![Sean Penn and Leonardo DiCaprio (f.l.t.r.) at the Fourth Annual Saint-Tropez Gala of the Leonardo DiCaprio Foundation (LDF), July 26, 2017. © Getty Images for Leonardo DiCaprio Foundation Sean Penn and Leonardo DiCaprio (f.l.t.r.) at the Fourth Annual Saint-Tropez Gala of the Leonardo DiCaprio Foundation (LDF), July 26, 2017. © Getty Images for Leonardo DiCaprio Foundation](https://mediapool.bmwgroup.com/cache/P9/201707/P90270872/P90270872-sean-penn-and-leonardo-dicaprio-f-l-t-r--at-the-fourth-annual-saint-tropez-gala-of-the-leonardo-dica-2253px.jpg)
Sean Penn and Leonardo DiCaprio (f.l.t.r.) at the Fourth Annual Saint-Tropez Gala of the Leonardo DiCaprio Foundation (LDF), July 26, 2017. © Getty Images for Leonardo DiCaprio Foundation
![Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online](https://i.dailymail.co.uk/1s/2019/08/13/21/17241168-7353817-image-a-40_1565726928695.jpg)
Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online
![My Leo Obsession | Leonardo DiCaprio photographed by Bruce Weber for... | Young leonardo dicaprio, Leonardo dicapro, Leonardo dicaprio funny My Leo Obsession | Leonardo DiCaprio photographed by Bruce Weber for... | Young leonardo dicaprio, Leonardo dicapro, Leonardo dicaprio funny](https://i.pinimg.com/736x/b3/3b/27/b33b27bd910f3417edf74a5a428851a7--leonardo-funny-poses.jpg)
My Leo Obsession | Leonardo DiCaprio photographed by Bruce Weber for... | Young leonardo dicaprio, Leonardo dicapro, Leonardo dicaprio funny
![Leonardo DiCaprio strolls along sand with Camila Morrone as couple set to wedIrish Mirror Leonardo DiCaprio an… | Leonardo dicaprio, Leopard print bikini, Leonardo Leonardo DiCaprio strolls along sand with Camila Morrone as couple set to wedIrish Mirror Leonardo DiCaprio an… | Leonardo dicaprio, Leopard print bikini, Leonardo](https://i.pinimg.com/originals/b9/db/eb/b9dbeb5e9e7ee643772106a1aa110e9a.jpg)
Leonardo DiCaprio strolls along sand with Camila Morrone as couple set to wedIrish Mirror Leonardo DiCaprio an… | Leonardo dicaprio, Leopard print bikini, Leonardo
![Leonardo DiCaprio, Alan Faena, and More Support Sean Penn at a CORE Fundraiser in Miami – Africa Pearl Leonardo DiCaprio, Alan Faena, and More Support Sean Penn at a CORE Fundraiser in Miami – Africa Pearl](https://africapearl.com/wp-content/uploads/2021/12/1356722825.jpg)
Leonardo DiCaprio, Alan Faena, and More Support Sean Penn at a CORE Fundraiser in Miami – Africa Pearl
![Star Sightings: Leonardo DiCaprio and Girlfriend Nina Agdal Enjoy Date Night in New York! | Entertainment Tonight Star Sightings: Leonardo DiCaprio and Girlfriend Nina Agdal Enjoy Date Night in New York! | Entertainment Tonight](https://www.etonline.com/sites/default/files/styles/max_970x546/public/images/2015-11/640_leonardo_dicaprio_495919272.jpg?itok=2kpWpHT2)
Star Sightings: Leonardo DiCaprio and Girlfriend Nina Agdal Enjoy Date Night in New York! | Entertainment Tonight
![Leonardo DiCaprio & Camila Morrone Share a Kiss at Dinner With Sean Penn in Italy: Photo 4335273 | Camila Morrone, Leila George, Leonardo DiCaprio, Sean Penn Pictures | Just Jared Leonardo DiCaprio & Camila Morrone Share a Kiss at Dinner With Sean Penn in Italy: Photo 4335273 | Camila Morrone, Leila George, Leonardo DiCaprio, Sean Penn Pictures | Just Jared](https://cdn.justjared.com/wp-content/uploads/2019/08/leo-camila-kiss/leonardo-dicaprio-camila-morrone-august-2019-04.jpg)
