Leonardo DiCaprio is almost as well-known for his love life as his movies and activism. Since launching his acting career in the early 1990s, the heartthrob has had a string of high-profile relationships with Hollywood’s finest actresses and, perhaps more famously, younger models.The Oscar winner’s dating history has often made him a punching bag for fellow celebrities including Tina Fey and Ricky Gervais.
While introducing him at the 2014 Golden Globe Awards, the 30 Rock creator quipped, “And now, like a supermodel’s vagina, let’s all give a warm welcome to Leonardo DiCaprio.” Six years later, the Office alum joked at the same awards show, “Once Upon a Time in Hollywood is nearly three hours long.
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