The pair sashayed down the red carpet, reminiscing of the time they arrived hand in hand at an award in Los Angeles in 1998, as they once again matched in all black ensemble.
Winslet looked simple yet stylish in a black off-shoulder dress while DiCaprio spotted a tuxedo.
"OH GOD. I WASN'T PREPARED FOR THIS.#Oscars KATE AND LEO MY PARENTS," a fan wrote on Twitter.
Another tweeted, "Sees a photo of Kate and Leo and immediately plays Celine."
For DiCaprio, 41, the actor hopes sixth time will be the charm as he's nominated for the coveted Best Actor award for his performance in "The Revenant".
He received his first Oscar nomination in 1994 (DiCaprio was 19 at the time) for Best Actor in a Supporting Role in "What's Eating Gilbert Grape."
Winslet, 40, who was nominated in the best supporting actress category for her portrayal in "Steve Jobs", lost to Alicia Vikander ('The Danish Girl').
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