This week, Leonardo DiCaprio is heading back to theaters in director Paul Thomas Anderson's One Battle After Another. Since 1991, DiCaprio has appeared in over 30 movies, been nominated for seven Academy Awards and won one Oscar for Best Actor. To celebrate the actor's latest film, Watch With Us has put together our picks for the seven best Leonardo DiCaprio movies, ranked. The common theme between these movies is that DiCaprio is at his best when paired with some of the top directors in Hollywood. Leonardo DiCaprio Says He Feels 32 Despite Being 50, Shares Biggest Regret 7.