Leonardo DiCaprio drops Tobey Maguire for Sean Penn?

Leonardo DiCaprio's friendship with Tobey Maguire falls apart?

By The News Digital
December 01, 2025
Leonardo DiCaprio drops Tobey Maguire for Sean Penn?
Leonardo DiCaprio drops Tobey Maguire for Sean Penn?

Leonardo DiCaprio and Tobey Maguire's friendship is said to be crumbling as the Titanic star grows close to his One Battle After Another co-star Sean Penn.

Sources recently revealed that DiCaprio has been spending more time with Penn, leaving Maguire feeling sidelined, according to Radar Online.

The source told the outlet, "There is no mistaking the friendship Leo has forged with Sean over the last year and a half."

"Nor can you ignore how Tobey Maguire doesn't participate in this relationship at all, and he and Leo have been friends since they were little kids," they added.

The insider went on to explain, "Sean has demanded – and gotten – a lot of one-on-one time with Leo. They're having long dinners, long conversations, and they've especially bonded over their mutual love of Italian cuisine."

While the Spider Man star feels iced out, insiders claim that DiCaprio has made "his choice."

"It's bumming him out, big-time – but right now Leo's made his choice, and Tobey's not involved at all," the source said.

Leonardo DiCaprio and Tobey Maguire are known to be one of Hollywood's most famous friends. They met as child actors in late 1980s while auditioning for same roles and formed close connection based on their shared experiences.

On the other hand, the Oscar-winning actor developed strong bond with Sean Penn since they started working together on the film One Battle After Another in 2025.