That very same year, DiCaprio would find himself inching ever closer to that tantalizing goal of finally securing an Academy Award. His next movie was another Scorsese and Appian Way joint venture, the biographical black comedy The Wolf of Wall Street, based on real-life stockbroker Jordan Belfort’s 2007 memoir of the same name.
DiCaprio starred as Belfort, and the movie followed his exploits as he storms the world of Wall Street by fraudulent means. The movie earned him another Oscar nomination, but still no win—this time losing out to Matthew McConaughey who won for his role in Dallas Buyers Club.
You can imagine how frustrated DiCaprio must have been by this point. Years of fame and fortune in Hollywood, having received so much praise from fans and critics alike—so why was all this achievement not being reflected with an Oscar win?
Fortunately, DiCaprio was able to seek comfort in his new girlfriend, Victoria’s Secret model Toni Garrn. The two of them met in May 2013 and were thought to have dated for about a year before parting ways. Garrn has since gone on to settle down with another actor, Stormbreaker star Alex Pettyfer.