Leonardo DiCaprio and Tobey Maguire in Saint-Tropez, France, on July 26, 2017. Victor Boyko/Getty. Meghan Markle & Katharine McPhee, and More Celebs Who Have Been Friends Since They Were Kids ...

Leonardo DiCaprio yachts with Tobey Maguire, bikini-clad ‘Love Island’ star Arabella Chi in Spain By . Leah Bitsky. Published Aug. 10, 2023, 11:28 a.m. ET. Explore More ...

Leonardo DiCaprio’s friendship with Tobey Maguire has seemingly been his longest relationship to date. The buds met as child actors in the ’80s while they were auditioning for the same roles.

Leonardo DiCaprio and Tobey Maguire are living it up together. The longtime friends were photographed going to Hotel Plaza Athénée in Paris on Wednesday, where they were attending an event with ...

Leonardo DiCaprio and Tobey Maguire are continuing to take in the City of Light. The close friends were photographed together on Thursday night in Paris, dressed casually as they left Hôtel ...

The City of Light — and models. Leonardo DiCaprio was spotted with young beauty Neelam Gill again as the pair stepped out for dinner in Paris with Tobey Maguire. DiCaprio and Maguire left the ...

Maybe Leonardo DiCaprio’s famed Posse is set for a comeback, especially now that his one-time wingman Tobey Maguire has shed marriage and domesticity and appears to be getting back into Posse ...

Leonardo DiCaprio and Tobey Maguire have been best friends for decades — and they have the bling to prove it. The two actors were seen arriving together at Hotel Plaza Athénée in Paris on ...

Tobey Maguire is continuing to third-wheel Leonardo DiCaprio’s lavish summer vacation with girlfriend Vittoria Ceretti in Ibiza, Spain. The trio were spotted relaxing on the sandy shores of the ...

Leonardo DiCaprio and Tobey Maguire starred in a post-“Titanic” experimental indie film called “Don’s Plum” in 1996 that he and co-star Tobey Maguire then reportedly had banned from ever ...

Third-wheeling isn’t a problem for Tobey Maguire. The “Spider-Man” star was spotted out and about with close pal Leonardo DiCaprio and his girlfriend, Vittoria Ceretti, for a day of yachting ...