Leonardo DiCaprio’s New Co-Star Bromance Reportedly Leaves Tobey Maguire Jealous

Here is a curveball I did not have on my 2025 bingo card: word is Leonardo DiCaprio has quietly drifted from longtime buddy Tobey Maguire and gotten tight with his One Battle After Another co-star Sean Penn. File this squarely under unconfirmed-but-loud gossip until someone says something on the record, but the chatter has been consistent enough to raise eyebrows.

Leo and Tobey: A long run, now a little wobbly?

DiCaprio and Maguire have been close since forever by Hollywood standards, but recent reports say the dynamic has changed. Per RadarOnline, Leo has been spending more one-on-one time with Penn in the past few months — think long dinners and deep-dive conversations — and that new bond has apparently pushed Tobey to the sidelines. Neither Leo nor Tobey has addressed any of this publicly.

"Leo did not expect to click with Sean the way he has, especially since they play enemies in the movie. But Sean is now part of Leo's inner circle."

The friend group shuffle

Leo is famously consistent about his crew — historically that has included Maguire, Lukas Haas, nightlife fixture Richie Akiva, and on-and-off regulars like Kevin Connolly and Jay Ferguson. The current vibe, according to the same reports, looks different. The suggestion is not that there was some dramatic falling out, more that Penn has become a regular fixture and Tobey is, at least for now, less central. One source claims Tobey is bummed about it; the gist is that Leo has chosen to ride this new wave and Tobey is not part of it.

Why now? The movie might actually be part of it

One Battle After Another hit theaters in September 2025 and landed well. DiCaprio plays Bob Ferguson; Penn goes full hard-edge as Colonel Steven J. Lockjaw. Critics and audiences are into the pairing — the film is sitting at 94% on Rotten Tomatoes with an 8/10 on IMDb — and a lot of the praise zeroes in on how the two Oscar winners spark against each other. Fun twist: they rarely shared substantial screen time before this, so the novelty factor is real. The movie is currently available to rent on Apple TV if you want to see what the fuss is about.

Quick recap

• Reports say DiCaprio has grown closer to Sean Penn in recent months after working together on One Battle After Another.
• Tobey Maguire, Leo's decades-long friend, is reportedly feeling sidelined by the new dynamic.
• Leo's usual circle has included Maguire, Lukas Haas, Richie Akiva, with past regulars Kevin Connolly and Jay Ferguson; the current lineup seems to be shifting.
• None of the principals have commented; all of this remains secondhand.
• The film itself released in September 2025, stars DiCaprio as Bob Ferguson and Penn as Colonel Steven J. Lockjaw, and holds a 94% Tomatometer and 8/10 on IMDb.
• You can rent One Battle After Another on Apple TV.

Is this a brief season-of-life reshuffle or a long-term change? Hard to say. If it sticks, it would be one of the bigger rewirings of Leo's circle in years. Did the DiCaprio-Penn team-up live up to the hype for you? Drop your take.