Leonardo DiCaprio & Camila Morrone Share a Kiss at Dinner With Sean Penn in Italy: Photo 4335273 | Camila Morrone, Leila George, Leonardo DiCaprio, Sean Penn Pictures | Just Jared
![Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online](https://i.dailymail.co.uk/1s/2019/08/13/21/17241184-7353817-image-m-61_1565727121429.jpg)
Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online
![BENICIO DEL TORO SEAN PENN & NAOMI WATTS 21 GRAMS FILM PREMIERE 60TH VENICE FILM FESTIVAL ITALY 05 September 2003 Stock Photo - Alamy BENICIO DEL TORO SEAN PENN & NAOMI WATTS 21 GRAMS FILM PREMIERE 60TH VENICE FILM FESTIVAL ITALY 05 September 2003 Stock Photo - Alamy](https://c8.alamy.com/comp/H8A9TC/benicio-del-toro-sean-penn-naomi-watts-21-grams-film-premiere-60th-H8A9TC.jpg)
BENICIO DEL TORO SEAN PENN & NAOMI WATTS 21 GRAMS FILM PREMIERE 60TH VENICE FILM FESTIVAL ITALY 05 September 2003 Stock Photo - Alamy
![Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online](https://i.dailymail.co.uk/1s/2019/08/13/21/17241210-7353817-image-a-54_1565727025174.jpg)
Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online
![Leonardo DiCaprio Showers Off After Taking a Swim in Italy!: Photo 4334582 | Camila Morrone, Leonardo DiCaprio, Sean Penn, Shirtless Pictures | Just Jared Leonardo DiCaprio Showers Off After Taking a Swim in Italy!: Photo 4334582 | Camila Morrone, Leonardo DiCaprio, Sean Penn, Shirtless Pictures | Just Jared](https://cdn.justjared.com/wp-content/uploads/2019/08/leo-shower/leonardo-dicaprio-yacht-day-camila-morrone-67.jpg)
Leonardo DiCaprio Showers Off After Taking a Swim in Italy!: Photo 4334582 | Camila Morrone, Leonardo DiCaprio, Sean Penn, Shirtless Pictures | Just Jared
![Leonardo DiCaprio & Camila Morrone Share a Kiss at Dinner With Sean Penn in Italy | Camila Morrone, Leila George, Leonardo DiCaprio, Sean Penn | Just Jared Leonardo DiCaprio & Camila Morrone Share a Kiss at Dinner With Sean Penn in Italy | Camila Morrone, Leila George, Leonardo DiCaprio, Sean Penn | Just Jared](https://cdn.justjared.com/wp-content/uploads/headlines/2019/08/leo-camila-kiss.jpg)
Leonardo DiCaprio & Camila Morrone Share a Kiss at Dinner With Sean Penn in Italy | Camila Morrone, Leila George, Leonardo DiCaprio, Sean Penn | Just Jared
![Dlisted | The Older Men And The Sea: Sean Penn And Leonardo DiCaprio Took A Couple's Yacht Trip With Their Girlfriends Dlisted | The Older Men And The Sea: Sean Penn And Leonardo DiCaprio Took A Couple's Yacht Trip With Their Girlfriends](https://dlisted.com/wp-content/uploads/2019/08/BGUS_1682442_001.jpg)
Dlisted | The Older Men And The Sea: Sean Penn And Leonardo DiCaprio Took A Couple's Yacht Trip With Their Girlfriends
![Leonardo DiCaprio, Sean Penn share a double yacht date in Italy, plus more news | Gallery | Wonderwall.com Leonardo DiCaprio, Sean Penn share a double yacht date in Italy, plus more news | Gallery | Wonderwall.com](https://www.wonderwall.com/wp-content/uploads/sites/2/2018/05/1028015-leonardo-dicaprio-spotted-out-and-about-in-new-york.jpg)
Leonardo DiCaprio, Sean Penn share a double yacht date in Italy, plus more news | Gallery | Wonderwall.com
![Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online Leonardo DiCaprio and Camila Morrone enjoy a double date with Sean Penn and Leila George | Daily Mail Online](https://i.dailymail.co.uk/1s/2019/08/13/20/17241694-0-image-a-11_1565725975615.jpg)