19Leonardo DiCaprio and Tobey Macguire
The two even arranged it so they were neighbors at one point, probably as an excuse to just hang out more. The two eventually appeared together in The Great Gatsby, which mined some of their natural charm together on-screen for one of the central friendships of the story.
Leonardo DiCaprio is one of the biggest stars in the world and has been since he was a teenager. He’s been an undisputed icon for years and has been doing anything he wants with anyone he wants. But it might surprise you to learn that a frequent partner of
his during these adventures is the original Spider-Man himself, Tobey Macguire. The pair has actually been friends for over 30 years by this point, meeting one another at an audition when they were both 12.
Their bond has been well-documented, with the two actors often going on vacations together and even going big on some luxury yacht trips. DiCaprio is even considered a member of the family by Tobey, to the point where his children consider him their Uncle Leo. Tobey told People, “They will visit the beach, or grab Sunday brunch. Leo is great with Ruby and Otis… He is very hands-on too, and offers help with cutting up their food and will carry them across the street. He would be a great dad!"