Tina Fey's joke during the Golden Globes in 2014, "And now, like a supermodel's vagina, let's all give a warm welcome to Leonardo DiCaprio," was especially fitting! The Oscar winner has dated everyone from Gisele Bundchen to Naomi Campbell to even Blake Lively! Click through to see all the models and actresses that DiCaprio has courted throughout the years
Party photos surfaced in the late '90s that sugged he "Walked That Way" with the model-actress daughter of Aerosmith frontman Steven Tyler.
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