Leo DiCaprio and Tobey Maguire have been buddies. The two of them were together in all their glory in the film The Great Gatsby, and it was like old times – except they were rich and famous now. The two guys met in the late 1980s, when they were both young adolescents who were interested in acting. Their friendship was so cute that they promised to remain loyal to each other and help with the other’s acting career. To this day, it seems that this is the case. When Leo snagged a role on a TV show, he convinced the producers to put Tobey on in a guest role.