the Academy say, 'Look, kid, you got the looks; you got the money; you got the chicks. Here's one thing you can't have.' Look at our biggest stars who have never won an Oscar: Johnny Depp, Brad Pitt, Tom Cruise. Are you getting the message?"

This year, DiCaprio is once again an early frontrunner in the Best Actor category, which includes Bryan Cranston, Matt Damon, Michael Fassbender and last year's winner, Eddie Redmayne.

The 2016 Oscars, hosted by Chris Rock, will take place on Sunday, Feb. 28 at the Dolby Theatre in Hollywood, California and will air on ABC.