Leonardo DiCaprio & Sean Penn's Friendship Affects Tobey Maguire — Insider

Leonardo DiCaprio and Sean Penn have recently grown closer, causing some tension with Tobey Maguire. The two actors collaborated on Paul Thomas Andersons 2025 film One Battle After Another, which appears to have strengthened their friendship, much to Maguires disappointment.

Radar Online reports that DiCaprios longtime friend, Tobey Maguire, is reportedly unhappy with the actors increasing closeness to Sean Penn. Sources suggest that the Spider-Man star is feeling left out as DiCaprio spends more time with Penn following their film project.

An insider explained, Its clear that Leo has developed a strong connection with Sean over the past year and a half. Tobey isnt part of this dynamic, even though he and Leo have been friends since childhood. The source added that Penn has secured extensive one-on-one time with DiCaprio, sharing long dinners and conversations, and bonding particularly over their shared love of Italian cuisine.

The report also notes a lifestyle difference between the friends: Maguire follows a strict vegetarian diet, which reportedly doesnt align with the way DiCaprio and Penn bond over food. Its frustrating for Tobey, but at this point Leo has made his choice, and Tobey isnt involved, the insider remarked.

Despite this, the friendship between DiCaprio and Maguire seems to remain intact. Maguire was recently seen spending time with DiCaprio and his girlfriend Vittoria Ceretti, including a Thanksgiving meal at Nobu Malibu. Earlier in October, the two were also spotted together at Venice Beach, California.

DiCaprio and Maguire have known each other since childhood, forming a lasting bond over the decades. They previously appeared together in 2001s Dons Plum and the 2013 Baz Luhrmann adaptation of The Great Gatsby.

Author: Sophia Brooks