Leonardo DiCaprio’s Road to the Oscars, From ‘What’s Eating Gilbert Grape’ to ‘The Revenant’

Will it finally be his year? Leonardo DiCaprio is the favorite to win at the 88th Academy Awards — and boy, has he waited a long time for that gold statue. The former child star-turned-hunky actor is nominated in the Best Actor category for his stellar performance (he ate a raw bison liver!) in the drama The Revenant.

DiCaprio, 41, has been racking up accolades all season, but has yet to win an Oscar over the course of his 27-year acting career, despite earning four previous nominations. On Sunday, February 28, he will go up against Matt Damon (The Martian), Michael Fassbender (Steve Jobs), Eddie Redmayne (The Danish Girl) and Bryan Cranston (Trumbo).

Before the big night, take a look back at DiCaprio’s Oscar appearances through the years, from the 1990s to now.

What’s Eating Gilbert Grape, 1993
A then 19-year-old DiCaprio earned his first Oscar nomination for his role as disabled teen Arnie Grape in the critically acclaimed drama costarring Johnny Depp. He lost out in the Best Actor in a Supporting Role category to The Fugitive’s Tommy Lee Jones.

Years later, Depp admitted that he “tortured” DiCaprio while on set while attending the Santa Barbara International Film Festival in February 2016. Depp also revealed what it was really like to work with a then-bright-eyed DiCaprio. “He worked really hard on that film and spent a lot of time researching,” he said. “He came to set and he was ready to work hard and all his ducks were in a row.”

Leonardo DiCaprio
Leonardo DiCaprio at the Academy Awards on March 21, 1994 in Los Angeles, California. Barry King/WireImage

Titanic, 1997
Our hearts will go on! DiCaprio’s life changed forever after he played Jack Dawson in Titanic, opposite his now-BFF Kate Winslet. Some critics believed that he was snubbed for not being nominated in the Best Actor category, but the James Cameron-directed movie did win Best Picture in 1998. It also remained the highest-grossing film of all time until Avatar broke its record in 2009. DiCaprio would later say, during a CBS This Morning interview in 2014, that he’s “incredibly proud” of Titanic.

Leonardo DiCaprio
Leonardo DiCaprio attends the “Titanic” Hollywood Premiere on December 14, 1997 at the Mann’s Chinese Theatre in Hollywood, California. Ron Galella, Ltd./WireImage

The Aviator, 2004
Another loss. DiCaprio lost to Ray’s Jamie Foxx in the Best Actor in a Leading Role category in 2005. “I take [acting] so seriously because I just don’t want people to know too much about who I am, because I want to be convincing in the roles that I play,” he told NBC of playing Howard Hughes in the movie at the time.

Leonardo DiCaprio
Leonardo DiCaprio arrives the 77th Annual Academy Awards at the Kodak Theater on February 27, 2005 in Hollywood, California. Frank Micelotta/Getty Images

The Departed, 2006
Bittersweet! DiCaprio wasn’t nominated in the Best Actor category, but the Martin Scorsese-directed drama did win for Best Picture in 2007. The movie also won for Best Director and Best Writing, Adapted Screenplay. The star-studded cast included Damon, Jack Nicholson, Vera Farmiga, Mark Wahlberg, Martin Sheen and Alec Baldwin.

Blood Diamond, 2006
DiCaprio was nominated for Blood Diamond at the 79th Academy Awards in 2007. The gritty film didn’t take home any wins, however, and The Last King of Scotland’s Forest Whitaker took home the Oscar in the Best Actor category.

DiCaprio opened up about the film’s nods shortly after nominations were announced. “I haven’t had the chance to call my family or friends yet. But I’m very excited about it,” he told the Guardian. He joked: “I’m pretty good at the loser face now.”

Leonardo DiCaprio
Leonardo DiCaprio arrives at the 79th Annual Academy Awards in Los Angeles. Alan Benainous/Gamma Press

The Wolf of Wall Street, 2013
Oh, the tears! DiCaprio’s losing streak continued when he lost to Dallas Buyers Club’s Matthew McConaughey in the Best Actor category at the 86th Academy Awards. As a result, #PoorLeo trended via Twitter and memes were created using photos from DiCaprio’s past film roles. One photo of the star at the Dolby Theatre even included the phrase “Always the Bridesmaid, Never the Bride.”

Leonardo DiCaprio
Leonardo DiCaprio arrives at the 86th Annual Academy Awards at Hollywood & Highland Center on March 2, 2014 in Hollywood, California. Steve Granitz/WireImage
Matthew McConaughey & Leonardo DiCaprio
Matthew McConaughey & Leonardo DiCaprio at the 86th Annual Academy Awards at Hollywood & Highland Center on March 2, 2014 in Hollywood, California. Courtesy Photo

The 88th Academy Awards air live on ABC on Sunday, February 28, at 8 p.m. EST.

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