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 ...

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 ...

BFFs Tobey Maguire and Leonardo DiCaprio are more alike than you may think. Not only do they love acting and partying, but they both love dating women under 25 years old. Maguire and DiCaprio have ...

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.

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 ...

Tobey Maguire thought Leonardo DiCaprio’s behavior while auditioning for one of their first film roles would’ve worked against his chances. by Antonio Stallings. Published on February 25, 2023.

Leonardo DiCaprio Jumps Off Yacht While Vacationing with Tobey Maguire in Saint-Tropez . The longtime friends have been enjoying a sun-soaked summer getaway to the South of France ...

Leonardo DiCaprio may be all loved up with girlfriend Vittoria Ceretti, but his close buddy Tobey Maguire is keeping their womanizing flag flying by enjoying no frills fun and vowing he won’t ...

Lukas Haas and Tobey Maguire. Pic credit: LESERmbi / BACKGRID. As it turns out, Camila is not too old to date Leo– yet. Camila Morrone turns 25, fans joke she is too old for Leonardo DiCaprio ...

Taylor said that as people in the crowd started gossiping, they figured out DiCaprio and fellow actor Tobey Maguire were staying at Paws Up Resort for Maguire’s 40th birthday, which was Saturday.

Before Leonardo DiCaprio became the Oscar-winning face of prestige films, and before Tobey Maguire swung into hearts as Spider-Man, both were part of a wild and controversial Hollywood circle ...