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.
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.
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.
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.
A Reunion to Remember
She'll never let go, Jack! Titanic co-stars DiCaprio and Kate Winslet reunited on the 2016 Oscars red carpet.
Oscar Winner
That same night, DiCaprio won his first-ever Oscar for his work in The Revenant.
A Memorable Moment
The following year, DiCaprio returned to the Oscars to present the award for Best Actress, which went to Emma Stone.