By Julia Hays
10:00 PM PDT, July 1, 2020
See two decades of their cutest moments!
'Titanic' (1997)
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/titanic_pz8z9t.jpg?width=1024&quality=80)
20 years ago, audiences fell in love with Jack and Rose.
'Titanic' (1997)
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/titanic_71fa60e3.jpg?width=1024&quality=80)
As the movie soared to No. 1 at the box office, a beautiful friendship formed between the lead actors.
1998 Golden Globe Awards
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-52025253_0.jpg?width=1024&quality=80)
Their friendship's red carpet debut occurred when they celebrated their Titanic award nominations together.
2007 Golden Globe Awards
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-74669958.jpg?width=1024&quality=80)
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
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-76201871.jpg?width=1024&quality=80)
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)
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/revolutionary-road_zcfihx.jpg?width=1024&quality=80)
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
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-84141085.jpg?width=1024&quality=80)
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
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-84248489.jpg?width=1024&quality=80)
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
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-138436827.jpg?width=1024&quality=80)
The close friends showed their affection with a quick squeeze on the red carpet.
U.K. Premiere of 'Revolutionary Road'
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-84348527.jpg?width=1024&quality=80)
The pair took this red carpet by storm, striking fierce poses for their fans.
2012 Golden Globe Awards
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-146037126.jpg?width=1024&quality=80)
The telecast livened up when the Mildred Pierce star laid a sweet kiss on her friend after his loss.
2016 Screen Actors Guild Awards
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-507650270.jpg?width=1024&quality=80)
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
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-507665904.jpg?width=1024&quality=80)
The Insurgent star made sure to be the first person to congratulate her best friend after his win.
2016 Academy Awards
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/GettyImages-512922732.jpg?width=1024&quality=80)
The only person Leo wanted on his arm the night he took home his first Academy Award was Kate.
2016 Academy Awards
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-512959616.jpg?width=1024&quality=80)
Photographers captured this celebratory hug between the pals during the awards ceremony.
Leonardo DiCaprio Foundation Saint-Tropez Gala
![](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2017-12/gettyimages-823379882.jpg?width=1024&quality=80)
The pair took to the stage to raise money for Leo's charity during the summer of 2017.