EXCLUSIVE: Leonardo DiCaprio's Friendship With Tobey Maguire 'Crumbles' While He Grows Close to Sean Penn — as New Pals Spend A lot of Quality Time Together
Leonardo DiCaprio's decades-long friendship with Tobey Maguire 'crumbles' as he and Sean Penn spend quality time together.
Dec. 1 2025, Published 6:15 a.m. ET
Capricious Leonardo DiCaprio has grown tight with his One Battle After Another costar Sean Penn – and now the Titanic stud's longtime buddy Tobey Maguire is unhappy to be playing second fiddle, RadarOnline.com can reveal.
According to sources, DiCaprio, 50, is enjoying long boozy meals with Penn, 65, since wrapping their recently released thriller, but there's no room at the table for any of DiCaprio's usual wingmen – including Spider-Man's Maguire.
Leo And Sean Growing Closer
Sean Penn grows close to Leonardo DiCaprio as Tobey Maguire feels left out of the circle.
"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," an insider said.
"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."
The source explained Maguire, 50, would not be prone to partaking in the heavyweights' feasts because of his "strict" vegetarian diet and added that "food just isn't his love language" the way it is for Penn and DiCaprio.
Maguire Being 'Iced Out'
Bradley Cooper's link to Gigi Hadid adds to DiCaprio's friendship tensions.
"It's bumming him out, big-time – but right now Leo's made his choice, and Tobey's not involved at all," the insider shared.
But this appears to be just the latest friendship drama for DiCaprio.
As RadarOnline.com previously reported, sources said the Revenant Oscar winner has distanced himself from pal Bradley Cooper after the Hangover hunk started dating his supermodel ex-girlfriend Gigi Hadid.
Now it seems Maguire may also be iced out.
Inside Leo's Inner Circle
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DiCaprio and Penn form a new bond, sidelining Maguire.
A source said: "Sean and Leo have known each other casually for many years and had a major mutual pal in Robert De Niro. But 2024 was the year they finally became bros, and that's crowded out Tobey, who is a hard guy to get along with under the best of circumstances.
"I'd say Leo is as surprised by this development as anybody, because he had no expectation of bonding with Sean the way he has – especially since they play bitter enemies-to-the-death in their movie. But Sean is now firmly part of Leo's inner circle, and there's nothing Tobey can do about it."
