Leonardo DiCaprio and Tobey Maguire
Though Leonardo DiCaprio and Tobey Maguire portray characters experienced with life in the lap of luxury from time to time (as evidenced by their somewhat recent co-starring in the 2013 version of The Great Gatsby), their upbringing was anything but easy. The two, who were both raised by single mothers, first met at an audition when they were both 12 years old and hoping to get their start in the movie industry. The rest is cinematic (and tabloid) history.
