By Julia Hays
10:00 PM PDT, July 1, 2020
See two decades of their cutest moments!
'Titanic' (1997)
20 years ago, audiences fell in love with Jack and Rose.
'Titanic' (1997)
As the movie soared to No. 1 at the box office, a beautiful friendship formed between the lead actors.
1998 Golden Globe Awards
Their friendship's red carpet debut occurred when they celebrated their Titanic award nominations together.
2007 Golden Globe Awards
The pals, this time nominated for their roles in Blood Diamond and The Reader, snapped a quick pic inside the awards ceremony.
2007 Vanity Fair Oscar Party
The twosome may not have taken home Academy Awards that night, but it didn't stop them from sharing a sweet photo op.
'Revolutionary Road' (2008)
A decade after Titanic, the besties reunited for this classic literary adaptation, reminding audiences and critics of their captivating onscreen presence together.
'Revolutionary Road' Movie Premiere
The friends made critics go wild when they reunited in 2008 for the film directed by Kate's then-husband, Sam Mendes.
2009 Golden Globe Awards
Leo was his best friend's lucky charm as she took home awards for both her performances in The Reader and Revolutionary Road.
2009 Golden Globe Awards
The close friends showed their affection with a quick squeeze on the red carpet.
U.K. Premiere of 'Revolutionary Road'
The pair took this red carpet by storm, striking fierce poses for their fans.
2012 Golden Globe Awards
The telecast livened up when the Mildred Pierce star laid a sweet kiss on her friend after his loss.
2016 Screen Actors Guild Awards
The Steve Jobs actress was a supportive best friend to Leo as he began his awards season sweep for his role in The Revenant.
2016 Screen Actors Guild Awards
The Insurgent star made sure to be the first person to congratulate her best friend after his win.
2016 Academy Awards
The only person Leo wanted on his arm the night he took home his first Academy Award was Kate.
2016 Academy Awards
Photographers captured this celebratory hug between the pals during the awards ceremony.
Leonardo DiCaprio Foundation Saint-Tropez Gala
The pair took to the stage to raise money for Leo's charity during the summer of 2017.