Tobey Maguire doesn’t like being a third wheel in a friendship. The Spiderman actor is said to be jealous of a reported bromance between Leonardo DiCaprio and Sean Penn.The two Academy Award winners recently worked together on the film One Battle After Another, which came out in September. Since the start of that movie, the two have apparently been thick as thieves, leaving Tobey out in the cold.
Tobey and Leo have been longtime friends, but that friendship “crumbles” with Sean in the picture says a source. Both men co-starred in the 2013 movie The Great Gatsby, where their characters were neighbors.
Sean Penn and Leonardo DiCaprio are reportedly spending a lot of time together, “bumming” Tobey Maguire out

Another idol seems to have replaced Tobey in Leo’s eyes, one with two golden statuettes, Sean Penn. That’s not sitting well with the father of two. “It’s bumming him (Tobey) out, big-time – but right now Leo’s made his choice, and Tobey’s not involved at all,” an insider tells RadarOnline.
According to the insider, Sean demanded one-on-one time with the Titanic actor. They’ve bonded over, among other things, their love for Italian cuisine. For Sean’s presence to drive such a wedge into Leo’s friendship with Tobey suggests the Milk star has made quite the impression. Tobey and Leo have been good friends since childhood.
If there’s any consolation, Tobey may not be the only friend that Leo’s left behind. The Revenant star has apparently distanced himself from Bradley Cooper. The Hangover actor is dating Leo’s ex, Gigi Hadid.
There may be a glimmer of hope for Tobey that his friendship with Leo isn’t completely dead. Reportedly, Leo, along with his girlfriend Vitoria Ceretti, joined Tobey for Thanksgiving last week.
Leo and Sean have known each other casually for years, both through a mutual friend in Robert De Niro. Since 2024, Leo and Sean have been pals, crowding Tobey out of the equation.
TELL US – DO YOU THINK SEAN PENN IS TO BLAME FOR LEO AND TOBEY’S FRIENDSHIP WOES?
