Tobey Maguire and Leonardo DiCaprio

Tobey Maguire and Leonardo DiCaprio both began acting in their early teenage years, and often found themselves competing against each other at auditions. The future stars formed a bond over their shared pursuit — in addition to acting, it appears that they were fond of bowling — and became close friends. They began helping each other get roles, recommending the other for a part when one was cast. (They auditioned for the same roles in the NBC sitcom Parenthood and the film This Boy’s Life. DiCaprio won out both times, but helped Maguire land a role in each project.)

In 2013, at that point both huge movie stars — as successful as Maguire has been, his career has always been eclipsed by Leo’s — DiCaprio and Maguire costarred in the critically acclaimed film adaptation of The Great Gatsby.