Revisiting Leonardo DiCaprio's Award-Worthy Oscar Appearances

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Leonardo DiCaprio is once again nominated for an Oscar!

The actor, who won his first Academy Award in 2016 for his work in The Revenant, is expected to return to 2020 Oscars ceremony this Sunday, where he’s nominated in the Best Actor category for his role in Once Upon a Time in Hollywood. Prior to his win in 2016, DiCaprio had been nominated in the Best Actor category three times.

In 2005, he received a nod for his work in The Aviator. Two years later, DiCaprio was up for the award for his role in Blood Diamond. Then, in 2014, DiCaprio’s work in The Wolf of Wall Street scored him another Best Actor nod at the award show. DiCaprio received his first-ever Academy Award nomination at the 1994 Oscars, where he was up for Best Supporting Actor for his role in What’s Eating Gilbert Grape.

As we wait to see the actor at the Oscars this weekend, we’re taking a look back at all of his memorable moments at the iconic ceremony over the years.

Check out the gallery below to see DiCaprio’s Academy Award evolution, from his first appearance in 1994 to his win in 2016! And be sure to keep checking back with E! News all weekend to get the latest updates on all things 2020 Oscars!

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First Oscars!

The actor made his first appearance at the Academy Awards in 1994. That year, DiCaprio was nominated for Best Supporting Actor for his role in What’s Eating Gilbert Grape.

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Date Night With Gisele

DiCaprio brought his girlfriend at the time, Gisele Bündchen, as his date to the 2005 Oscars. The actor was up for the Best Actor award for his work in The Aviator.

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Red Carpet Royalty

At the 2007 Oscars, DiCaprio was once again nominated for Best Actor. This time, he received a nod for his role in Blood Diamond.

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His Leading Lady

DiCaprio brought his mom as his date to the 2014 Oscars, where he was up for Best Actor in The Wolf of Wall Street.

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A Reunion to Remember

She’ll never let go, Jack! Titanic co-stars DiCaprio and Kate Winslet reunited on the 2016 Oscars red carpet.

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Oscar Winner

That same night, DiCaprio won his first-ever Oscar for his work in The Revenant.

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A Memorable Moment

The following year, DiCaprio returned to the Oscars to present the award for Best Actress, which went to Emma Stone.

Watch E!’s red carpet coverage of the 2020 Oscars Sunday, Feb. 9 starting at 1 p.m. ET/10 a.m. PT followed by the Oscars telecast at 8 p.m. ET/5 p.m. PT on ABC! And don’t miss the E! After Party special at 11:15 p.m. ET/8:15 p.m. PT for a recap of the 2020 Academy Awards.

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